FRÉSSIGNÉ, C.; GIRARD, 1.L.; DURANDETTI, M...
92
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2) Stereocontrol in Carbolithiation Li A DFT study. The stereocontrol is induced by acetal oxygen lithium coordination. FRÉSSIGNÉ, C.; GIRARD, 1.L.; DURANDETTI, M.; MADDALUNO, J. GP O Br OEt EtO OEt EtO O Li OEt EtO O H 1) n-BuLi (1eq.) 2) THF, -78°C 100% E Angew. Chem. Int. Ed. 891 893 2008 47 - , , 5 , Synthesis of Dendrimer-Like Polymers and Asymmetric and Miktoarm Stars Li Dendrimers up to seventh generation MATMOUR, R.; GNANOU, Y. MVI Br Br Br Br Br Br CH 2 CH Ph CH 2 CH 2 O CH 2 CH Br Br 1) s-BuLi, TMEDA 2) Styrene 3) Ethylene Oxide 4) n J. Am. Chem. Soc. 1350 1361 2008 130 - , , 4 , Chiral Chloro-[D 1 ]methyllithiums of 98% Enantiomeric Excess Li In situ trapping with benzaldehyde KAPELLER, D. C.; HAMMERSCHMIDT, F. MVI Bu 3 Sn OH R 2 R 1 Bu 3 Sn Cl R 2 R 1 n-BuLi Li Cl D H Li Cl H D (R)-[D 1 ] (S)-[D 1 ] PPh 3 , CCl 4 or R 1 = H, R 2 = D R 1 = D, R 2 = H J. Am. Chem. Soc. 2329 2335 2008 130 - , , 7 , Azetine Alkylation Li MACNEVIN, C. J.; MOORE, R. L.; LIOTTA, D. C. CC N N N O Ph Ph N N O Ph O Ph NH O Ph R O Ph NH O Ph R OMe i) LiHMDS, THF, 0°C, 45 min. then RX, 30 min. ii) BzCl, Et 3 N, CH 2 Cl 2 , RT, 1h 6 examples 51 - 71% J. Org. Chem. 1264 1269 2008 73 - , , 4 , 1
Transcript of FRÉSSIGNÉ, C.; GIRARD, 1.L.; DURANDETTI, M...
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Stereocontrol in CarbolithiationLi
A DFT study. The stereocontrol is induced by acetal oxygen lithium coordination.
FRÉSSIGNÉ, C.; GIRARD, 1.L.; DURANDETTI, M.; MADDALUNO, J.
GP
O
Br
OEtEtOOEt
EtO
O
Li
OEtEtO
O
H
1) n-BuLi (1eq.)
2) THF, -78°C100% E
Angew. Chem. Int. Ed. 891 8932008 47 -, , 5 ,
Synthesis of Dendrimer-Like Polymers and Asymmetric and Miktoarm StarsLi
Dendrimers up to seventh generation
MATMOUR, R.; GNANOU, Y.
MVI
Br
Br Br
Br
Br Br
CH2 CHPh
CH2 CH2 O CH2CH
Br
Br
1) s-BuLi, TMEDA2) Styrene3) Ethylene Oxide
4) n
J. Am. Chem. Soc. 1350 13612008 130 -, , 4 ,
Chiral Chloro-[D 1]methyllithiums of 98% Enantiomeric ExcessLi
In situ trapping with benzaldehyde
KAPELLER, D. C.; HAMMERSCHMIDT, F.
MVI
Bu3Sn OH
R2R1
Bu3Sn Cl
R2R1n-BuLi
Li Cl
DH
Li Cl
HD
(R)-[D1] (S)-[D1]
PPh3, CCl4or
R1 = H, R2 = D
R1 = D, R2 = H
J. Am. Chem. Soc. 2329 23352008 130 -, , 7 ,
Azetine AlkylationLi
MACNEVIN, C. J.; MOORE, R. L.; LIOTTA, D. C.
CC
NN
N
O
Ph
Ph
NN
O
Ph
O
Ph
NH
O
Ph
R
O
Ph
NH
O
Ph
ROMe
i) LiHMDS, THF, 0°C, 45 min. then RX, 30 min.
ii) BzCl, Et3N, CH2Cl2, RT, 1h
6 examples 51 - 71%
J. Org. Chem. 1264 12692008 73 -, , 4 ,
1
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of Lentiginosine DerivativesLi
AZZOUZ, R.; FRUIT, C.; BISCHOFF, L.; MARSAIS, F.
CC
N Li
N
OH
OH
H
N
OH
OH
H
N
OH
OH
H
O
O
N
OH
O
O
N
OH
or
or
or
J. Org. Chem. 1154 11572008 73 -, , 3 ,
Ultrasound-Mediated Addition of MeLi-CeCl 3Li
REUMAN, M.; BEISH, S.; DAVIS, J.; BATCHELOR, M. J.; HUTCHINGS, M. C.; MOFFAT, D. F. C.; CONNOLLY, P. J.;RUSSELL, R. K.
CC
NON
NONH2CeCl3 milled - MeLisonication with stirring
THF, -75°C, 1h
Large scale procedure is described.
J. Org. Chem. 1121 11232008 73 -, , 3 ,
Kinetically Stabilized Diphosphene Anion Radical: Synthesis and ReactivityLi
NAGAHORA, N.; SASAMORI, T.; HOSOI, Y.; FURUKAWA, Y.; TOKITOH, N.
MD
P PTBt
TBt
Li
dme, r.t., 8h[Li(dme)3+[TBtPPTBt]
._
TBt = 2,4,6-tris[bis(trimethylsilyl)-methyl]phenyl
dme = 1,2-dimethoxyethane
J. Organomet. Chem. 625 6322008 693 -, , 4 ,
(2-Pyridinyldimethylsilyl)methyllithiumLi
The reaction tolerates metals inside the porphyrin such as (Zn, Cu, Ni).
TAKANAMI, T;. WAKITA, A.; SAWAIZUMI, A.; ISO, K.; O NODERA, H.; SUDA, K.
CC
N
N
NH
NH
R
R
N SiMe2
LiN
N
NH
NH
H
O
R
R
THF, -78°C
then HCl and DDQ
10 examples61-91%
Org. Lett. 685 6872008 10 -, , 4 ,
2
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Cyclic Alkyl TetraynesLi
The tetraynes were not stable but were characterized by NMR, IR and UV-vis.
SPANTULESCU, A.; LUU, T.; ZHAO, Y.; MCDONALD, R.; TYKWINSKI, R. R.
CC
Br
Br
Br
Br
(CH2)n
n-BuLi
hexanes(CH2)n
n = 8-12
Org. Lett. 609 6122008 10 -, , 4 ,
Phosphinamide-Directed Benzylic LithiationLi
ONA BURGOS, P.; FERNANDEZ, I.; IGLESIAS, M. J.; GARCIA-GRANDA, S.; LOPEZ ORTIZ, F.
CC
N
O
R
PhPh2P N
O
R
PhPh2P
E
NH2 Ph
COOH
Me
PhR = Me, Bn,
i) tBuLi, Et2O, -90°C
ii) E+
. HCl
numerous examples 25 - 98%
Org. Lett. 537 5402008 10 -, , 4 ,
Aldol-Polyhalomethyllithium AdditionLi
BOXER, M. B.; YAMAMOTO, H.
CC
OSi(TMS)3 Ph
O
Br3C
OH OSi(TMS)3
Ph+HNTf2 (0.05mol%), ClCH2CH2Cl, -30°C, 15 min.
then CHBr3 (5 eq), THFthen LiTMP (2.5 eq), -100°C, 1h Yield = 70%
Org. Lett. 453 4552008 10 -, , 3 ,
Synthesis and Characterization of Li2(THF) 3[ArNC(SiMe 3)2]Li
Structural data are described.
CHENG, X.; ZHANG, J.; SONG, H.; CUI, C.
LS
NMe3Si
Me3Si Ar 2 Li, THF, 6h, rt NMe3Si
Me3SiLi
Ar
Li
THFTHF
THF1) LiAlH4, H2O
2) nBuLi, Et2O, 15h, rt
NMe3Si Li
Me
HMe3Si
OEt2
Ar = 2,6-iPr2C6H360%
95%
SiAl
Organometallics 678 6822008 27 -, , 4 ,
3
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of Tetrasubstituted Pyrroles by Directed Ortho-Metallation Reactions.Li
Synthesis of tetrasubstituted 2-Aryl-3-arylsulfonyl Pyrroles by regioselective directed ortho-metallation reactions.
BAILEY, N.; DEMONT, E.; GARTON, N.; SEOW, H.-X.
BP
N
SO2
NSO2
DGDGLTMP, n or s-BuLi
I2N
SO2
DGSuzuki
96%I Ar
Synlett 185 1882008 -, , 2 ,
LiNTf 2-Catalyzed Aminolysis of Lactones with Amines.Li
Lithium activation of the carbonyl group is proposed, leading to hydroamide synthesis.
LALLI, C.; TRABOCCHI, A.; MENCHI, G.; GUARNA, A.
BP
O OR2
nR1
LiNTf2 0.5 eq. CHCl3, 85 °C, 40h
NH
R3 R4
1 eq.
R2 NHR3
OH R1 R4
On
64-100%
Synlett 189 1922008 -, , 2 ,
Allylic Sulfonamides Synthesis from ββββ-Alkoxy Aziridines and Organolithium Reagents.Li
MOORE, S. P.; O'BRIEN, P; WHITWOOD, A.C.; GILDAY, J.
BP
R1 MeNTs
OMe
Syn - R1 = Me, n-Pr, i-Pr
R2Li (2.5 eq.), Et2O
-78 °C, 5 min.then r.t. over 1h
R1 MeNTs
OMe
Li
Me
R1
R2
NHTs
H
Z 18-59%
Synlett 237 2412008 -, , 2 ,
Asymmetric Synthesis of Trifluoromethylated PropargylaminesLi
Switchover in diastereoselectivity is studied in accordance with the solvent.
CHEN, X.-Y.; QIU, X.-L.; QING, F.-L.
CC
N
O
R'S
R CF3
R'
NHR
SO
CF3
R'
NHR
SO
Li CF3or 16 examples
67 - 85% toluene or toluene/Me3Alor THF
Tetrahedron 2301 23062008 64 -, , 10 ,
4
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Lithium Cyclopentadienide Li
UEMURA, M.; YORIMITSU, H.; OSHIMA, K.
CC
X
R
R' C CH R'R
X = I, Br, OTf, ONf
R = H, Me, Cl, COOEt, CN, OMe, CF3, naphthyl
R' = nC6H13, cC6H11, Ph, TES, TMS
Pd(OAc)2, PPh3
Cp*Li, THF, ∆
20 examples 58 - 93%
+
Tetrahedron 1829 18332008 64 -, , 8 ,
Four-Component One-pot Synthesis of NitroiminesLi
Mechanism is proposed.
TANAKA, S.; OGUMA, Y.; TANAKA, Y.; ECHIZEN, H.; MASU, H.; YAMAGUCHI, K.; KISHIKAWA, S; KOHMOTO, S.;YAMAMOTO, M.
CC
N
R
R'
R
NO2
2 RCHO + R'CH2NO2 + LiN(TMS)219 examples 29 - 96%
(2 eq) (1 eq) (3 eq)
THF
Tetrahedron 1388 13962008 64 -, , 7 ,
Lithiation of 2-(Chloroaryl)-2-aryl-1,3-dioxolanesLi
PORCS-MAKKAY, M.; KOMAROMI, A.; LUKACS, G.; SIMIG, G.
CC
OO
Cl
R
R'
OO
Cl
R
R'
HOOC
i) nBuLi/PMDTA, THF, -78°C, 20 min.
ii) CO2
Tetrahedron 1029 10332008 64 -, , 6 ,
New Chiral AuxilliaryLi
10 examples, the auxilliary is stable to oxidation, racemization and is reusable.
KATTUBOINA, A.; LI, G.
GP
R
NAux* N Aux*
R
OOMe
BrOLi
OMeP
H
HBu
Bu
O
THF, -78°C, 6h
Aux* :
59-82%de = 80 to >99%
Tetrahedron Lett. 1573 15772008 49 -, , 10 ,
5
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Cyclative Lateral LithiationLi
ALIYENNE, A.O.; KRAÏEM, J.; KACEM, Y.; BEN HASSINE, B.
GP
SN
O
R
O
O O SN
RO O
O
OH1) LDA-TMEDA
THF, -20°C
2) NH4Cl
5 examples69-79%
Tetrahedron Lett. 1473 14752008 49 -, , 5 ,
DithianyllithiumsLi
TANG, S.; HAN, J.. HE, J.; ZHENG, J.; HE, Y.; PAN, X.; SHE, X.
GP
OR
Li
R'S
S R'
SSOH R
+
Et2O-HMPA
-50°C to r.t.
8 examples69-80%
Tetrahedron Lett. 1348 13512008 49 -, , 8 ,
Ireland-Claisen RearrangementLi
A novel route to β2,3-amino acids.YLIOJA, P.M.; MOSLEY, A.D.; CHARLOT, C.E.; CARBERY, D.R.
GP
NOO
ORO N
O
O O
OMe
LiHMDS (2eq.)TMSCl, THF, -78°C
then TMSCHN2, MeOH
6 examples48-79%
anti/syn >95:5 with R=Ph
Tetrahedron Lett. 1111 11142008 49 -, , 7 ,
Birch Reduction of Hexaphenyl- and PentaphenylbenzeneNa
X-ray crystallography and NMR spectroscopy study of the reduction products.
GREALIS, J. P.; MÜLLER-BUNZ, H.; ORTIN, Y.; CONDELL, M.; CASEY, M.; MCGLINCHEY, M. J.
CM
H
R
PhPh
Ph Ph
Ph
Ph
HH
Ph
H
Ph
H H
PhPhPh R = Ph
Birch reduction
R = H
Birch reductionH
H
Ph
H
H
H H
PhPhPh
HH
HH
H
H
H
HHH
Chem. Eur. J. 1552 15602008 14 -, , 5 ,
6
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of dihydroxyphosphinates from Phosphinoyl Ketones.Na
ROJAS-CABRERA, H.; HERNÁNDEZ-PÉREZ, J. M.; HÔ, M.; HERNÁNDEZ-FERNÁNDEZ, E.; ORDÓÑEZ, M.
BP
Ph PPh2
OTBS
O O
Ph PPh2
OTBS
OH O
Ph PPh2
OTBS
OH ONaBH4/MeOH Zn(BH4)2/THF
(S)95%, 95:5, anti:syn 90%, 4:96, anti:syn
Zn
Tetrahedron Asymm. 161 1662008 19 -, , 2 ,
Carbometalation of CyclopropenesMg
The cyclopropylmetals can be trapped with a variety of electrophiles to generate highly substituted cyclopropanes.
YAN, N.; LIU, X.,; FOX, J. M.
OS
C6H13
OH OHC6H13
Ph
PhMgBr (4 equiv.)+
CuI(30 mol%)PBu3 (1.2 equiv.)
-78 °C to rt, THF
83% (96% syn)
Cu
J. Org. Chem. 563 5682008 73 -, , 2 ,
Additions to αααα,ββββ-Unsaturated 2-Pyridyl KetonesMg
Investigation of the utility of a pyridine-based achiral template in enantioselective conjugate radical additions.
SIBI, M. P. ; YANG, Y.-H.
OS
N
O
N
O
N
O
Ph
N
O
Ph
Mg(NTf2)2/Ligand(1 equiv.)
i-PrI, Bu3SnH, Et3B, O2
CH2Cl2, -78 °CLigand :
85% ee : 50% (S)
Zn
Synlett 83 882008 -, , 1 ,
Allylation of Aldehydes with AllyltributylstannaneMg
This magnesium-catalyzed allylation addition is mild, efficient, operationally simple and highly selective.
ZHANG, X.
OS
Cl
CHO
SnBu3
OH
Cl+
MgI2.(OEt2)n
CH2Cl2, rt, 3 h
95%
Synlett 65 682008 -, , 1 ,
7
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of 1-(4-Fluorophenyl)-2-(4-pyridyl)cyclopentene from Cyclopentanone.Mg
ABU THAHER, B.; KOCH, P.; DEL AMO, V.; KNOCHEL, P.; LAUFER, S.
BP
F
O NdCl3.2LiClthen pyMgCl.LiCl (2 eq.)
F
HO
N
F
NNd
Synthesis 225 2282008 -, , 2 ,
N-Protected Bromomethylindoles with Aryl/Alkyl Grig nardMg
The mechanism of the unusual dimerization reaction is presented.
RAMESH, N.; PRAKASH, C.; SURESHBABU, R.; DHAYALAN, V.; MOHANAKRISHNAN, A. K.
PL
N
R2
X
R1
X = Br, ClR1 = SO2Ph, COPh, R2 = H, Me, SPh, CN
N
R2
R1
N
R2
R11.2 equiv PhMgCl
rt, 5-8h
20-71%
Tetrahedron 2071 20792008 64 -, , 9 ,
Grignard Reagents toward Fluoroalkylated EstersMg
A mechanism by computational technique is proposed.
YAMAZAKI, T.; TERAJIMA, T.; KAWASAKI-TASKASUKA, T.
PL
Rf OEt
O
Rf Ph
O
Rf Ph
OH1) PhMgBr (1.1 eqiv)toluene, -80°C, 1h
2) 0°C, rt or 80°C
+
Rf = CF3, CClF2, CHClF, CCl3, CH3, CF3CF2 0-96% 0-84%
Tetrahedron 2419 24242008 64 -, , 10 ,
Synthesis of Substituted FluorenesMg
DONG, C.-G.; HU, Q.-S.
PL
R1
R2
Cl
X
RBrMg
R1
R2 R
3% Pd(OAc)2
THF, 60°C, 20h+
59-93%
R1, R2 = H, Me, OMe, X = Br, I, ClR = H, Me
Pd
Tetrahedron 2537 25522008 64 -, , 11 ,
8
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Chiral Non-Racemic S-Mesityl SulfiniminesMg
SASRAKU-NEEQUAYE, L.; MACPHERSON, D.; STOCKMAN, R. A.
PL
NTsS+
O
Ph
O-
S+
N
R'
O-
Mes1) MesMgBr, THF, -78°C2) LHMDS, rt
3) R'CHO, Ti(OEt)4
R' = alkyl, substituted phenyl, heterocycle
35-60%E.e. >99%
Ti
Tetrahedron Lett. 1129 11322008 48 -, , 7 ,
Ca (ηηηη2222-Ph2CNPh)(hmpa)3 as an Alternative to Yb(II) CatalystCa
Effective catalyst in the dehydrogenative silylation of amines and alkynes
BUCH, F.; HARDER, S.
PB
Ca
NPh
Ph
hmpahmpahmpa
hmpa
Organometallics 5132 51352007 26 -, , 21 ,
Hydrophosphination of Carbodiimides with Heavier Group 2 CatalystsCa
CRIMMIN, M.R.; BARRETT, A.G.M.; HILL, M.S.; HITCHCOCK, P.B.; PROCOPIOU, P.A.
PB
R1
N
N R2
R1
NH
R2
P(R3)2
+ HP(R3)2
MN(SiMe3)2 (2-10 mol%)
rt
M = Ca, Ba, Sr
BaIr
Organometallics 497 4992008 27 -, , 4 ,
Regio- and Stereoselective Friedel–Crafts Alkenylation of Arenes with Alkynes Sc
Terminal alkynes used. Intramolecular version, mechanistic investigations, and recycling presented.
YOON,M.Y.; KIM, J.H.; CHOI, D.S.; SHIN, U.S.; LEE, J.Y.; SONG, C.E.
AF
Ar H Ph R1Ar
R1 H
R2
Sc(OTf)3 or Hf(OTf)4(10 mol %)
[BMIM][SbF6]85 °C, 15 min - 29 h 38 - 96 %
(E)/(Z): 1/99 to 13/87
+Ar = C6H6, p-xylene, mesitylene, Me5-benzene, naphtalene, chlorobenzeneR1 = Me, Ph, CO2Et, CO2Me
YHfYbLuIn
Adv. Synth. Catal. 1725 17372007 349 -, , 10 ,
9
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
3,4-Selective Polimerization of IsopreneSc
LI, S.; MIAO, W.; TANG, T.; DONG, W.; ZHANG, X.; CUI, D.
LS
PN
NSc
OSiMe3 [B(C6F5)4]
AliBu3
P
HN
NSc
Al
Me3Si
n
[B(C6F5)4]
LnLuSiAl
Organometallics 718 7252008 27 -, , 4 ,
Cationic Rare-Earth-Metal Complexes for Controlled Trans-1,4-Isoprene Polymerization.Y
These systems combine high activity and high regio- and stereoselectivity.
ZIMMERMANN, M.; TÖRNROOS, K. W.; ANWANDER, R.
GR
Ln
MeMeMeAl
MeAl
AlMe
MeLn
Me
C6F5C6F5
C6F5
C6F5
C6F5
MeMe
Al MeC6F5
Cp*Ln(AlMe4)2cationizing agent
poly(isoprene)
up to 99.5% transIP 1.16-8.95
isolatedsingle-componentcatalyst (X-Rays)
LaNd
Angew. Chem. Int. Ed. 775 7782008 47 -, , 4 ,
Amidation of Aldehydes by Lanthanide Amido ComplexesLa
A catalytic cycle is proposed.
SEO, S. Y.; MARKS, T. J.
VWP
Ar H
O
+ NH
R2R1 5 mol % La[N(TMS)2]3
C6D6, rt, 24 hAr N
O
R2
R1
23 - 98%
10 examples
Org. Lett. 317 3192008 10 -, , 2 ,
Friedel-Crafts Reaction of Indoles to NitroalkenesCe
Practical synthetic procedures; solvent-free conditions.
BARTOLI, G.; DI ANTONIO, G.; GIULI, S.; MARCANTONI, E.; MARCOLINI, M.; PAOLETTI, M.
GJ
NH
NO2
Ph
NH
NO2
Ph
+CeCl3.7H2O
NaI, SiO2rt, 8 h
96%
Synthesis 320 3242008 -, , 2 ,
10
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
A Ring Size-Selective Reduction of Lactones Using SmI 2 and H2OSm
DUFFY, L. A.; MATSUBARA, H.; PROCTER, D. J.
OC
O
MeHO
O
MeHO
O
O
+ O
MeHO
O
+
MeHO
HO
HO
SmI2
THF, H2O
86% recovered 85% yield
J. Am. Chem. Soc. 1136 11372008 130 -, , 4 ,
Ytterbium Amides as Catalyst for Addition of Amines to NitrilesYb
WANG, J.; XU, F.; CAI, T.; SHEN, Q.
VWP
R C N + H2N R15 mol % 1
Tol, 100 °C, 24 hR C
N
NH2
R1
N N
N
Ph
N
Ph
SiMe3Me3SiYb
ArNH DME
Ar = 2,6-Me2C6H3
1
Org. Lett. 445 4482008 10 -, , 3 ,
Highly Efficient Ethylene/Cyclopentene Copolymerization Ti
Alternating polymer.
LIU, J.; NOMURA, K.
AF
+"Ti"
MAOx1-x Ti
NCl
Cl
"Ti":
1.99 - 3.16 x 104 kg polymer / mol Ti / h
Al
Adv. Synth. Catal. 2235 22402007 349 -, , 14-1
,
Hydrazido Complexes of Early Transition Metals: A Source of MetallanitrenesTi
A highlight
MINDIOLA, D. J.
CY
[M] NNPh2 [M] N
Ph2N
N–N bond Scission
ZrHf
Angew. Chem. Int. Ed. 1557 15592008 47 -, , 9 ,
11
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Dimethylamino-Functionalised and Aryl-Substituted Titanocene Anti-Cancer AgentsTi
The titanocene compounds show high cytotoxicity against LLC-PK indicating their high potential as anticancer agents.
PAMPILLON, C.; CLAFFEY, J.; STROHFELDT, K.; TACKE, M.
PL
Me2NLi
2
Me2NTi
NMe2
Cl
Cl
TiCl4
THF, 20h reflux
O
O OO
O
O
80 %
Eur. J. Med. Chem. 122 1282008 43 -, , 1 ,
Preparation of 2,2-Bis(aryl)cyclopentanonesTi
SEO, J. W.; KIM, H. J.; LEE, B. S.; KALZENELLENBOGEN, J. A.; CHI, D. Y.
BPH
Ar Ar'
O O+ TiCl4 (3.1 equiv)
Zn (6.2 equiv)
(2 equiv)(1 equiv) THF, ref luxAr Ar' Ar Ar'
Oand/or
minor major
Zn
J. Org. Chem. 715 7182008 73 -, , 2 ,
Air- and Moisture-Stable Catalyst in Selective Aldol ReactionTi
Many other examples
SCHETTER, B.; ZIEMER, B.; SCHNAKENBURG, G.; MAHRWALD, R.
BPH
Ph
Me
O
Ph H
O+
Ph
Me
OOH
Ph
Cat : Ti4(µ-BINOLato)6(µ3-OH)4
cat (0.02 equiv)
regioselectivity > 95:5d.e. > 95:5
neat78%
J. Org. Chem. 813 8192008 73 -, , 3 ,
Ti-Catalyzed Reformatsky ReactionTi
ESTEVEZ, R. E.; PARADAS, M.; MILLAN, A.; JIMENEZ, T.; ROBLES, R.; CUERVA, J. M.; OLTRA, J. E.
BPH
R'
O
R H
O+
R'
OOH
R
Cp2TiCl2 (0.2 equiv)
Mn (8 equiv)
(1 equiv) (2 equiv)
THF
Collidine (8 equiv)TMSCl (4 equiv)
X
up to 94%
Mn
J. Org. Chem. 1616 16192008 73 -, , 4 ,
12
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Ti and Zr Complexes of 1,4-di-tert-butyl-1,4-diazabuta-1,3-diene (R-DAB)Ti
Synthesis, X-ray structures and reactivity of R-DAB Group 4 complexes
BENJAMIN A.C.; FREY A.S.P.; GARDINER M.G.; RASTON C.L.; SKELTON B.W.; WHITE A.H.
GN
MCl
ClTi
Cl
N
N
tBu
tBu
ZrN
N
tBu
tBu
M = Ti, Zr
Zr
J. Organomet. Chem. 776 7802008 693 -, , 4 ,
Group 4 Metal Olefin Polymerization Catalysts Stabilized by Bidentate O,P LigandsTi
LONG, R.J.; GIBSON, V.C.; WHITE, A.J.P.
AN
ROMOM
1) nBuLi2) PR'2Cl
3) 5M HCl4) NH3 (aq)
ROH
PR'2
NaH
THF
RO-Na+(THF)
PR'2
1/2 MCl4(THF)2
RO
PR'2
MCl22M = Ti, Zr, Hf
ZrHf
Organometallics 235 2452008 27 -, , 2 ,
Study on Stereoselectivity of Ti-Mediated CyclopropanationTi
Explanation for the origin of cis-diastereoselectivity is proposed.
KANANOVICH, D.; KULINKOVICH, O. G.
CC
R'COOHR' R"
OHi) Ti(OiPr)4
ii) R"CH2CH2MgX
Tetrahedron 1536 15472008 64 -, , 7 ,
Enantioselective Reductive Cyclizations of DiiminesTi
VAIRAPRAKASH, P.; PERIASAMY, M.
TJ
NAr
NAr
NHHN
Ar Ar[Ti*]/Zn
OTi
N
R
R
O
R PhPh
ClO
Cl
R = H, t-BuR' = Ph, PhCH2
Ar = Ph 4-MeO-C6H4
Yield = 45-75%ee = 50-97%
Tetrahedron Lett. 1233 12362008 49 -, , 7 ,
13
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Epoxide Rearrangement - Alkynylation SequenceZr
Several examples
ALBERT, B. J.; KOIDE? K.
BPH
AgRR'
O+
Cp2ZrCl2 (1.2 equiv)
AgOTf (0.5 equiv)(1.6 equiv) CH2Cl2, rt(1 equiv)
R'
OH
R
up to 88%
Ag
J. Org. Chem. 1093 10982008 73 -, , 3 ,
Enforced ηηηη1-Fluorenyl and Indenyl Coordination to ZirconiumZr
OULIE, P.; FREUND, C.; SAFFON, N.; MARTIN-VACA, B.; MARON, L.; BOURISSOU, D.
AN
PPh2 Ph2P H
ArN3
RT, 2h
Ph2PN
Ar
Ph2P
NAr
Ph2PNH
Ar
H
++ +
Ar = Ph, DIPP, Mes
Organometallics 6793 68042007 26 -, , 27 ,
Isolation and Synthetic Applications of 2,5-Bis(alkynylsilyl) ZirconacyclopentadienesZr
LIU, J.; ZHANG, W.-X.; GUO, X.; HOU, Z.; XI, Z.
AN
R2Si
R1
R1
0.5 equiv. Cp2ZrBu2
Tol., 50 °C, 1 hZrCp2
R1
R1
R2Si
R2Si
R1
R1
R = Me, R1 = PhR = Ph, R1 = PhR = Me, R1 = PrR = Me, R1 = Bu
Organometallics 6812 68202007 26 -, , 27 ,
Mono-, Di-, and Trinuclear Complexes Featuring the New Bis(phosphido) Ligand [POP]Zr
TURCULET, L.; MCDONALD, R.
AN
OO
PCl ClP
OP P
Zr
Me2N NMe2
1) sec-BuLi, TMEDA
2) tBuPCl2
Rh
Organometallics 6821 68262007 26 -, , 27 ,
14
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
A Zirconium (1-Pyridinio)imido Complex: Facile N-N Bond Cleavage and N-C FormationZr
HERRMANN, H.; LLORET FILLOL, J.; WADEPOHL, H.; GADE, L.H.
AN
N
Zr NMe2
NMe2
N
N
TBS
TBS
N NH2
+ OTf_
pyridine
N
Zr
N
N
N
TBS
TBS
N
OTf
py
N
Zr
N
N
N
TBS
TBS
N
C
py
C CLiPh
TBS = tBuMe2Si
CPh
Organometallics 172 1742008 27 -, , 2 ,
Isolation and Characterization of Bromination Products of Zr(C5H5)2Br 2Zr
GLÖCKNER, A.; ARIF, A.M.; ERNST, R.D.
AN
Zr(C5H5)2Br2 + 3Br2 Zr(C5H5)Br3 + C5H5Br5
Organometallics 327 3332008 27 -, , 3 ,
Synthesis of Optically Pure 2-Substituted PyrrolidinesZr
10 examples, yields: 40-68%.
AHARI, M.; JOOSTEN, A.; VASSE, J-L.; SZYMONIAK, J.
GJ
OH
N
Pr
PhOH
N
Ph
PrOH
N
Ph
Pr
Br
a) Cp2Zr(H)Cl, CH
2Cl
2
b) Et3N, I
2
Zn or In
64%
ZnIn
Synthesis 61 682008 -, , 1 ,
Zr-Catalyzed Intramolecular HydroaminationZr
KIM, H.; LIVINGHOUSE, T.; LEE, P. H.
CC
NZr(NMe2)2
NP(S)(iPr)2
P(S)(iPr)2
N
R
R
R
R
R
( )n
3
2
2
1
NH2
R
R
R
R
R
( )n
1
2
2
3
4
C6D6, 75°C, 1.5 - 10 h
catalyst ZrL4 (5 mol%)
7 ExamplesNMR Yields = 90 - 98%
catalyst ZrL4 :
Tetrahedron 2525 25292008 64 -, , 11 ,
15
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
New Synthesis of 1,1,4,4-Tetrabromo-1,3-butadienes Zr
ZHANG, H.-J.; SONG, Z.; WANG, C.; BRUNEAU, C.; XI, Z.
TJ
R SiMe3
R SiMe3
Cp2Zr(II)+
+ZrCp2
RSiMe3
RSiMe3
BrBr
R
R
SiMe3
SiMe3
BrBr
R
R
Br
Br
NBSCuCl Br2, -78 °C
CH2Cl2
-78 °C to rt
R = Bu, Hex, Ph20-92%
Tetrahedron Lett. 624 6272008 49 -, , 4 ,
Carboxylation of Propane into Butyric Acids V
Variation of the catalytic conditions, mechanistic study.
KIRILLOVA, M.V.; DA SILVA J.A.L.; DA SILVA, J.J.R.F.; PALAVRA, A.F.; POMBEIRO, A.J.L.
AF
+ COCa[V{ON(CH(CH3)COO)2}2] O
OHOH
O+
K2S2O8TFA (5 mL)80 °C, 20 h
S/V = 66600TON = 18.4 x 10 3
15 % 9.8 %8.5 atm 20 atm
Adv. Synth. Catal. 1765 17742007 349 -, , 10 ,
Synthesis of Chiral Pyridyl AlcoholsV
20 examples; two-step catalytic approach.
HELLER, B.; REDKIN, D.; GUTNOV, A.; FISCHER, C.; BONRATH, W.; KARGE, R.; HAPKE, M.
GJ
O
H
OTMS
HCN
a) [CoCp(cod)], C2H
2 OH
HN
b) MeOH, Bu4NF (cat)
V
t-BuO
t-Bu
N
t-Bu O
t-Bu
N
O
94% (ee 81%) 91 (ee 82%)
TMSCNCH2Cl2, rt, 24 h
catalyst(0.1 mol%)
catalyst
(S) (S)
(R,R)(0.5 mol%)
CoTi
Synthesis 69 742008 -, , 1 ,
Niobium(0)-Catalyzed C-C CouplingNb
FUCHIBE, K.; MITOMI, K.; SUZUKI, R.; AKIYMA, T.
PG
CF3 NbCl5 (30 mol%)LiAlH4 (6 equiv)
Dioxane, refluxR R' R R'
15 examples, 54-92% yield
Chem. Asian J. 261 2712008 3 -, , 2 ,
16
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Alkynyl Fischer Carbene ComplexesCr
First synthesis of E-dithiafulvene thione or dithioesters
GRANADOS, A. M.; FRACAROLI, A. M.; DE ROSSI, R. H.; FUERTES P.; TORROBA, T.
RF
SS
S
RS+ Ph
Cr(CO)5
OMe
1) Et2O, -40°C
2) Al2O3 S
SR1
SR2
Ph
H
Chem. Commun. 483 4852008 -, , 4 ,
Fischer Carbene ComplexesCr
Three-, five-, six- and seven-membered rings are easily available
AZNAR, F.; FANANAS-MASTRAL, M.; ALONSO, J.; FANANAS, F. J.
RF
OMe
R NiPr2
R2
R'
(CO)5Cr +
Chem. Eur. J. 325 3322008 14 -, , 1 ,
Arenetricarbonylchromium Complexes: New LigandsCr
New ligands extending the range of “Danisphos” ligands, with central and planar chirality
ALBERICO, E.; BRAUN, W.; CALMUSCHI-CULA, B.; ENGLERT, U.; SALZER, A.; TOTEV, D.
RF
(OC)3Cr
PPh2
PR'2(OC)3Cr
PPh2
NMe2
OMeCr(CO)3
PPh2
NMe2
MeO
Eur. J. Inorg. Chem. 4923 49452007 -, , 31 ,
Arenetricarbonylchromium Complexes:photochemical Substitution of N2 and H2Cr
KAYE, S. S.; LONG, J.R.
RE
O O
O O
[Zn4O(BDC)3]
Cr(CO)6H2, hν
O O
O O
Cr(CO)3
O O
O O
Cr(CO)2
H2
N2
O O
O O
Cr(CO)2
N2
J. Am. Chem. Soc. 806 8072008 130 -, , 3 ,
17
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Carbene Complexes 3 + 2 Cycloaddition/ NiCr
[M] = Cr(CO)5
BARLUENGA, J.; BARRIO, P.; RIESGO, L.; LOPEZ, L. A.; TOMAS M.
RF
MeO[M]
R1R2
R3
Ni(COD)2
SiO2
O
R1
R2
R3
+
J. Am. Chem. Soc. 14422 144262007 129 -, , 46 ,
Carbene Complexes: Total Synthesis of Phomactin B2Cr
HUANG, J. H.; WU, C.; WULFF, W. D.
RE
(CO)5CrOP
HHO
OO
phomactin B2
J. Am. Chem. Soc. 13366 133672007 129 -, , 44 ,
Olefin And Alkyne TrimerizationCr
AGAPIE, T.; LABINGER, J. A.; BERCAW, J. E.
RE
[Cr]+ [Cr]+
C2H4
J. Am. Chem. Soc. 14281 142952007 129 -, , 46 ,
Modified Ferrite-based Catalysts for WGS ReactionCr
Relationship between temperature-programmed reduction profile and activity
KHAN, A.; SMIRNIOTIS, P. G.
CM
Fe3+
Fe2+H2O
H2
CO2
CO
Mn+
M = Cr, Mn, Co, Ni, Cu, Zn, Ce
MnCoNiCuZnCe
J. Mol. Catal. A 43 512008 280 -, , 1-2,
18
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Carbene Complexes and Thiolate IonsCr
BERNASCONI, C. F.; PERZ-LORENZO, M.; CODDING, S. J.
RE
ArOCr(CO)5
Ph+ RS-
RSCr(CO)5
Ph+ ArO-
J. Org. Chem. 9456 94632007 72 -, , 25 ,
Carbene Complexes: NHCCr
X = Cl, Br, I, PF6
KIM, S.; CHOI, S.Y.; LEE, Y. T.; PARK, K. H.; SITZMANN, H.; CHUNG, Y. K.
RE
(CO)5Cr=OMe
Ph+ NN
RR'+
X-
tBuOK
THF, 70°C, 2hN N RR'
(OC)5Cr
J. Organomet. Chem. 5390 53942007 692 -, , 24 ,
Fischer Carbene Complexes With Silyl-Substituted AlkynesCr
LI, Z.; MOSER, W. H.; ZHANG, W.; HUA, C.; SUN, L.
RF
(CO)5Cr=OMe
R'+ R2 TIPS
C6H6
reflux, 24hTIPS
CO R'
OMe
R2
and/orO
OMe
R'R2
TIPS
33<Y<73%
J. Organomet. Chem. 361 3672008 693 -, , 2 ,
Arenetricarbonylchromium, Arenetricarbonylmanganese ComplexesCrMn
First synthesis of Cr and Mn complexes linked to nucleosides M= Cr(CO)3 or +Mn(CO)3ETHEVE-QUELQUEJEU, M.; TRANCHIER, J. P.; ROSE-MUNCH, F.; ROSE, E.; NAESENS, L. DE CLERCQ, E.
RE
HN
N
O
O
O
OR
RO
M
M = Cr(CO)3 +Mn(CO)3
Organometallics 5727 57302007 26 -, , 23 ,
19
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Carbene : Fischer Type CarbenesCr
synthesis of nitrogen containing heterocyclic analogues of arylnnaphthalene lignads
JANA, G. P.; GHORAI, B. K.
RE
N
O
R
SiMe3
(CO)5Cr
Me
OMe
NR'
O
O
N
NR'
COMe
RO
OR' = Me, Ph
aq. HCl
Tetrahedron 12015 120252007 63 -, , 48 ,
Intermolecular Dötz BenzannulationCr
IRVINE, S.; KERR, W.; MCPHERSON, A. R.; PEARSON, C.M.
RF
(CO)5CrOMe
R1 R2+
CH2Cl2
Ce(IV), HNO3
O
R1
R2
Oup to 92% yield
Tetrahedron 926 9352008 64 -, , 5 ,
Arenetricarbonylchromium Complex: Radical Aromatic SubstitutionCr
BYERS, J. H.; NEALE, N. R.; ALXANDER, J. B.; GANGEMI, S. P.
RF
(OC)3Cr
tBuLi
propylene oxideBu4NI, Na2S2O3
CH2Cl2, hν
tBu
Tetrahedron Lett. 7903 79052007 48 -, , 44 ,
Diimido-Bridged Dimolybdenum ComplexesMo
PAL, K.; SARKAR, S.
RF
SMo
SO
Na
NC O
OO
SMo
S
CN
CN
2-
SMo
SO
NC
NC N
N SMo
S
CN
CN
2-S
S
NH2
SH
Eur. J. Inorg. Chem. 5333 53442007 -, , 33 ,
20
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Molybdovanadophosphoric Acid Modified ZirconiaMo
Synthesis by an incipient wetness impregnation method, tested on the hydroxylation of phenol
PARIDA, K. M.; MALLICK, S.
CM
OH OH OH
OH
OH
+"ZMVPA"
H2O, H2O2
V
J. Mol. Catal. A 104 1112008 279 -, , 1 ,
Phosphomolybdic Acid-supported Silica Gel Mo
Efficient and cost-effective solid acid for the benzylation of indoles with benzylic alcohols
YADAV, J. S.; SUBBA REDDY B. V.; SRINIVAS REDDY, A.
CM
NH
NH
OH
PMA/SiO2
DCE, 80°C+
J. Mol. Catal. A 219 2232008 280 -, , 1-2,
Cyclopentadienyl Heteropolynuclear M-Sn ComplexesMo
CHEN, S. S.; SONG, H. B.; TANG, L. F.
RF
O
NPh2
O
NPh2
O
NPh2
Na M(CO)6
Ph2SnX2
NaM(CO)3 M(CO)3XPh2Sn
W
J. Organomet. Chem. 5763 57682007 692 -, , 24 ,
Heterocyclic Carbene ComplexesMo
LE BIHAN, Y. Y.; FAUX, N.; CARO, B.; ROBIN-LE GUEN, F.; LE POUL, P.
RF
O
O
R R
CH3SO3CF3
CH3(OCH3)CW(CO)5NEt3
W(CO)5
MeO
OR R
J. Organomet. Chem. 5517 55222007 692 -, , 24 ,
21
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
CyclocarbonylationMo
X= O, NTs, CH2... Synthesis of bicyclic lactams in 67 - 91% yield
KIM, S. H.; KANG, E. S.; YU, C. M.
RF
X
C
N NPhth
X
C
NNPhth
OH
H
Mo(CO)6
DMSO, CH2Cl2
100°C, 6h
Synlett 2439 24412007 -, , 15 ,
CyclocarbonylationMo
KIM, S. H.; KANG, E. S.; YU, C. M.
RF
X
C
N NPhth
Mo(CO)6
DMSO, 100°C, 6hX
N
O
NPhth
67-91%
Synlett 2439 24412007 -, , 15 ,
Acetylation of Alcohols, Phenols, and AminesMo
26 examples, yields: > 87%; solvent-free conditions.
KADAM, S.T.; KIM, S.S.
GJ
OH OO
CH3
H3[P(Mo3O10)4].nH2O (0.2 mol%)
Ac2O, rt, 2 min97%
Synthesis 267 2712008 -, , 2 ,
Selective Terminal Alkyne MetathesisW
COUTELIER, O.; NOWOGROCKI, G.; PAUL, J.-F.; MORTREUX, A.
AF
C5H11 H
W2(NMe2)6/(HOC(Me2)CH2OMe)(4 mol % in situ)
C5H11 C5H11 H H+toluene
80 °C, 1 h87 % conv, 65 % metathesis
Adv. Synth. Catal. 2259 22632007 349 -, , 14-1
,
22
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Alkyne MetathesisW
One of the most active homogeneous catalyst for alkyne metathesis
BEER, S.; HRIB, C. G.; JONES, P. G.; BRANDHORST, K.; GRUNENBERG, J.; TAMM, M.
RE
W
C
CMe3
NN
N
tBu
But
OC
CH3
F3C
F3C
OC
H3CF3CF3C
Angew. Chem. Int. Ed. 8890 88942007 46 -, , 46 ,
Hydrido(hydrosilylene)tungsten ComplexesW
R’ = Me, Et exo-anti isomer only quantitative rt
WATANABE, T.; HASHIMOTO, H.; TOBITA, H.
RF
R'
(CO)2WSi
HC(SiMe3)3H
R2 R3
OR'
(CO)2W
R3
R2(SiMe3)3C-SiH2-O
J. Am. Chem. Soc. 11338 113392007 129 -, , 37 ,
Tungsten Pentacarbonyl ComplexesW
Synthesis of nitrogen-containing bicyclic compounds
ONIZAWA, Y.; KUSAMA, H.; IWASAWA, N.
RF
NMs
TIPSO
R'
R H R
N
H
TIPSO MsR'
MsN
TIPSO
R'
R HW(CO)5L
n-Bu3
W(CO)5L
Hvinylidene pathway π-alkyne pathway
J. Am. Chem. Soc. 802 8032008 130 -, , 3 ,
Selective Oxidation of Sulfide Catalyzed by Peroxotungstate with Aqueous H2O2W
catalyst immobilized on ionic liquid-modified silica
SHI, X.-Y.; WEI, J.-F.
CM
O
OO Si N N
PF6
CH2Cl2 : CH3OH, 30% H2O2, rtR
SR' R
SR'
O
R S R'
O
O
or
W2O3(O2)42-
J. Mol. Catal. A 142 1472008 280 -, , 1-2,
23
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Mn(III)(salen)-catalyzed Synthesis of Cyclic Organic CarbonatesMn
“supercritical” CO2, homogeneous and immobilized Mn-salen complexes
JUTZ, F.; GRUNWALDT, J.-D.; BAIKER, A.
CM
O
R
OO
R
O
Mn(salen) catalyst
CO2
J. Mol. Catal. A 94 1032008 279 -, , 1 ,
Catalase Mimics of a Manganese(II) ComplexMn
Study on the effect of axial ligands and pH
KAIZER, J.; CSAY, T.; KŒVÁRI, P.; SPEIER, G.; PÁRKÁNYI, L.
CM
Mn(indH)Cl22 H2O2 2 H2O + O2
indH = 1,3-bis(2'-pyridylimino)isoindoline
J. Mol. Catal. A 203 2092008 280 -, , 1-2,
Photochromic Materials Based on Linkage IsomerizationMn
Thermal isomerization: activation enthalpy = 21.4 kcal/mol and entropy = 3.5 eu.
TO, T. T.; DUKE III, C. B.; JUNKER, C. S.; O'BRIEN, C. M.; ROSS II, C. R.; BARNES, C. E.; EDWIN WEBSTER, C.;BURKEY, T. J.
HJR
MnOC
CO
N
O
MnOC
CO
N
O
hν, heptane, r. t.
∆, dark, < 10 min
Purple blue
Organometallics 289 2962008 27 -, , 2 ,
Ortho-Directed Lithiation/Electrophilic Quench SequenceMn
Calculations: C2 lithiated intermediate eclipsed by a Mn-CO bond most favored intermediate.
JACQUES, B.; CHANAEWA, A.; CHAVAROT-KERLIDOU, M.; ROSE-MUNCH, F.; ROSE, E.; GERARD, H.
HJR
MnOC
CO
CO
Ph
H
MeO
MnOC
CO
CO
Ph
H
Me OMe3Si
THF, -78 °C / nBuLi, 15 min.; Me3SiCl, 1 h
86%
Li
Organometallics 626 6362008 27 -, , 4 ,
24
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
ηηηη5- and ηηηη6-Complexes Having Double Bond Conjugated with the ππππ-Systems.Mn
Aromatization gives Cationic η6-arene Complex with C=C conjugated with the π-system.CETINER, D.; TRANCHIER, J.-P.; ROSE-MUNCH, F.; ROSE, E.; HERSON, P.
HJR
Mn
CO
H
H
MeO
CHO
CH3 Th
CO
CO
Mn
CO
H
H
MeO
CTh
CO
CO
H2C
OTh
CH3
H
CH2Cl2, HBF4.OMe2, -35 °C, 1.5 h +
Yellow crystals, 45% 40 %
Organometallics 784 7882008 27 -, , 4 ,
Metal-Mediated Retro Diels-Alder of Dicyclopentadiene DerivativesTc
Same reaction with Re
LIU, Y.; SPINGLER, B.; SCHMUTZ, P.; ALBERTO, R.
MVI
O
HNCOOH
OCHNgly NH
O
OH
O
TcOC
COCO
[99mTcO4]- or [99mTc(OH2)3(CO)3]+
Re
J. Am. Chem. Soc. 1554 15552008 130 -, , 5 ,
Resolution of Planar-Chiral Derivatives of 4-(Dimethylamino)pyridineFe
Safer and effcient preparation of the racemic mixture described. A second example is given.
WURZ, R.P.; LEE, E.C.; RUBLE, J.C.; FU, G.C.
AF
N
N
FeMe Me
Me MeMe
resolution
2 crystallizations with di-p-toluoyltartaric acid
(-)-1 (> 99% ee; 37 %)(+)-1 (> 99 % ee; 38 %)
Adv. Synth. Catal. 2345 23522007 349 -, , 14-1
,
Iron Complexes for Asymmetric Hydrogenation of Polar BondsFe
SUI-SENG, C.; FREUTEL, F.; LOUGH, A.J.; MORRIS, R. H.
AE
R1 R2
X OH
H
O
R1 R2
HX H
+ +Cat. [Fe] /KOtBu
RT18-76% ee
*N
PPh2
Fe
L
N
PPh2
N
MeC
2+
L = CO, CNtBu
**
Angew. Chem. Int. Ed. 940 9432008 47 -, , 5 ,
25
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Multiple Aromatic Amination Mediated by a Diiron Co mplexFe
AVENIER, F.; GOURÉ, E.; DUBOURDEAUX, P.; SÉNÈQUE, O.; ODDOU, J.-L.; PÉCAUT, J.; CHARDON-NOBLAT, S.;DERONZIER, A.; LATOUR, J.-M.
AE
NN O
Z
N
N
N
Fe
OO
Fe
O O
R
O
ON
2+
S
Angew. Chem. Int. Ed. 715 7172008 47 -, , 7 ,
Desulfinylative C-C Cross-Coupling Reaction of Sulfonyl Chlorides Fe
RAO VOLLA, C. M.; VOGEL, P.
AE
R-SO2Cl + R'MgX R-R' + SO2 + Mg(Cl)X[Fe(acac)3] (cat.)
THF/NMP, 80°C (30 examples, yield : 6-82%)
Angew. Chem. Int. Ed. 1305 13072008 47 -, , 7 ,
Asymmetric Allylic Alkylation of Acyclic Amides wit h Pd-Catalyzed Fe
ZHANG, K.; PENG, Q.; HOU, X.-L.; WU, Y.-D.
AE
FeN
O
iPr
P
NEt2
OR
NR32
O
R1
R2
OAc
R4
+ R4
NR32
O
R2
R1
R1 = alkyl, Ph, OR R2 = H, Me ; R3 = Ph, Me, R4 = H, Me
11 examplesyield 75-99%ee 73-93%
Pd(C3H5Cl)2, (S, Sphos, S)-L (2 mol%)
LiHMDS (100 mol%)LiCl (100 mol%), THF, RT
(S, Sphos, S)-L
Angew. Chem. Int. Ed. 1662 16672008 47 -, , 9 ,
Cycloisomerization and Cycloaddition Reactions Catalyzed by Iron Complexes.Fe
Preparative and mechanistic aspects are detailed.
FÜRSTNER, A; MAJIMA, K.; MARTÍN, R.; KRAUSE, H.; KATTNIG, E.; GODDARD, R.; LEHMANN, C.W.
BP
[Fe0] ate complex
X
R
X
R
H
H Alder-ene
X
R
X
R
[5+2]50-97% 54-99%
(5 to 10 mol%)
J. Am. Chem. Soc. 1992 20042008 130 -, , 6 ,
26
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Polymer Supported Oxidation CatalystFe
Better catalysts for phenol oxidation and cyclohexene epoxidation than unsupported complexes
GUPTA, K. C.; SUTAR, A. K.
PLA
O
N N
O
Me MeNH
NH
M
PP
M = Fe(III)/Cu(II)/Zn(II)
P-HPHZ-M =
CuZn
J. Mol. Catal. A 173 1852008 280 -, , 1-2,
Enantioselective Functionalisation of a PentamethylazaferroceneFe
ANDERSON, J. C.; OSBORNE, J. D.; WOLTERING T. J.
AE
NFe
NFe
R
i) (-)-sparteine/s-Buli, -78°C, ZnCl 2
ii) Pd(PPh3)4 (5 mol%), R-X, PhMe, 110°C
R = I, Ph2COH, TMS, Me, SPh, PPh2, Ar, heteroAr, vinyl
yield = 61-77%, 77-80% ee
Org. Biomol. Chem. 330 3392008 6 -, , 2 ,
Synthesis of Triarylmethane Derivatives Catalyzed by FeCl3Fe
LI, Z.; DUAN, Z.; KANG, J.; WANG, H.; YU, L.; WU, Y.
PL
CHO
X
OMe
Br
OMe
Br
Br
MeO
X
+
FeCl3 10 mol%
Ac2O, 80°C, 22h
59-90%
Tetrahedron 1924 19302008 64 -, , 8 ,
Fe-Catalyzed Homo-Coupling of Aryl Grignard ReagentsFe
LIU, W.; LEI , A.
PL
MgBr
R R R
O26 mol% FeCl3/12 mol% 2,2'-bipyridine
THF, rt, 10 min 74-91 %
Mg
Tetrahedron Lett. 610 6132008 48 -, , 4 ,
27
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Acylation of Ferrocene with Acyl Chlorides in the Presence of Zinc OxideFe
A great variety of acyl chloride (16 reagents) has been used.
WANG, R.; HONG, X.; SHAN, Z.
PL
Fe FeR
O
+ RCOClZnO
1:1:3 molar ratio of ferrocene, ZnO, acyl chloride
reflux CH2Cl25-30 min
Yields from 45 to 96%
Zn
Tetrahedron Lett. 636 6392008 48 -, , 4 ,
Fe(Cp)2PF6 Catalyzed Strecker Reactions of Ketones and AldehydesFe
KHAN, N. H.; AGRAWAL, S.; KURESHY, R. I.; ABDI, S. H. R.; SINGH, S.; SURESH, E.; JASRA, R. V.
PL
R1 R2
O
+ R NH2 + TMSCNFe(Cp)2PF6 (5 mol%)
rt, neat, 20 min R1 R2
NHRNC
R = Ph, PhCH2R1= substituted arylR2 = Me, Et, Ph
68-94%
Tetrahedron Lett. 640 6442008 48 -, , 4 ,
Organoiron-Mediated Synthesis of (±)-MesembrineFe
ROE, C.; SANDOE, E. J.; STEPHENSON, G. R.; ANSON, C. E.
PL
Fe(CO)3
MeO
OMe
OMe
Fe(CO)3 PF6
MeO
OMe
OMeCN
O
OMe
OMe
NMe
Na(Me3SiCH2CH2O2CCHCN)THF, 0°C
then TBAF, THF, reflux
77%
(±)-mesembrine
Tetrahedron Lett. 650 6532008 48 -, , 4 ,
FeCl3-Catalyzed Amidation Reaction of Secondary Benzylic and Allylic AlcoholsFe
Direct substitution of various amides such as benzamide, sulfonamide, acetamide and acrylamide is reported
JANA, U.; MAITI, S.; BISWAS, S.
PL
R1
OH
+ R2 NH2R1
NHR2
FeCl3 (5 mol%)
CH3NO2
R1 = alkyl, aryl, allylR2 = PhCO, Ts, CH3CO, CH2=CHCO
55-98%
Tetrahedron Lett. 858 8622008 48 -, , 5 ,
28
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Recyclable Water-Soluble Fe(II)/EDTA Complex as CatalystFe
BHOR, M. D.; BHANUSHALI, M. J.; NANDURKAR, N. S.; BHANAGE, B. M.
PL
R1
HN
R2
R3
R4
O
R3
R4 R1
N
R2
+ H2O+1 mol Fe(II)/EDTA-Na2
water, 400psi H2, 150°C, 12 h
R1, R2, R3, R4 = alkyl, aryl, heterocycle 21-88%
Tetrahedron Lett. 965 9692008 48 -, , 6 ,
Preparation of Amidoalkyl NaphtholsFe
This solvent-free procedure offers advantages such as shorter reaction times and recovery and reusability of the catalyst.
SHATERIAN, H. R.; YARAHMADI, H.
PL
CHO
OHR
OH
HN
O
CH3
RR = H, Cl, F, OMe, NO2, Me
FeCl3.SiO2 (catalyst)
method A or B+
method A : CH3CNmethod B : CH3CONH2
for A : 65-84%
for B : 77-93%
Tetrahedron Lett. 1297 13002008 48 -, , 8 ,
Fast Transfer Hydrogenation of AldehydesRu
Aromatic, aliphatic, and unsaturated aldehydes reduced.
BARATTA, W.; SIEGA, K.; RIGO, P.
AF
O
R H+
OH 1 (0.05 - 0.01 mol %)
K2CO3 (1 - 10 mol %)82 °C, 20 s to 5 min
TOF up to 5.0 x 105 h-1
OH
R HH
O+
N
NH2
RuCl
P
PPh2
Ph2
1:
Adv. Synth. Catal. 1633 16362007 349 -, , 10 ,
Monosilylated Recyclable Catalyst for MetathesisRu
Several catalysts prepared. Diene and enyne substrates reacted. Efficient catalyst recycling.
ELIAS, X.; PLEIXATS, R.; WONG CHI MAN, M. MOREAU, J.J.E.
AF
Ph Ph
O
OPhPh
"Ru" 9c(3.5 mol % in Ru)
anh. CH2Cl2r.t., 4.5 h
5 recyclings from > 98 % to 90 % conv.
(9c: 0.139 mmol Ru / g)
RuO
Cl Cl
N
NMes
Mes
O OHN
O
SiO1.5 . x SiO2
9c:
Adv. Synth. Catal. 1701 17132007 349 -, , 10 ,
29
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Hoveyda–Grubbs Catalysts bearing Modified N-Heterocyclic Carbene LigandsRu
Comparison in ring-opening metathesis polymerization , ring-closing metathesis and cross metathesis reactions.
LEDOUX, N.; LINDEN, A.; ALLAERT, B.; MIERDE, H.V.; VERPOORT, F.
AF
O
Ru
PCy3 N NCy Cy
Ru
O
Cl
Cl
ClCl
N NR
Ru
O
Cl
Cl
R = Me, Cy
N NR
Ru
O
Cl
Cl
R = Me, Cy, iPCamp
Adv. Synth. Catal. 1692 17002007 349 -, , 10 ,
Activation of sp2 Carbon-Hydrogen Bonds by a Ruthenium (II) ComplexRu
FOLEY, N. A.; GUNNOE, T. B.; CUNDARI, T. R.; BOYLE, P. D.; PETERSEN, J. L.
AE
NH2
O
O
+ CH3CN[Ru] Ru
PMe3
N
MeN
N
NB
H
N
N
NCMe
Angew. Chem. Int. Ed. 726 7302008 47 -, , 4 ,
Aqueous-Phase Fischer-Tropsch Synthesis with a Ruthenium Nanocluster CatalystRu
XIAO, C.-X.; CAI, Z.-P.; WANG, T.; KOU, Y.; YAN, N.
AE
CO + H2 Hydrocarbon + H2ORu nanoclusters
100-150°C3 MPa, H2O
Angew. Chem. Int. Ed. 746 7492008 47 -, , 4 ,
Efficient C-H Bond Amidation Catalyzed by Ru(II) Porphyrin ComplexesRu
CHANG, J. W. W.; CHAN, P. W. H.
AE
R H
O10 mol% [Ru]
R NHTs
O
IPh NTs
20 examples60-99% yield
Y
X
Y
Y
Y
N N
NN
Y
YX
Y
Y
Y Y
X
YYY
YX
Y
Y
Ru
X = Me, Y = HX = Y = F
CO
[Ru] :
Angew. Chem. Int. Ed. 1138 11402008 47 -, , 6 ,
30
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
O-allylation of Alcohol Catalyzed by a Planar-Chiral Cyclopentadienyl Ru ComplexRu
ONITSUKA, K.; OKUDA, H.; SASAI, H.
AE
R1 Cl + R2OH R1
OR2
*O
O
Ph2P
RuMeCN
MeCN
tBu
+
PF6-
Cat. [Ru] 3 mol%
K2CO3, THF 30°C, 24h 15 examples,
yield >91%, 95% eebranched/linear >20:1
Cat. [Ru] :
Angew. Chem. Int. Ed. 1454 14572008 47 -, , 8 ,
Asymmetric Hydrogenation of Acyl Silanes Catalyzed by Ru(II) ComplexesRu
ARAI, N.; SUZUKI, K.; SUGIZAKI, S.; SORIMACHI, H.; OHKUMA, T.
AE
Ar2P
PAr2
Ru
NH2
N
RR
Cl
Cl
R1 Si
O
R2R1 Si
OH
R2
H2, (S)-Ru cat.
15 examples, yield : 54-99%> 99% ee
(S)-Ru cat. :
Angew. Chem. Int. Ed. 1770 17732008 47 -, , 9 ,
Asymmetric Transfer Hydrogenation.Ru
Various aminoalcohols and additives have been tested.
XU, Z.; MAO, J.; ZHANG, Y.; GUO, J.; ZHU, J.
MJ
Ph
O
[RuCl2(p-cymene)]2(0.0125 eq.)
HCO2Na (5 eq.)H2O, rt
OH
NHR
Ph
OH(0.03 eq.)
R = H S, 72;5% eeR = Ts R, 81.5% ee
Catal. Commun. 618 6232008 9 -, , 5 ,
Direct Arylation of Arene C-H Bonds by NHC-Ru(II) C atalyst.Ru
Direct arylation observed by cooperative action of NHC-Ru(II) catalyst and carbonate via proton abstraction mechanism.
ÖZDEMIR, I; DEMIR, S.; ÇETINKAYA, B.; GOURLAOUEN, C.; MASERAS, F.; BRUNEAU, C.; DIXNEUF P.H.
BP
N
Ar-Br[RuCl2(p-cymene)]2 cat., Cs2CO3
N NAr1 Ar1
Cl-N
Ar
Ar
2.2 equiv.
NMP, 120 °C
Fair to high yield, various Ar and NHC tested
Cs
J. Am. Chem. Soc. 1156 11572008 130 -, , 4 ,
31
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis and Activity of a New Ruthenium Olefin Metathesis Catalyst.Ru
New ruthenium olefin metathesis catalysts coordinated with thiazol-2-ylidene ligands along with kinetic studies arereported.VOUGIOUKALAKIS, G.C.; GRUBBS, R.H.
BP
RuCl
Cl
SNArEtO2C CO2Et1 mol% Ru Cat.
Ru Cat.
EtO2C CO2Et
C6D6, 60 °C>98%, 27 min.
O
J. Am. Chem. Soc. 2234 22452008 130 -, , 7 ,
Ruthenium-Based Redox Active Molecular Wires for Molecular ElectronicsRu
OLIVIER C.; KIM, B.; TOUCHARD, D.; RIGAUT, D.
PG
Ru
Ph2P PPh2
Ph2P PPh2
CN Ru
Ph2P PPh2
Ph2P PPh2
Ru
Ph2P PPh2
Ph2P PPh2
NCGold Gold
Au
Organometallics 509 5182008 27 -, , 4 ,
Ring-Closing Metathesis in the Synthesis of Functionalyzed NonalactonesRu
RAMIREZ-FERNANDEZ, J.; COLLADO, I. G.; HERNANDEZ-GALAN, R.
AF
OR2
R1
R4
R5
R6
R3
O
OR1
R2
R3
R4
R5
R6"Ru"
CH2Cl250 °C, 12 h
O
OR1
R2
R3 R4
R6
R5
46 - 71 %
or N N
RuClCl
Ph
PCy3
Mes Mes
"Ru":
Synlett 339 3422008 -, , 3 ,
Synthesis of Fluorinated Cyclic HydrazinesRu
DE MATTEIS, V.; VAN DELFT, F.L.; TIEBES, J.; RUTJES, F.P.J.T.
AF
NN
PhAcPh
Boc
F
Grubbs II(20 mol %)
PhMe100 °C, 2 h
64 %
NN
Ph
PhAc
BocF
Synlett 351 3542008 -, , 3 ,
32
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Catalyzed Bicyclisation of AllenynesRu
VOVARD-LE BRAY, C.; DÉRIEN, S.; DIXNEUF, P.H.; MURAKAMI, M.
AF
TsN
R1
R2
RuCl(cod)Cp*(8 mol %)
r.t., 1 - 19 h85 - 100 % conv.40 - 85 % yield
TsN+ N2CHSiMe3
Me3Si
R2
R1 R1, R2 = Me, Me; Me, Et; iPr, iPr; -(CH2)5-
Synlett 193 1962008 -, , 2 ,
Ring-Rearrangement Metathesis Synthesis of DendrochrysineRu
DOCHNAHL, M.; SCHULZ, S.R.; BLECHERT, S.
AF
NCbz
OTBS
NNs
NNs
OTBS
NCbz
91 %
I (5 mol %)
tolueneethylene atm
NMe
O
N
O(-)-trans-dendrochrysine
Ru
O
NN
Cl
Cl
Mes Mes
I:
Synlett 2599 26012007 -, , 16 ,
Synthesis of Oxepin- and Oxocin-Annulated QuinolinesRu
10 examples, yields: 78-96%.
ROTZOLL, S.; GORLS, H.; LANGER, P.
GJ
N CH3
O
N CH3
O
Ru
PCy3
PCy3
ClCl
PhCH2Cl2, -20°C, 8 h
catalyst (5 mol%)
catalyst
83%
Synthesis 45 522008 -, , 1 ,
Chiral [1,2]-Oxazine Structures.Ru
REDDY, V. K.; MIYABE, H.; YAMAUCHI, M.; TAKEMOTO, Y.
PL
I
NO Ph
I
NO Ph
NO
Ph
MesN NMes
RuPh
PCy3
Cl
Cl
benzene, 70°C, 10h
Pd(PPh3)4Et3N, MeCN80°C, 20h
79% 96%, 68% ee
IrPd
Tetrahedron 1040 10482008 64 -, , 6 ,
33
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of Thiaerythrinane by RCMRu
ABDULLAH, M. N.; ARRASATE, S.; LETE, E.; SOTOMAYOR, N.
PL
H3CO
H3CO
S
O
R
H3CO
H3CO
S
O
R
NMesMesN
Ru
PhPCy3
Cl
Cl
R = H, CH3
79-83%CH2Cl2, reflux, 12h
Tetrahedron 1323 13322008 64 -, , 7 ,
Hybrids of Azasugars by RCMRu
KUMAR, A.; RAWAL, G. K.; VANKAR, Y. D.
PL
O
O
O OCH3
Ph
O
O
O
BocN
OCH3
Ph
R2R1 R1 = H, R2 = NBocAllyl
R1 = NBocAllyl, R2 = H
2nd Gen. Grubbs' catalyst6 mol%, CH2Cl2, reflux
5 h, 85%
Mg
Tetrahedron 2379 23902008 64 -, , 10 ,
Aqueous Asymmetric Transfer Hydrogenation Ru
New modular Ru/aminoalcohol systems were used as enantioselective catalysts.
ALZA, E.; BASTERO, A.; JANSAT, S.; PERICAS, M. A.
PL
O OH
[RuC(p-cymene)]2, L*
HCO2Na/H2OOR1
NHR2
OH
R1 = Me, CPh3
R2 = Ph, 4-Ph-C6H4, 4-CF3-C3H4, 4-F-C6H4
Yield = 13-94%E.e. = 48-84%
Tetrahedron Asymm. 374 3782008 19 -, , 3 ,
Ring-Rearrangement MetathesisRu
DONNARD, M.; TSCHAMBER, T.; DESRAT, S.; HINSINGER, K.; EUSTACHE, J.
PL
O O
O
AcO
O O
O
AcO
OO
OAcH2, Pd/C
2nd generationGrubbs' catalyst
toluene, 60°C, 3h
86%
Tetrahedron Lett. 1192 11952008 48 -, , 7 ,
34
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Ru-Catalyzed Silylation of Silanols with Vinylsilanes Ru
MARCINIEC, B.; PAWLUC, P.; HRECZYCHO, G.; MACINA, A.; MADALSKA, M.
PL
O HR'3Si SiR3O SiR3R'3Si
R, R' = alkyl, aryl, siloxy, alkoxy
+RuHCl(CO)(PCy3)2
toluene, 110-120°C[silanol]/[catalyst] = 1:2 X 10-2 mol 49-99%
Tetrahedron Lett. 1310 13132008 48 -, , 8 ,
Efficient 2-Iminomethylpyridine/Cobalt-Based Alkyne [2+2+2] Cycloaddition Co
Additive is enabling the use of unactivated, simple internal alkynes as the monoyne substrate.
GOSWAMI, A.; ITO, T.; OKAMOTO, S.
AF
H
H
EtO2C
EtO2C
H
Ph
EtO2C
EtO2C Ph
+
CoCl2.6H2O / L (5 mol %)AgOTf (10 mol %)
Zn powder (10 mol %)THF, r.t., 0.5 h
97 % (92 % isolated)1.3 equiv
iPr
iPr
N NL:
Ag
Adv. Synth. Catal. 2368 23742007 349 -, , 14-1
,
Cobalt-Catalyzed Reductive Mannich Reactions with N-Tosyl AldiminesCo
PRIETO, O.; LAM, H. W.
AE
O
N
O
H Ar
NTs
O
N
O
Ar
NHTs
Et2Zn 2 eq.Co(acac)2.2H2O (5 mol%)
+
9 examples, yield>78% (anti-isomer)
Org. Biomol. Chem. 55 572008 6 -, , 1 ,
Synthesis of Dicobalt Hexacarbonyl Complexes of 5-Alkynyl-2’-DeoxyuridinesCo
SERGEANT, C. D.; OTT, I.; SNIADY, A.; MENENI, S.; GUST, R.; RHEINGOLD, A. L.; DEMBINSKI, R.
AE
OHO
HO
HN
O
O R
OHO
HO
HN
O
O R(OC)3Co
Co(CO)3
Co2(CO)8
THF8 examples, yield : 77-93%
Org. Biomol. Chem. 73 802008 6 -, , 1 ,
35
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
An Extension of the Wittig Reaction: Attack of P Ylides at Acyl Groups in Co Compl.Co
WANG, Q.; SUN, H.; FANG, S.; LIU, M.; HARMS, K.; LI, X.
AN
OCoL3H
O
R + H2C PPh3
THF
- Ph3P=O OCoR
L
LL
R =
OMe
L = P(CH3)3
Organometallics 6805 68112007 26 -, , 27 ,
Cyclometalation Reactions Involving C-Cl Bond Activation of ortho-Chlorinated Substrateswith Imine as Anchoring Groups by Cobalt Complexes
Co
CHEN, Y.; SUN, H.; FLÖRKE, U.; LI, X.
AN
ClN
H R
Cl
+ CoMe(PMe3)4- 2 PMe3
Cl
NH
R
Co
PMe3
PMe3
Cl
Me
Organometallics 270 2752008 27 -, , 2 ,
1,4 asymmetric AlkylationCo
HAYASHI, Y.; YAMAGUCHI, H.; TOYOSHIMA, M.; NASU, S.; OCHIAI, K.;SHOJI, M.
PJF
Co Co
O OMOM
H Ph
Co Co(CO)3
OH OMOM
Me Ph
Me3ZnLi
Toluene, -100 °C
90%, dr 6:1 ->20:1
(CO)3
Organometallics 163 1652008 27 -, , 2 ,
Asymmetric Nicholas ReactionCo
LJUNGDAHL, N.; PARERA PERA, N.; ANDERSSON, K.H.O.; KANN, N.
AF
HO
O
1. Co2(CO)8 CH2Cl2, r.t.
2. L* (2 equiv) toluene 50 °C
HO
O(*L)2(OC)4Co2
1. BF3.OEt2, 4 CH2Cl2 - 30 °C to r.t.
2. CAN THF - H2O (9 : 1), - 10 °C
O
O*
35 %, 74 % ee
OO
P NL*:
OSiMe34:
Synlett 394 3982008 -, , 3 ,
36
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of Vinyl-Substituted 1,4-Diphenylcyclohexa-1,3-dienesCo
[2+2+2]-Cycloaddition of two alkynes and a double bond of an 1,3-diene.
HILT, G.; HESS, W.; HARMS, K.
GJ
CH3
Ph
Ph
PhCH
3
CoBr2(PPh3)2 (5 mol%)
Zn (10 mol%)+
2 equivCH2Cl2, rt, 15 h
ZnI2 (10 mol%)51%
Zn
Synthesis 75 782008 -, , 1 ,
Asymmetric 1,3-Dipolar Cycloaddition of α,βα,βα,βα,β-Unsaturated Aldehydes and NitronesRh
DANIEL CARMONA, D.; LAMATA, M.P.; VIGURI, F.; RODRIGUEZ, R.; FISCHER, T.; LAHOZ, F.J.; DOBRINOVITCH, I.T.;ORO, L.A.
AF
O
MeN
O+
NO
MeMe
Me
OHC
- 25 °C, 72 h 96.5 %, 92 % ee
IrPh2P
PPh2Me
OMe
Me
2+
"Ir" (10 mol %)
4A MSCH2Cl2
"Ir" :Ir
Adv. Synth. Catal. 1751 17582007 349 -, , 10 ,
Carbonylative Addition of Arylboronic Acids to Term inal AlkynesRh
Optimization of the reaction conditions.
DHEUR, J.; SAUTHIER, M.; CASTANET, Y.; MORTREUX, A.
AF
Ar B(OH)2 + R H
O
ArH
RH
[Rh(cod)Cl]2(0.5 mol %)
CO (5 bar)MeOH
80 °C, 18 h 27 - 69 %
Ar = Ph, p-CH3-C6H4, p-CH3O-C6H4, p-Cl-C6H4, m-Cl-C6H4, p-F-C6H4R = C4H9, C5H11
B
Adv. Synth. Catal. 2499 25062007 349 -, , 16 ,
Spirobitetraline Phosphoramidite for Asymmetric HydrogenationRh
Synthesis of the ligands reported.
HUO, X.-H.; XIE, J.-H.; WANG, Q.-S.; ZHOU, Q.-L.
AF
92 - 99.3 % ee
[Rh(cod)2]BF4 / (S)-3a (1 mol %)
CH2Cl2 / toluene(1/4, v/v)
r.t., 2 - 3 h100 %
+ H2
10 atmAr
CO2Me
NHAc Ar
CO2Me
NHAc
O
OP NMe2
(S)-3a:
Adv. Synth. Catal. 2477 24842007 349 -, , 16 ,
37
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
N-Heterocyclic Carbene Substituted Phosphines and Phosphites in HydrogenationRh
Several carbene complexes prepared, characterized, and tested.
HERRMANN, W.A.; FREY, G.D.; HERDTWECK, E.; STEINBECK, M.
AF
+ H2"Rh"
61 %toluene80 °C, 3 h30 bar
Cy
Cy
RhPPh3
PPh3
Cl
"Rh"
Adv. Synth. Catal. 1677 16912007 349 -, , 10 ,
Josiphos Ligands with an Imidazolium Tag in Asymmetric Hydrogenation Rh
Efficent recycling.
FENG, X.; PUGIN, B.; KÜSTER, E.; SEDELMEIER, G.; BLASER, H.-U.
AF
14 - 100 %30 - 99 % ee
according to the solvent
CO2Me
R
R = NHAc, CH2CO2Me
[Rh(NBD)2 ]BF4 + P2*(0.5 mol %)
P2*:
TBME / [BIM][BF4]or other solvents
CO2Me
R+ H2
1 barFeR2P
PCy2
H HN N
O
N +
-N(SO2CH3)2R = Ph, 3,5-(CF3)2C6H3
Fe
Adv. Synth. Catal. 1803 18072007 349 -, , 10 ,
Cationic Chiral Dirhodium Carboxamidates are Activated Lewis AcidsRh
WANG, Y.; WOLF, J.; ZAVALIJ, P.; DOYLE, M. P.
AF
NPh O-
Ar
+
+Me CHO N
ON
OPh
Ar
Ph
ArCHOMe
CHO
Me+
"Rh2"(1 - 5 mol %)
CH2Cl24 A MS
2,6-di-tert-butylpyridine (10 mol %)
Rh
O
Rh
COO
+SbF6-"Rh2":
16:84 to 90:10
21 - 94 % ee 28 - 71 % ee
Angew. Chem. Int. Ed. 1439 14422008 47 -, , 8 ,
Rearrangement of Aryl Bis(alkynyl) Carbinols to 3-Alkynyl-1-indanonesRh
SHINTANI, R.; TAKATSU, K.; KATOH, T.; NISHIMURA, T.; HAYASHI, T.
AF
63 - 87 %
OH
Si
Si
R[Rh(OH)(cod)]2 (4 mol %)
BINAP (4.4 mol %)
dioxane50 °C
O
SiSi
RR = H, 2-Me, 4-Me, 4-OMe, 4-F, 4-ClSi = SiMe2(tBu), SiEt3, Si(nPr)3,
Angew. Chem. Int. Ed. 1447 14492008 47 -, , 8 ,
38
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
[2+2+2] Cycloaddition of 1,6-Enynes Rh
TANAKA, K.; OTAKE, Y.; SAGAE, H.; NOGUCHI, K.; HIRANO, M.
AF
MeTsN
Me
O
CO2EtMe
[Rh(cod)2][BF4] / L*(10 mol %)
CH2Cl280 °C, 15 h
+
1.1 equiv
OTsN
MeCO2EtMe
Me10 - 99 %
91 - 96 % eeL* = binap, tol-binap, xyl-binap, segphos, H8-binap
Angew. Chem. Int. Ed. 1312 13162008 47 -, , 9 ,
Carbene Ligand Bearing a Phosphorus YlideRh
Applied in the palladium catalyzed arylation of morpholine.
NAKAFUJI, S.-Y.; KOBAYASHI, J.; KAWASHIMA, T.
AF
N
PPh3+
H
Me
I-
N
PPh3+
H
Me
BPh4-NaBPh4
1) MesLi2) [Rh(cod)Cl]2
- 78 °C N
PPh3
Rh
MeCl N
PPh3
Rh
Me
CO
CO
Cl
CO
r.t.
Pd
Angew. Chem. Int. Ed. 1141 11442008 47 -, , 6 ,
A Chiral Stannate as an “ansa” ππππ-Arene Ligand in Rhodium ChemistryRh
KILIAN, M.; WZDEPOHL, H.; GADE, L. H.
MVI
Si
Me
Si
Me2SiSiMe2
N
N
NSn
Rh
iPr3P
Me2
Sn
Dalton Trans 582 5842008 -, , 5 ,
Enones Asymmetric AlkynylationRh
NISHIMURA, T.; GUO, X.-X.; UCHIYAMA, N.; KATOH, T.; HAYASHI, T..
PJF
O
R1
R2 Si-iPr3
O
R1
R2
Si-iPr3
Rh(µ-OAc))(C2H4)2]2(R)-DTBM-segphos
dioxane, 40 °C+
54-99%88-97% ee
J. Am. Chem. Soc. 1576 15772008 130 -, , 5 ,
39
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Alkyne Hydrothiolation with Alkanethiols and Wilkin son’s CatalystRh
SHOAI, S.; BICHLER, P.; KANG, P.; BUCKLEY, H.; LOVE, J. A.
PB
R' R'SR
RSH +3 mol% ClRh(PPh3)
DCE 15 examples44-94%
Organometallics 5778 57812007 26 -, , 24 ,
[( tBu2PCH2SiMe2)2N]Rh I? Rapidly Reversible H-C(sp3) and H-C(sp2) Bond Cleavage byRhodium(I)
Rh
VERAT, A.Y.; PINK, M.; FAN, H.; TOMASZEWSKI, J.; CAULTON, K.G.
AN
N Rh
Me2Si PtBu2
Me2Si PtBu2
RhNH
PtBu2
PtBu2
Organometallics 166 1682008 27 -, , 2 ,
Rh(I) Complexes with Hemilabile N-Heterocyclic Carbenes: Efficient Alkyne HydrosilylationCatalysts
Rh
JIMENEZ, M.V.; PEREZ-TORRENTE, J.J.; BARTOLOME, M.I.; GIERZ, V.; LAHOZ, F.J.; ORO, L.A.
AN
NN
H
RNH n
++
2 Cl_
[Rh(µ-Cl)(cod)]2
2 KOH
N
N(COD)Rh
R
NnCl
R = Me, n = 2, 3R = tBu, n = 2, 3R = Mes, n = 3
Organometallics 224 2342008 27 -, , 2 ,
Rhodium Catalyst for Alkyne HydrosilylationRh
JIMENEZ, M. V.; PEREZ-TORENTE, J. J.; BARTOLOME, M. I. GIERZ V.; LAHOZ, F. J.; ORO, L. A.
PJF
RhCl
N
NR
N
R1
H-SiMe2Ph
Si
Organometallics 224 2342008 27 -, , 2 ,
40
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Asymmetric Direct Aldol ReactionRh
INOUE, H.; KIKUCHI, M.; ITO, J.-I.; NISHIYAMA, H.
AF
O
+ H
O
R
O OH
R
"1b" (5 mol %)AgOTf (5 mol %)
toluene60 °C, 72 h
R = p-F, p-Br, p-CO2Me, p-CF3, o-NO242 - 75 %
syn/anti = 10:90 to 27:73ee syn = - to 16 % eeee anti = 66 to 86 % ee
NO
ON
RhOAc
OH2OAc
iPr
iPr
1b:
Tetrahedron 493 4992008 64 -, , 3 ,
Enantioselective [2+2+2] Cycloaddition of Diynes with Unfunctionalized AlkenesRh
Styrene also used.
SHIBATA, T.; KAWACHI, A.; OGAWA, M.; KUWATA, Y.; TSUCHIKAMA, K.; ENDO, K.
AF
RZ
CO2Me+
[Rh(cod)2]BF4 (10 mol %)Difluorophos (10 mol %)
CH2Cl2r.t., 1 - 4 h51 - 93 %
Z
R
CO2Me91 - 99 % ee2 equiv
PPh2
PPh2O
O
O
O
F
F
FF
Difluorophos:
Tetrahedron 12853 128592007 63 -, , 52 ,
Reductive Aldol Coupling and Subsequent DehydroxylationRh
HASHIMOTO, T.; SHIOMI, T.; ITO, J.-I.; NISHIYAMA, H.
AF
NO
ON
RhOAc
OH2OAc
iPr
iPr
"Rh" :X
CHO
+Y
CO2iPr
"Rh" (1 mol %)MePh2SiH
toluene50 °C
than H3O+ or F-
Et3SiH
CH3CO2Hr.t. to 50 °C
X
CO2iPr
Y
X = MeO, Me, NMe2Y = H, MeO, Me, NMe2, Cl, CF3
63 - 92 %88 - 93 % ee
Tetrahedron 12883 128872007 63 -, , 52 ,
αααα-Fluoroalkylation of α,βα,βα,βα,β-Unsaturated KetonesRh
Scope of the process and mechanism presented.
SATO, K.; ISHIDA, Y.; MURATA, E.; OIDA, Y.; MORI, Y.; OKAWA, M.; IWASE, K.; TARUI, A.; OMOTE, M.; KUMADAKI,I.; ANDO, A.
AF
Rf XO
R R'
O
RRf
R'+
Et2ZnRhCl(PPh3)3
THF0 °C, 0. 5 - 5 h
Rf = CF3, C3F7, C10F21, EtCO2CF2,
X = I, Br, Cl
41 - 77 %
Tetrahedron 12735 127392007 63 -, , 51 ,
41
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Hetero-Diels–Alder ReactionRh
Applied to the asymmetric syntheses of diarylheptanoid natural products.
WASHIO, T.; YAMAGUCHI, R.; ABE, T.; NAMBU, H.; ANADA, M.; HASHIMOTO, S.
AF
R1
OSiEt3
O
H
R2
O
R1
R2
O1. Rh2(R-BPTPI)4
(1 mol %)CH2Cl2
2. TBAF, THF23 °C, 0.5 h
+
N
O
ONH
ORh Rh
Rh2(R-BPTPI)4R1 = OMe, OBn, R2 = H, OTBS, OMs 15 - 87 %87 - 93 % ee
Tetrahedron 12037 120462007 63 -, , 48 ,
Cyclization–Cycloaddition Cascade of αααα-Diazo DihydroindolinonesRh
Other examples give.
ENGLAND, D.B.; EAGAN, J.M.; MEREY, G.; ANAC, O.; PADWA, A.
AF
N
N
ON2
CO2Et
OMe
O
+ A B N
N
Me
O
BA
O
EtO2C
O
Rh2(OAc)4 (1.6 mol %)
75 - 85 %
benzenereflux, 1 h
A=B:O
O
O
O
OMe
CO2Me
H
O
Tetrahedron 988 10012008 64 -, , 6 ,
Planar-chiral Metacyclophanes Enantioselective Synthesis via CyclotrimerizationsRh
Several other examples given.
TANAKA, K.; SAGAE, H.; TOYODA, K.; HIRANO, M.
AF
MeO
O
O
Z
O OMe
[Rh(cod)2][BF4] (5 mol %)(R)-H8-BINAP
CH2Cl2r.t., 16 h(0.01 M)
MeO
Me
OO
O
ZO
(CH2)n n = 1 - 5, 98 - 91 % ee
Tetrahedron 831 8462008 64 -, , 5 ,
Asymmetric HydrogenationRh
Acceleration induced by self-assembly of the ligands around the metal in propylene carbonate.
SCHÄFFNER, B.; HOLTZ, J.; VEREVKIN, S.P.; BÖRNER, A.
GP
R R'
CO2Me
R R'
CO2Me
PNH O[Rh(cod)2]BF4, 2L*, H2
CH2Cl2 ou propylene carbonate
*
ee%: 55-94%
L*
Tetrahedron Lett. 768 7712008 49 -, , 5 ,
42
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Prototropic Rearrangements in Cycloheptatrienyl PCP Pincer Iridium ComplexesIr
The two hydrides have moved into the ligand backbone
WINTER, A. M.; EICHELE, K.; MACK, H.-G.; KASKA, W. C.; MAYER, H. A.
MVI
PtBu2
Ir
PtBu2
COH
H
PtBu2
Ir
PtBu2
CO
H
H
H rearrangement
Dalton Trans 537 5322008 -, , 4 ,
C-C Catalytic CouplingIr
BOWER, J. F.; SKUCAS, E.; PATMAN, R. L.; KRISCHE, M. J.
PJF
Me
Me
OH
R1
OH
R1
O
R1H
+[Ir(cod)(BIPHEP)]BARF
CsCO3
or + iPrOH70-92%
J. Am. Chem. Soc. 15134 151352007 129 -, , 49 ,
Meta Arene HalogenationIr
MURPHY, J. M.; LIAO, X.; HARTWIG, J. F.
PJF
R
R1
BO
OO
OB
R
R1
X+
1) [Ir(cod)(OMe)2]2dtbpy
2) CuX2
X = Cl, Br46-77%
J. Am. Chem. Soc. 15434 154352007 129 -, , 50 ,
New Thiazole-Based Iridium Catalysts and Their ApplicationsIr
CHERUKU, P.; PAPTCHIKHINE, A.; ALI, M.; NEUDÖRFL, J.-M.; ANDERSSON, P. G.
AE
R
Ar
R
Ar *
cat. [Ir] (0.5-1 mol%)
CH2Cl2, RT, 50 bar H2 R
S
NPh
Ph2P
Ir
BArF
R = Bn, Me, Allyl
cat. [Ir] :
11 examples
Org. Biomol. Chem. 366 3732008 6 -, , 2 ,
43
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Asymmetric Hydrogenation of QuinolinesIr
R = Me, Ph; R’ = H, Me, OMe. Variation of the iridium complexes.
DEPORT, C.; BUCHOTTE, M.; ABECASSIS, K.; TADAOKA, H.; AYAD, T.; OHSHIMA, T.; GENET, J.-P.; MASHIMA, K.;RATOVELOMANANA-VIDAL, V.
AF
N
R'
R
[Ir-(S)-SYNPHOS]
+ H2
50 barTHF
I2
30 °C, 24 h70 - 100 % conv
NH
R'
R
56 - 92 % ee
O
OO
O
PPh2
PPh2(S)-SYNPHOS:
Synlett 2743 27472007 -, , 17 ,
Direct Oxidative Esterification of Adehydes with AlcoholsIr
Several examples given.
KIYOOKA, S.-I.; WADA, Y.; UENO, M.; YOKOYAMA, T.; YOKOYAMA, R.
AF
PhCHO + OH Ph O
O
65 %Ph O
O
13 %
[Ir(cod)]2 (5 mol %)K2CO3 (10 mol %)
toluener.t., 12 h
+
Tetrahedron 12695 127012007 63 -, , 51 ,
N-alkylation of Amines with AlcoholsIr
Alkylation of primary and secondary amines with primary and secondary alcohols.
FUJITA, K.-I.; ENOKI, Y.; YAMAGUCHI, R.
AF
NHR2
R1
+ OHR4
R3[IrCp*Cl]2 (1 - 5 mol %)
NaHCO3
toluene110 °C, 17 h
R2 N R4R1
R3
44 - 96 %
Tetrahedron 1943 19542008 64 -, , 8 ,
Consecutive and Enantioselective [2+2+2] Cycloadditions Ir
Several examples given.
SHIBATA, T.; YOSHIDA, S.; ARAI, Y.; OTSUKA, M.; ENDO, K.
AF
[IrCl(cod)]2 (10 mol %)xylylBINAP (20 mol %)
xylener.t., 15 h
81 %, 97 % ee
PhO
O
O
OPh
O
O
O
O
PhPh
Tetrahedron 821 8302008 64 -, , 5 ,
44
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Homocoupling of 4-Chloroquinolones Leading to Symmetrical BisquinolonesNi
R1 = Me, R2 = H, OMe, R3 =H, OMe, R4 = H, OMe, R1-R2 = (CH2)2
HASHIM, J.; KAPPE, C.O.
AF
N
R4
R3
R2 R1O
Cl
N
R4
R3
R2 R1O
N
R4
R3R2R1
ONiCl2(PPh3)2 (25 mol %)DPEphos (25 mol %)
Zn dust ( 1.8 equiv)KI (0.8 mL)dry dioxane
130 °C (MW), 30 min
OPPh2 PPh2
DPEphos
71 - 92 %
Adv. Synth. Catal. 2353 23602007 349 -, , 14-1
,
A Bench-Stable Homodinuclear Ni2-Schiff Complex for Asymmetric CatalysisNi
Both Ni centers are important in this reaction
CHEN, Z.; MORIMOTO, H.; MATSUNAGA, S.; SHIBASAKI, M.
MVI
N
R1
Boc
R2CO2tBu
NO2
NH
R1 CO2tBu
R2 NO2
Boc
Ni2
O
O
N
O
O
NNi
Ni
+cat. Ni2 (1-10 mol%)
96-97% yielddr up to 97:3ee 91-99%
J. Am. Chem. Soc. 2170 21712008 130 -, , 7 ,
Amination of Aryl TosylatesNi
The actual catalyst is a Ni(II) species.
GAO, C.-Y.; YANG, L.-M.
CC
OTs
R
NRR'
R
+ HNRR'
Ni(PPh3)2(1-naphtyl)Cl (5%)IPr.HCl (5%)
dioxane, t-BuONa, 110°C
36 examples24-92%
J. Org. Chem. 1624 16272008 73 -, , 4 ,
Silane-Promoted Ni-Catalyzed AminationNi
MANOLIKAKES, G.; GAVRYUSHIN, A.; KNOCHEL, P.
CC
Cl
R
NRR'
R
NN
Br Br
Br Br
+ HNRR'(N) (N)
Ni(acac)2 (0.5%)L (1%), DME (2%)
t-BuONa, PMHStoulene, reflux 32 examples
53-97%
PHMS= polymethylhydrosiloxane
L=
Si
J. Org. Chem. 1429 14342008 73 -, , 4 ,
45
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Nickel(II) Complexes Supported by Pyridine-Functionalized N-Heterocyclic CarbeneNi
Ni(II) complex / PPh3 / K3PO4 catalyses the Suzuki coupling reaction of arylbromides and chlorides
XI, Z.; ZHANG, X.; CHEN, W.; FU, S.; WANG, D.
PB
N
N
N
N
NNNi
N
N
N
N
NNNi
2+2+
Organometallics 6636 66422007 26 -, , 26 ,
Modular P-N Ligands Derived from 3-Amino-1,2-diolsPd
5 ligands prepared.
POPA, D.; PUIGJANER, C.; GOMEZ, M.; BENET-BUCHHOLZ, J.; VIDAL-FERRAN, A.; PERICAS, M.A.
AF
R R
R1
R = Ph, Me, iPr, 4-Cl-C6H4
R1= H, Ph
OAc 13a (2.5 mol %)
BSA, KOAcCH2(CO2Me)2
solvent-10 - 130 °C
1.5 - 96 h
R R
R1 CH2(CO2Me)2
N
O
Ph
OMePh2PPd
+PF6-
13a:
42 - > 99 % conv.35 - 98 % ee
Adv. Synth. Catal. 2265 22782007 349 -, , 14-1
,
N-Heterocyclic Carbene Complexes in Large- Scale Cross-Coupling ReactionsPd
Precatalyst provids efficient catalyst for Buchwald-Hartwig and α-ketone arylation reactions.MARION, N.; DE FRÉMONT, P.; PUIJK, I.M.; ECARNOT, E.C.; AMOROSO, D.; BELL, A.; NOLAN, S.P.
AF
OPd
OO O
N NR R
H Cl
+
technical grade1,4-dioxane
100 °C, 44 hin air
PdCl
O ON
N
R
R
R=
93 %
14 g prepared
Adv. Synth. Catal. 2380 23842007 349 -, , 14-1
,
Accelerated Very Low Ligandless Catalyst in Heck ReactionPd
A combination of microwave and untrasound accelerates the reaction vs oil bath heating.
PALMISANO, G.; BONRATH, W.; BOFFA, L.; GARELLA, D.; BARGE, A.; CRAVOTTO, G.
AF
Pd(OAc)2(0.01 - 0.05 mol %)
DMA, K2CO3/TBABMW/US
R X +
R
R
R= OCH3, COCH3, NO2X= I or Br, Br or Cl, Cl
+
1:5 to 1:1343 - 100 % conv.
Adv. Synth. Catal. 2338 23442007 349 -, , 14-1
,
46
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Intermolecular Coupling of Organic Halides with Alkynes and AlkenesPd
SHIBATA, K.; SATOH, T.; MIURA, M.
AF
Pd(OAc)2 (5 mol %)LiCl (0.5 or 0.7 equiv)
base (1 or 2 equiv)DMF / H2O
0.5 - 4 hX = I, Br base = Ag2CO3, Cs2CO3, NaHCO3
1 equiv 4 equiv 1 equiv
PhPh
CO2tBu CO2tBu
16 - 70 % 12 - 58 %
+X Ph
PhCO2tBu+ +
Adv. Synth. Catal. 2317 23252007 349 -, , 14-1
,
Aromatic Amination in Medicinal ChemistryPd
Several examples of two fold amination of 2,4- and 2,5-dihalogenated aromatic compounds reported.
TASLER, S.; MIES, J.; LANG, M.
AF
NNNN
Cl
S
NH2N
S
NHN
NNNN
+
1.0 : 1.2
Pd2dba3 (4 mol %)Xantphos (12 mol %)
K3PO4 (1.4 equivs)dioxane
100 °C, 24 h73 %
Adv. Synth. Catal. 2286 23002007 349 -, , 14-1
,
[5+2] Annulation Leading to 1-Benzoxepines from 2-Aroylmethoxyarylboronic AcidsPd
Optimization of the process and more than 13 examples given.
LIU, G.; LU, X.
AF
R2 B(OH)2
OR1
O
R
CO2Me O
R3
RCO2Me
R1
OH
[Pd(dppp)(H2O]2+(OTf-)2(5 mol %)
Amberlite IRA-400 OH(1.5 equiv)
DME, 60 °C
+
41 - 94 %
Adv. Synth. Catal. 2247 22522007 349 -, , 14-1
,
Double Sonogashira Coupling of Aryl Chlorides with 2-Methyl-3-butyn-2-olPd
Unsymmetrical coupling also possible (20 - 30 % yield).
YI, C.; HUA, R.; ZENG, H.; HUANG, Q.
AF
R = 4-Me, 4-CH=CH2, 4-C(CH3)Me, 3-CO2Mealso 2-chlorothiophene and 1-chloro-naphtalene
77- 95 %
Cl
R +OH
Me
Me
PdCl2(PCy3)2 (5 mol %)
Cs2CO3piperidine
DMSO120 °C, 12 h
R R
Adv. Synth. Catal. 1738 17422007 349 -, , 10 ,
47
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Enantioselective 1,4-Addition of Arylboronic Acids to ββββ-ArylenonesPd
NISHIKATA, T.; YAMAMOTO, Y.; MIYAURA, N.
AF
Ar
OO
+B(OH)2
FG[Pd(S,S-chiraphos)(PhCN)2][SbF6]2
(1 mol %)
5 mmol 6 mmol
AgBF4 or AgSbF6(0.01 or 0.05 equiv)acetone/water (10:1)
0 - 25 °C, 21 h10 - 99 %
92 - 99 % ee
Ar
Ar'R
O
Ar = Ph, 4-MeOC6H4, 2-naphtylR = Me, nC4H9, 2-C3H7, Cy, Ph, 4-MeOC6H4, 4-NO2C6H4FG = 3-Cl, 3-MeO, 4-MeO, 4-Me, 4-COMe, 4-MeS, 3,4-O2CH2
Adv. Synth. Catal. 1759 17642007 349 -, , 10 ,
Enantioselective Carbonyl-Ene Reactions of Arylglyoxals Pd
21 recyclings in an ionic liquid. With dienes, only one carbonyl ene reaction occurred.
LUO, H.-K.; KHIM, L.B.; SCHUMANN, H.; LIM, C.; JIE, T.X.; YANG, H.-Y.
AF
R1 H
R2H
OAr
O R1
R2
OHAr
O
*
[Pd(R-BINAP)][SbF6]2(5 mol %)
5 ex 10 ex
CH2Cl2r.t., 0.5 - 3 h
17 - 59 %73.6 - 93.8 % ee
+
Adv. Synth. Catal. 1781 17952007 349 -, , 10 ,
New ONN-Pincer Complexes Applied in CatalysisPd
Synthesis of ligands, use in Heck reaction, Suzuki coupling, and hydrosilylation reported.
DEBONO, N.; IGLESIAS, M.; SANCHEZ, F.
AF
CO2EtCO2Et
+ H2
4 atm 40 °C, 7 h96 %
80 % ee
"Au" (0.1 mol %)
CO2EtCO2Et
N
NO Au
Cl
CONHtBu
"Au" :Au
Adv. Synth. Catal. 2470 24762007 349 -, , 16 ,
Direct Arylation of Thiophenes Pd
BATTACE, A.; LEMHADRI, M.; ZAIR, T.; DOUCET, H.; SANTELLI, M.
AF
SH R1
R2
ArBr +SAr R1
R2
R1 = 4-tBuC6H4, R2 =HR1 = 4-CF3C6H4, R2 = HR1 = COCH3, R2 = CH313 ex
1/2 [PdCl(C3H5)]2(1 - 0.01 mol %)
L (1 - 0.01 mol %)
AcONaDMAc
150 °C, 20 h 37 - 87 % isolated
Ph2P
Ph2P PPh2
PPh2
L:
Adv. Synth. Catal. 2507 25162007 349 -, , 16 ,
48
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Discrimination between Molecular and Colloidal CatalystsPd
Other diphosphite ligands and substrates used. Comparison with colloïdal palladium based catalysts.
FAVIER, I.; GOMEZ, M.; MULLER G.; AXET, M. R.; CASTILLON, S.; CLAVER, C.; JANSAT, S.; CHAUDRET, B.;PHILIPPOT, K.
AF
OAc
+ CH2(CO2Me)2
[PdCl(C3H5)]2
BSA, KOAcCH2Cl2, r.t., 0.25 h
48 %
OAc(0.5 mol %)
88 % ee
L*O O
P PO
O
O
O
L*:
OO
t-But-Bu
t-Bu t-Bu
O O =
Adv. Synth. Catal. 2459 24692007 349 -, , 16 ,
On the Aromaticity of Metalated Expanded PorphyrinsPd
TANAKA, Y.; SAITO, S.; MORI, S.; ARATANI, N.; SHINOKUBO, H.; SHIBATA, N.; HIGUCHI, Y.; YOON, Z. S.; KIM, K. S.;NOH, S. B.; PARK, J. K.; KIM, D.; OSUKA, A.
CY
The palladation of [36]octaporphyrin provided Pd2 complexes which exhibit Möbius aromaticand Hückel antiaromatic characters.
Angew. Chem. Int. Ed. 681 6842008 47 -, , 4 ,
Pd-Catalysed Stereospecific Synthesis of 4-Alkoxy-5-hydroxy-2-pentenoatesPd
YU, X.-Q.; YOSHIMURA, F.; ITO, F.; SASAKI, M.; HIRAI, A.; TANINO, K.; MIYASHITA, M.
CY
BnO CO2EtO
BnO CO2EtOH
O
Pd(PPh3)4 (10 mol%), (PhO)3B (1.5 equiv),allyl alcohol (4.5 equiv), THF, 0 ºC
86%
dr > 99:121 examples
Angew. Chem. Int. Ed. 750 7542008 47 -, , 4 ,
A Domino Amination/Heck for the Synthesis of 3-Substituted IndolesPd
JENSEN, T.; PEDERSEN, H.; BANG-ANDERSEN, B.; MADSEN, R.; JORGENSEN, M.
CY
Br
I NH
Pd2(dba)3 (1.25 mol%), dppf (5 mol%)NaOtBu (2.5 equiv), toluene, 140 ºC, 2.5 h
H2N
85%
(1 equiv)
Angew. Chem. Int. Ed. 888 8902008 47 -, , 5 ,
49
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Octahedral Coordination Compounds of the Group 10 Transition MetalsPd
KIRCHMANN, M.; EICHELE, K.; SCHAPPACHER, F. M.; PÖTTGEN, R.; WESEMANN, L.
CY
6 [Na2SnB11H11]K2PdCl6, H2O, THF, nBu3NHCl (2 equiv)
[nBu3NH]2K2Na4 PdSnSn Sn
Sn
Sn
Sn
Sn = SnB11H11
8-NiPtSn
Angew. Chem. Int. Ed. 963 9662008 47 -, , 5 ,
Asymmetric Allylic EtherificationPd
LAM, F. L.; AU-YEUNG, T. T.-L.; KWONG, F. Y.; ZHOU, Z.; WONG, K. Y.; CHAN, A. S. C.
CY
Ph Ph
OAc
Ph OH
[Pd(allyl)Cl]2 (2 mol%), L (4 mol%)CsCO3 (3 equiv), toluene, room temp., 2-2.5 h
Ph Ph
O
Ph
+ Fe
SCy
L = N PPh2
Angew. Chem. Int. Ed. 1280 12832008 47 -, , 7 ,
Cross-Coupling of Aryl C–H Bonds with Aryl Boronic AcidsPd
YANG, S.-D.; SUN, C.-L.; FANG, Z.; LI, B.-J.; LI, Y.-Z.; SHI, Z.-J.
CY
NB(OH)2
Pd(OAc)2 (5 mol%), O2 (1 atm), AcOH, room temp., 10 h
(1.5 equiv)
+87% N
Angew. Chem. Int. Ed. 1473 14762008 47 -, , 8 ,
A Three Component Synthesis of PromazinePd
DAHL, T.; TORNOE, C. W.; BANG-ANDERSEN, B.; NIELSEN, P.; JORGENSEN, M.
CY
N
SSH
Br
I
BrRNH2+ +
Pd2(dba)3 (2.5 mol%), dppf (10mol%)NaOtBu (4 equiv), toluenemicrowave or conventional heating
R21-92%
18 examples
Three Ar–X (X = N, S) bondsformed in a single operation
Angew. Chem. Int. Ed. 1726 17282008 47 -, , 9 ,
50
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Asymmetric Allylic Alkylation of Acyclic AmidesPd
ZHANG, K.; PENG, Q.; HOU, X.-L.; WU, Y.-D.
CY
FeL = N
O
PO
NEt2
HONPh2
PhOO
OAcNPh2
O
PhO
+
(2 equiv)
[Pd(allyl)Cl]2 (1 mol%), L (2 mol%)LHMDS (1 equiv), LiCl (1 equiv),THF, room temp.
99%
ee = 93%
Angew. Chem. Int. Ed. 1741 17442008 47 -, , 9 ,
Linear 1-(Methanesulfonylphenyl or Benzenesulfonamido)-2-(pyridyl)acetylene Pd
The cyclooxygenase inhibitory activities of ecetylene derivatives were studied.
CHOWDHURY, M. A.; DONG, Y.; CHEN, Q.-H.; ABDELLATIF, K. R. A.; KNAUS, E. E.
PL
H
MeS
N
Br
+ het
MeO2S
1) Pd(PPh3)2Cl2, NEt3, THF, CuI, 90°C, 3-5h
2) 1,4-dioxane, aqueous Oxone25°C, 4-5h
Cu
Bioorg. Med. Chem. 1948 19562008 16 -, , 4 ,
Intramolecular Pd(II)-Catalyzed Oxypalladation: Mechanistic StudyPd
Results presented suggest a syn Pd complex, syn oxypalladation and syn elimination.
UENISHI, J.; VIKHE, Y. S.; KAWAI, N.
PG
OH
R
OH
n
[PdCl2(MeCN)2] cat.
THF
O
R
HH
n
OH
R
OH
n
[PdCl2(MeCN)2] cat.
THF
O
R
HH
n
Chem. Asian J. 473 4842008 2 -, , 3 ,
A Stable Zerovalent Palladium ChainPd
The Pd(0)4 chain is stabilized by nonactivated olefins
TATSUMI, Y.; MURAHASHI, T.; OKASA, M.; OGAOSHI, S.; KUROSAWA, H.
BJL
Pd Pd Pd PdN N
2+2 Cp2Co
2 Cp2Fe2+Pd Pd Pd PdN N
Chem. Commun. 477 4792008 -, , 4 ,
51
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Cross couplings of Unactivated Alkyl and Aryl HalidesPd
C. VALENTE, S. BAGLIONE, D. CANDITO, C. J. O'BRIEN, M. G. ORGAN
BJL
R1
Br + R2
9-BBNPd (cat)
K3PO4.H2O
rt
R1
R2 Pd (cat):Cl Pd Cl
N
Cl
NN
58-98%
Pri Pri
Pri Pri
B
Chem. Commun. 735 7372008 -, , 6 ,
Phosphite-Phosphoramidite Ligand Library : Allylic SubstitutionPd
PÀMIES, O.; DIÉGUEZ, M.
MF
R
OAc
R R ∗
Nu
RH-Nu
[Pd(π-C3H5)Cl]2 / L*∗
∗O
NR2
R3
R1
P
P
O
O
OO
L*
Chem. Eur. J. 944 9602008 14 -, , 4 ,
Chelated Amino Acid Ester Enolates for Allylic AlkylationPd
KAZMAIER, U.; STOLZ, D.; KRÄMER, K.; ZUMPE, F. L.
MF
X
Z
COOtBu
NHTFA
COOtBu
NHTFATfaN
ZnO
OtBu[Pd(π-C3H5)Cl]2 / PR3
or or
Chem. Eur. J. 1322 13292008 14 -, , 4 ,
Tandem Reaction under Microwave for Synthesis of IndolesPd
SHORE, G.; MORIN, S.; MALLIK, D.; ORGAN, M. G.
MF
NH2
Br
R Br NH
RR' R'
Pd. Cat
Base
N N
Pd
N
Cl Cl
Cl
PEPPSI-IPr
Chem. Eur. J. 1351 13562008 14 -, , 4 ,
52
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Enantioselective Aza-Claisen Rearrangement Catalyzed by FerrocenylbispalladacyclesPd
JAUTZE, S.; SEILER, S.; PETERS, R.
MF
O
CF3
NR
R'
R'
N O
CF3
RFe
NNPd
OTs
NCCH3
Ph
Ts
Ph
NNPd
OTs
NCCH3
Ts
PhPh
Pd. Cat
Chem. Eur. J. 1430 14442008 14 -, , 5 ,
Oral Contraceptive Desogestrel from Double Heck CouplingPd
TIETZE, L. F.; KRIMMELBEIN, I. K.
MF
MeO
H
H
OtBu
Heck
Heck
IBr
MeO
OtBu
H
1. Pd(OAc)2 / PPh3
2. Palladacycle Cat.
Oral ContraceptiveDesogestrel
Chem. Eur. J. 1541 15512008 14 -, , 5 ,
BisPhosphine Pd complexes for Suzuki CouplingPd
SHELOUMOV, A. M.; TUNDO, P.; DOLGUSHIN, F. M.; KORIDZE, A. A. 572–576
MF
Fe
PdPtBu2
PtBu2ClR
B(OH)2
RX
Pd Cat.
K2CO3, 110 °C
X = Br, Cl
Eur. J. Inorg. Chem. 572 5762008 -, , 4 ,
N-Heterocyclic Carbene Birdged by Pyrazole : Complexes of PdPd
SCHEELE, U. J.; JOHN, M.; DECHERT, S.; MEYER, F.
MF
N NPd Pd
NN
NN
R' R'
RR
PF6-
+
Eur. J. Inorg. Chem. 373 3772008 -, , 3 ,
53
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Regioselective Cross-Coupling of Polybrominated ThiophenesPd
C. M. AMB, S. C. RASMUSSEN
BJL
S Br
Br
Br
SZnCl
Pd(dppf)Cl2 (cat) S Br
Br
S
Pd(dppf)Cl2 (cat)
SMgBr
S
Br
S S
63% 80%
SS S
68%
OMe
MeO B(OH)2
Ni(dppp)Cl2 (cat)
Zn
Eur. J. Org. Chem. 801 8042008 -, , 5 ,
Domino Heck–Diels–Alder ReactionsPd
B. YUCEL, M. NOLTEMEYER, A. DE MEIJERE
BJL
CO2Me
+I
+ CO2t-Bu
Pd(OAc)2 (cat)PPh3 (cat)
K2CO3, Et4NCl80°C, 48h
Ph
CO2Me
CO2t-Bu
d.r.=1.25:1 (69%)
+Ph
CO2t-Bu
MeO2C
d.r.=1.1:1 (6%)
Eur. J. Org. Chem. 1072 10782008 -, , 6 ,
Synthesis of BenzazepinesPd
S. KOTHA, V. R. SHAH
BJL
NHR2
IR1
1. Suzuki2. N-allylation N
R1
R2
RCM
R1
NR2
N
R1
2
1. Aza Claisen2. N-acetylation
Eur. J. Org. Chem. 1054 10642008 -, , 6 ,
Synthesis of 3-Spirocyclopropanedihydro- and -Tetrahydropyridin-4-onesPd
J. REVUELTA, S. CICCHI, A. DE MEIJERE, A. BRANDI
BJL
OHNH
R2
R1
Pd(OAc)2 (cat)
N
O
R1R2
+N
O
R1R2
1:1 (75-95%)
Eur. J. Org. Chem. 1085 10912008 -, , 6 ,
54
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of 2,4-Disubstituted SilolesPd
OHMURA, T.; MASUDA, K.; SUGINOME, M.
CJM
BO
OSiEt2N + R Si
Me2
R
RPd(dba)2 1%PPh3 1.2%
toluene, rt
12 examples71-96% yield
J. Am. Chem. Soc. 1526 15272008 130 -, , 5 ,
Boronic Acids with αααα-Diazocarbonyl Coupling ReactionsPd
PENG, C.; WANG, Y.; WANG, J.
CJM
N2R1
R2
R3
O+ PhB(OH)2
Pd(Ph3P)4 2.5%iPr2NH, BQ
PhMe, 80 °C R1
R2
Ph
O
R39 examples65-97% yield
B
J. Am. Chem. Soc. 1566 15672008 130 -, , 5 ,
Oxidative Heck-Type ReactionsPd
KALYANI, D.; SANFORD, M. S.
CJM
R
PdII
PhSnBu3
CuCl2
PhR
Cl
PdII
PhSnBu3
PhICl2
PhR
Cl
SnCu
J. Am. Chem. Soc. 2150 21512008 130 -, , 7 ,
Alkynes: Pseudohalides in Stille ReactionsPd
SHI, Y.; PETERSON, S. M.; HABERAECKER III, W. W.; BLUM, S. A.
CJM
CO2R2R1 + Bu3SnR3PPh3AuPF6 20%
Pd2dba3 1.3%CO2R2R1
PdII
Au+
R1
R3 SnBu3
CO2R2
AuSn
J. Am. Chem. Soc. 2168 21692008 130 -, , 7 ,
55
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
New Polysilane-Supported Palladium/Alumina Hybrid CatalystsPd
OYAMADA, H.; NAITO, T.; MIYAMOTO, S.; AKIYAMA, R.; H AGIO, H.; KOBAYASHI, S.
AE
Ph OEt
O
Ph OEt
OH
H
H H
H H
PI Pd/PSi on Al2O3
H2 (1 atm), neat, 50°C, 16hquant. + 7 another examples
Org. Biomol. Chem. 61 652008 6 -, , 1 ,
Direct Arylation of Heteroaryl Derivatives with Pd-Catalyzed and Aryl TriflatesPd
Heteroaromatic : furan, thiophene, thiazole, oxazole derivatives
ROGER, J.; DOUCET, H.
AE
YZ
XH R1
RYZ
XAr R1
R
+ ArOTfPd(OAc)2, 2 PPh3
KOAc, DMF, 150°C
15 examples, yield : 28-86%
Org. Biomol. Chem. 169 1742008 6 -, , 1 ,
New Palladium(II) bis(N-Heterocyclic Carbene) ComplexesPd
Preparation and reactivity in Suzuki-Miyaura reaction are described
DINARES, I.; GARCIA DE MIGUEL, C.; FONT-BARDIA, M.; SOLANS, X.; ALCALDE, E.
PB
N
N
Pd
N
N
Br
Br
R R
O
O
OO
Organometallics 5125 51282007 26 -, , 21 ,
Optimized Synthesis of Biphosphine Pd(0) Precursors for Cross-coupling ReactionsPd
Quick and reliable generation of biphosphine catalysts under mild conditions at known concentrations.
MITCHELL, E.A.; BAIRD, M.C.
PB
Pd[PCy3]2 Pd[PMetBu2]2 Pd[PtBu3]2
Organometallics 5230 52382007 26 -, , 21 ,
56
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Pd(II)/Cu(II)-catalysed Hydrohalogenation/Hydroalkoxylation of StyrenesPd
Postulated mechanism involves a Pd hydride formed via a Pd-catalysed aerobic alcohol oxidation.
PODHAJSKY, S.M.; SIGMAN, M.S.
PB
OiPr
RR
5 mol% Pd(MeCN)2Cl25 mol% Cu(bc)Cl2
20 mol% CuCl2, MS
10% iPrOH/DCE, 60°C, O2 balloon
Cu
Organometallics 5680 56862007 26 -, , 23 ,
Role of Pd(0) Sources and Anionic Additives in P-C Bond FormationPd
Mechanistic and synthetic studies.
KALEK, M.; STAWINSKI, J.
PB
Ar X HP
O
OEtOEt
ArP
O
OEtOEt
10 mol% Pd
Et3N, THF, 60°C
additive =nBu4N+,X- (X = Cl, Br, OAc)
+
Organometallics 5840 58472007 26 -, , 24 ,
Pd-Catalysed 1,4-Conjugate Addition of Arylboronic Acids to EnonesPd
BEDFORD, R.B.; BETHAM, M.; CHARMANT, J.P.H.; HADDOW, M.F.; ORPEN, A.G.; PILARSKI, L.T.
PB
Pd Cl
O PR2O
R2
R1
O
R2
R1
Ar2
R = OC6H3-2,4-tBu2
ArB(OH)2+
cat.cat. =
toluene
K3PO4
Organometallics 6346 63532007 26 -, , 25 ,
Convenient Synthesis of PCN and PCP Pincer Palladium(II) ComplexesPd
GONG, J.-F.; ZHANG, Y.-H.; SONG, M.-P.; XU, C.
PB
O
Pd N EtEtCl
PPhPh
O O
Pd P RRCl
PRR
R = Ph or Cy
Organometallics 6487 64922007 26 -, , 25 ,
57
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Overman-Claisen Rearrangement with New P,N-Chelate Complexes of Pd(II) and Pt(II)Pd
DUGAL-TESSIER, J.; DAKE, G.R.; GATES, D.P.
PB
NH O
R1
O
CCl3
NH
R1
P
MN
Mes
ClCl
cat. b
CH2Cl2, 35°C, 24h
a M = Ptb M = Pd
Pt
Organometallics 6481 64862007 26 -, , 25 ,
2-(2-Pyridyl)benzazole Pd Complexes for Mizoroki-Heck ReactionsPd
Best catalytic activities obtained with 2-(2-pyridyl)benzoxazole-PdCl2.
HANEDA, S.; GAN, Z.; EDA, K.; HAYASHI, M.
PB
Br O
OtBu
NN
X
PdCl Cl
O
OtBu2 eq K2CO3
DMF, 120°C, 24h+
X = NH, O, S, NMe
cat. =
Organometallics 6551 65552007 26 -, , 26 ,
Novel Cationic Pd(II) ComplexesPd
More active catalysts in aqueous Suzuki-Miyaura coupling than their neutral couterparts.
HAN, Y.; HUYNH, H.V.; TAN, G.K.
PB
N
NPd I
R
PPh3
PPh3
R X B(OH)2 R
+
OTf-
cat.
H2O
K2CO3+
cat.
Organometallics 6581 65852007 26 -, , 26 ,
Aza-Claisen Rearrangement with New Chiral Pd bis(diaminocarbene) ComplexesPd
WANNIARACHCHI, Y.A.; KOGISO, Y.; SLAUGHTER, L.M.
PB
N N
Pd
Ph Ph
Cl Cl
NH
NH
ArAr
F3C
N O
F3C
N
Ph
O
Ph 5 mol% [Pd]
AgX
degased solution40°C, 2d
[Pd]
Organometallics 21 242008 27 -, , 1 ,
58
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
DFT Study of the Pd-Biphosphine Catalysed Hydrogenation of AlkynesPd
Neutral and cationic pathways are considered.
LOPEZ-SERRANO, J.; LLEDOS, A.; DUCKETT, S.B.
PB
R R' RR'H2, Pd
biphosphine
Organometallics 43 522008 27 -, , 1 ,
DFT Study of the Wacker OxidationPd
BEYRAMABADI, S.A.; ESHTIAGH,-HOSSEINI, H.; HOUSAINDOKHT, M.R.; MORSALI, A.
PB
C2H4 + 1/2 O2
PdCl2 / CuCl2
H2OCH3CHO
Cu
Organometallics 72 792008 27 -, , 1 ,
High Regioselectivity in Cyanothiolation of 1-Alkynes : a DFT StudyPd
ZHENG, W.; ARIAFARD, A.; LIN, Z.
PB
R
PhS CN+ PhSCN
[Pd]
Organometallics 246 2532008 27 -, , 2 ,
Tunable Metalloporphyrin-derived Precatalysts - Application in Heck ReactionPd
Catalytic activity : M = MnCl < 2H < Ni < Mg
SUIJKERBUIJK, B.M.J.M.; HERRERAS MARTINEZ, S.D.; VAN KOTEN, G.; KLEIN GEBBINK, R.J.M.
PB
NM
NN
N
Ar
Ar
Ar
Pd
S
S
Cl
Ph
PhPh
Ar
PhI +
0.2 mol%[Pd]Et3N, DMF, 119°C
M = 2H, Mg, MnCl, Ni
MnNiMg
Organometallics 534 5422008 27 -, , 4 ,
59
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
New N-Heterocyclic Carbene Sulfonamide Pd ComplexesPd
Acetate-coordinated Pd complexes are effective catalysts for Suzuki-Miyaura coupling reactions
ZHANG, T.; WANG, W.; GU, X.; SHI, M.
PB
N N
NPd
S O
OR
L R = Me or Me-C6H5
L = I or OAc
Organometallics 753 7572008 27 -, , 4 ,
Poly(arylenevinylene)s.Pd
8 examples.
PRUKALA, W.; PAWLUC, P.; POSALA, K.; MARCINIEC, B.
MJ
Me2Si
O O
SiMe2+ n XArX
X = I, Br
Pd2(dba)3 (0.01 eq.)TBAF (2.4 eq.)
dioxane, 80 °C, 16-48 h35-98%
Ar
nn
Si
Synlett 41 442008 -, , 1 ,
Arylation of Porphyrin Derivatives.Pd
15 examples. Various L tested.
ARTAMKINA, G.A.; SAZONOV, P.K.; SHTERN, M.M.; GRISHINA, G.V.; VESELOV, I.S.; SEMEIKIN, A.S.; SYRBU, S.A.;KOIFMAN, O.I.; BELETSKAYA, I.P.
MJ
Porphyrin Br HN OH+
Pd(OAc)2/L (cat.)t-BuONa (excess)
dioxane, 100 °C, 20 h
up to 70%
Porphyrin N OH
Synlett 45 482008 -, , 1 ,
Sonogashira Coupling.Pd
7 examples.
DOI, T.; ORITA, A.; MATSUO, D.; SAIJO, R.; OTERA, J.
MJ
PhSO2
I
Br
OMe
Pd(PPh3)4 (cat.)CuI (cat.)
(i-Pr)2NHPhMe, rt
88%
PhSO2
Br
OMe
+
Cu
Synlett 55 602008 -, , 1 ,
60
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Four-Component Coupling.Pd
Also with amidines instead of hydrazines to give pyrimidines.
STONEHOUSE, J.P.; CHEKMAREV, D.S.; IVANOVA, N.V.; LANG, S.; PAIRAUDEAU, G.; SMITH, N.; STOCKS, M.J.;SVIRIDOV, S.I.; UTKINA, L.M.
MJ
PhI + + H2NNHMe + Mo(CO)6
Pd(OAc)2 (0.05 eq.)P(t-Bu)3 (0.1 eq.)
CuI (0.02 eq.)
Cs2CO3 (2.5 eq.)PhMe/MeCN80 °C, 18 h
Ph
Ph
Me
Ph
63%
MoCu
Synlett 100 1042008 -, , 1 ,
Suzuki Coupling.Pd
20 examples. Various conditions tested.
BARANCELLI, D. A.; ALVES, D.; PREDIGER, P.; STANGHERLIN, E. C.; NOGUEIRA, C. W.; ZENI, G.
MJ
Se
I
R2R1
+ R3B(OH)2
Pd(OAc)2 (0.05 eq.)K3PO4/H2O
DME, reflux, 1-15 h47-96%
Se
R3
R2R1
B
Synlett 119 1252008 -, , 1 ,
Heck Reaction, Total Synthesis of Sylvone.Pd
NASVESCHUK, C. G.; ROVIS, T.
MJ
O
O
OMeMeO
IMeO
MeO
OMe
+
Pd(OAc)2 (cat.)BnEt3NCl
i-Pr2NEtDMF, 80 °C
45%, >95;5 dr
O
O
OMeMeO
MeO
MeO
OMe
Synlett 126 1282008 -, , 1 ,
Base-Free Suzuki Reaction.Pd
22 examples.
BASU, B.; DAS, S.; KUNDU, S.; MANDAL, B.
MJ
Ar X +
X = I, Br, Cl
NaBPh4or
NR3
ArPh71-96%
Pd(OAc)2 (0.02 eq.)
DMF or H2O, 85 °C, 2-8 hBPh4
B
Synlett 255 2592008 -, , 2 ,
61
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Microwave-Activated Pd-cat Intramolecular Cyclisation of Electron-Rich HeterocyclesPd
BECALLI, E.M.; BROGGINI, G.; MARTINELLI, M.; SOTTOCORNOLA, S.
PG
X N
I
CO2EtX N
CO2Et
Pd(OAc)2PPh3AcOK
DMAµW 450 W , 1h
9 examples 33-80% yield
Synthesis 136 1402008 -, , 1 ,
Microwave-Assisted Three-Component Synthesis of IsoxazolesPd
WILLY, B.; ROMINGER, F.; MULLER, T. J. J.
PG
O
R1 ClR2+
PdCl2(PPh3)2 (2 mol%)CuI (4 mol%)Et3N (1 equiv)
THF, rt, 1h
N
Cl R3
OH
Et3N (1.1 equiv)30 min, µW, 90°C
ONR2
R3R1
O
24 examples 12-78% yield
Synthesis 293 3032008 -, , 2 ,
Sonogashira Couplings Unsing an Acetylene EquivalentPd
CSEKEI, M.; NOVAK, Z.; KOTSCHY, A.
LE
OH 1- Ar1X, cat. CuI, cat. Pd(II), (i-Pr)2NH75-99%
2- Ar2X, cat. CuI, cat. Pd(II), (i-Pr)2NH, KOH33-95%
Ar1 Ar2
Cu
Tetrahedron 975 9822008 64 -, , 6 ,
Synthesis of Fused Pyran RingsPd
JANA, R.; SAMANTA, S.; RAY, J.K.
TJ
O
X
Br O
R'
R
OMe
R'
Pd(OAc)2PPh3, Cs2CO3
TBAC, DMF80-85 °C
Pd(OAc)2PPh3, Cs2CO3
TBAC, DMF80-85 °C
R = X = H
R'R = Me
X = CH2, O65-75% 55-65%
Tetrahedron Lett. 851 8542008 49 -, , 5 ,
62
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of 2,2-Diaryl-1,1-difluoroethenesPd
CHOI, J.H.; JEONG, I.H.
TJ
F
F SO2Ph
Ph F
F SnBu3
PhF
F
Ph
R
ArI 3 equiv.Pd(PPh3)4/CuI
DMF, 80 °C, 5-9 h
22-82%R = H, X, OCH3, CH3, CF3, NO2
Bu3SnH 4 equiv.AIBN
benzene, reflux5 h 60%
Sn
Tetrahedron Lett. 952 9552008 49 -, , 6 ,
Synthesis of Thiophene DerivativesPd
ARAI, N.; MIYAOKU, T.; TERUYA, S.; MORI, A.
TJ
S
Br
BrS
Ar1
Ar1
S
Ar1
Ar1
Pd(OAc)2 5 mol%PPh3 20 mol%K2CO3 3 equiv.
THF-H2O, reflux, 10 h
Ar2
Ar2I, Pd cat. (3-5 mol%)
AgNO3-KFDMSO,
100 °C, 24 h
Ar1 BO
O
6 examples83-99%
10 examples37-86%
Tetrahedron Lett. 1000 10032008 49 -, , 6 ,
Regioselective C-2 Arylation of HeterocyclesPd
NANDURKAR, N.S.; BHANUSHALI, M.J.; BHOR, M.D.; BHANAGE, B.M.
TJ
Z
YX
R Z
Y
RK3PO4, NMP125 °C, 36 h
Pd(TMHD)2 10 mol%+ 16 examples
35-96%
(Y = CH, Z = NMe, O, S) (Y = N, Z = O, S)X = I, Br; R = Me, OMe, NO2
Tetrahedron Lett. 1045 10482008 49 -, , 6 ,
Suzuki-Miyaura CouplingPd
YU, S.-B.; HU, X.-P.; DENG, J.; HUANG, J.-D.; WANG, D.-Y.; DUAN, Z.C.; ZHENG, Z.
TJ
Cl B(OH)2
R R+
Pd(OAc)2/LK3PO4
Fe PPh2
N
N N
N
OMe
OMe
R Rdioxanereflux, 12 h
L =
9 examples95-99%
BFe
Tetrahedron Lett. 1253 12562008 49 -, , 7 ,
63
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Palladium-Catalyzed Suzuki Cross-Coupling Reactions in a MicroemulsionPd
VASHCHENKO, V.; KRIVOSHEY, A.; KNYAZEVA, I.; PETRENKO, A.; GOODBY, J.W.
TJ
PdCl2(dppf)NaHCO3, SDS
H2O/PhMe/BuOH18 h
6 examples28-100%
R B(OH)2
n
Br R'
m
+ R R'
k
R = R' = H, Alkk = 2,3
Tetrahedron Lett. 1445 14492008 49 -, , 9 ,
Palladium-Catalyzed Asymmetric Allylic SubstitutionPd
XIE, F.; LIU, D.; ZHANG, W.
TJ
M
PPh2
PPh2
CO2R
CO2R
M
PPh2
PPh2
CH2OR
CH2OR
Ph Ph
Nu
M = Fe, RuR = H, Ac, Me
M = Fe, RuR = Ac, Me
(S)Ph Ph
Nu
(R)
Ph Ph
OAc
rac-
i: Pd(II), HNuCH2Cl2, 20 °C, 20 mn
up to 99% ee up to 88% ee
i i
FeRu
Tetrahedron Lett. 1012 10152008 49 -, , 6 ,
[H 2PtIVV9O28]5– : a POM Containing a Late Transition Metal in High Oxidation StatePt
LEE, U.; JOO, H.-C.; PARK, K.-M.; MAL, S. S.; KORTZ, U.; KEITA, B.; NADJO, L.
CYAngew. Chem. Int. Ed. 793 7962008 47 -, , 4 ,
[4+3] Cycloaddition of 1,3-Dienes with AllenesPt
TRILLO, B.; LOPEZ, F.; GULIAS, M.; CASTEDO, L.; MASCARENAS, J. L.
CY
EtO2CEtO2C
EtO2CEtO2C
PtCl2 (10 mol%), toluene, 23 ºC, 18 h
95%
Angew. Chem. Int. Ed. 951 9542008 47 -, , 5 ,
64
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Cis-[(1,2-camphordiamine)dichloro]platinum(II) ComplexesPt
The cytotoxicity of Pt-complexes against the HL-60 cell line was studied.
MONTANA, A. M.; BERNAL, F. J.; LORENZO, J.; FARNOS, C.; BATALLA, C.; PRIETO, M. J.; MORENO, V.; AVILES, F. X.;MESAS, J. M.; ALEGRE, M. T.
PL
NH3+Cl-
NH3+Cl-
R1
R2
NH2
NH2
R1
R2
Pt
Cl
Cl
K2PtCl4
H2O, rt, 1h
R1, R2 = H, Me
Bioorg. Med. Chem. 1721 17372008 16 -, , 4 ,
n-Alkanes DehydrogenationPt
Cs and Na cations titrate acid sites and inhibit isomerization and cracking side reactions
X. LI, E. IGLESIA
BPH
R1 R2
R1 R2catcat: Pt clusters within [Fe]ZSM-5 channels
673-743 K
Fe
Chem. Commun. 594 5962008 -, , 5 ,
Transmetalation from Tin to IridiumPt
SMITH, S. E.; SASAKI, J. M.; BERGMAN, R. G.; MONDLOCH, J. E.; FINKE, R. G.
CJM
Cp*
IrPMe3 Cl
Cl+ PhxSnMe4-x
Cp*
IrPMe3 Ph
ClPt(PtBu3)2 10%
75 °Cor
Cp*
IrPMe3 Me
Cl
SnIr
J. Am. Chem. Soc. 1839 18412008 130 -, , 6 ,
Olefin OxidationPt
KHUSNUTDINOVA, J. R.; NEWMAN, L. L.; ZAVALIJ, P. Y.; LAM, Y.; VEDERNIKOV, A. N.
CJM
NPt
N
OH
O-
+R R R R
OH2O, rt
J. Am. Chem. Soc. 2174 21752008 130 -, , 7 ,
65
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
One-pot Synthesis of (L)Pt(0)(1,6-diene) Complexes from H 2PtCl6Pt
BERTHON-GELLOZ, G.; SCHUMERS, J.-M.; LUCACCIONI, F.; TINANT, B.; WOUTERS, J.; MARKO, I.E.
PB
EtO2C
EtO2C Pt iPr
O
Pt PPh3
IPr = 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidone
Organometallics 5731 57342007 26 -, , 23 ,
Effects of Additives and L/Cu Ratio in Alkynylation of αααα-Imino EsterCu
SHAO, Z.; WANG, J.; DING, K.; CHAN, A.S.C.
AF
N
CO2EtH
PMP
Ph
Ph
NHPMP
CO2Et*
CuOTf.0.5C6H6 / 8 (10 mol %)
CH2Cl2r.t.
ratio 8 / Cu 1 : 1 80 % 63 % ee 1.5 : 1 60 % - 70 % ee
+ NN
OO
N
Ph Ph
8:
Adv. Synth. Catal. 2375 23792007 349 -, , 14-1
,
Protodecarboxylation of Aromatic Carboxylic AcidsCu
GOOßEN, L.J.; THIEL, W.R.; RODRIGUEZ, N.; LINDER, C.; MELZER, B.
AF
up to 90 % isolated yield
Ar CO2H Ar H + CO2
Cu / L (10 mol %)
NMP / quinoline170 °C
12 - 24 h
Cu = Cu2OL = 1,10-phenanthroline or 4,7-diphenyl-1,10-phenanthroline21 ex.
Adv. Synth. Catal. 2241 22462007 349 -, , 14-1
,
Nanocrystalline Copper(II) Oxide in Asymmetric Hydrosilylation of KetonesCu
Optimization of the reaction conditions. Variation of the silane.
KANTAM, M.L.; LAHA, S.; YADAV, J.; LIKHAR, P.R.; SREEDHAR, B.; CHOUDARY, B.M.;
AF
O
R1R+ PhSiH2
Nano-CuO (0.01 g)(S)-BINAP
Toluene- 20 °C, 2.5 - 9 h
73 - 99 % ee
TBAF
Ether
OH
R1R
2 mmol 2 equiv
R = arylR1 = Me, Et
Si
Adv. Synth. Catal. 1797 18022007 349 -, , 10 ,
66
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Polymer-Supported Fesulphos Ligands Applied in Asymmetric CatalysisCu
Synthesis of two polystyrene supported ligands reported. Other substrates used.
MARTIN-MATUTE, B.; PEREIRA, S.I.; CABRERA, E.-P.; ADRIO, J.; SILVA, A.M.S.; CARRETERO; J.C.
AF
N
Ph
CO2Me
+ N
O
O
Ph
1.1 equiv NH
NO O
Ph CO2Me
PhL* (3 mol %)Cu(CH3CN)4ClO4
(3 mol %)
Et3N (18 mol %)CH2Cl2
- 10 °C, 4 h98 %, > 99% ee
Fe
StBu
PPh2
O
L*:
Adv. Synth. Catal. 1714 17242007 349 -, , 10 ,
Asymmetric Cu-Catalyzed Carbenoid Insertion into O-H Bond of WaterCu
ZHU, S.-F.; CHEN, C.; CAI, Y.; ZHOU, Q.-L.
PG
ArO
R
N2
O
+ H2O
CuSO4 (5 mol%)Ligand* (6 mol%)NaBArF (6 mol%)
CHCl340°C, 30 min
ArO
R
O
OH
R = Me, Et, i-Pr, Bn20 examples71-91% yield36-94 % ee
N
O
O
N Ph
Ph
Ligand* :
Angew. Chem. Int. Ed. 932 9342008 47 -, , 5 ,
Cu-Catalyzed Addition of Diboron Reagents to αααα,ββββ-Acetylenic EstersCu
LEE, J.-E.; KWON, J.; YUN, J.
MD
65-99% yields
R CO2Et
CuCl (3 mol%)t-BuONa (6 mol%)
xantphos (3 mol%)
THF, r.t., 24h
BpinCO2Et+ B2pin2
7 examples
Chem. Commun. 733 7342008 -, , 6 ,
New Reusable Cu-Catalyst for the Huisgen CycloadditionCu
CANDELON, N.; LASTÉCOUÈRES, D.; DIALLO, A. K.; ARANZAES, J. R.; ASTRUC, D.; VINCENT, J.-M.
MD
R1 N3 + R2L (0.01-0.1 mol%)
solvent, 60°C, 24h
NN
NR1
R2
62-94% yields14 examples
N
NC18H37
C18H37
Cu N
NC18H37C18H37
C18H37
C18H37
Br
L =
Chem. Commun. 741 7432008 -, , 6 ,
67
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Cu-Catalyzed Cross-Coupling of Thiols with Aryl HalidesCu
ROUT, L.; SAHA, P.; JAMMI, S.; PUNNIYAMURTHY, T.
MD
X
Y
+
CuI (1 mol%)TBAB (1 equiv))
KOH (1.5 equiv)
H2O, air, 80°C
RSH
X
SR
15-99%18 examplesR = alkyl, aryl, benzyl
Y = I, Br, Cl
X = H, NO2
Eur. J. Org. Chem. 640 6432008 -, , 4 ,
Copper-Catalyzed Aerobic Synthesis of YnamidesCu
HAMADA, T.; YE, X.; STAHL, S. S.
PG
R HNR'
EWG
+
CuCl2 (20 mol%)Pyridine 2 equiv.Na2CO3 2 equiv.
O2 1 atm
Toluene70°C, 4 h
R N
EWG
R'
41 examples51-95 % yield
J. Am. Chem. Soc. 833 8352008 130 -, , 3 ,
Copper-Catalyzed Arylation of PolyfluoroareneCu
DO, H.-Q.; DAUGULIS, O.
PG
F
F
F
F
F
H
+ ArBr
CuI (10 mol%)Phenantroline (10 mol%)
K3PO4 2 equiv.
DMF/Xylene120-140°C
F
F
F
F
F
Ar
11 examples65-95%
J. Am. Chem. Soc. 1128 11292008 130 -, , 4 ,
Copper-Catalyzed Diamination of 1-Halo-1-alkynesCu
FUKUDOME, Y.; NAITO, H.; HATA, T.; URABE, H.
PG
R
Br
Ts
N
Ts
N
+
CuI (5 mol%)(CH2NHMe)2
K3PO4
DMF110°C, 14 h
Ts
N
Ts
N
R
9 examples47-77% yield
J. Am. Chem. Soc. 1820 18212008 130 -, , 6 ,
68
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Immobilized Metal Ion-containing Ionic Liquids Cu
ImmCu2+-IL, ImmPd2+-IL reusable more active catalysts than unsupported counterparts.
SASAKI, T.; TADA, M.; ZHONG, C.; KUME, T.; IWASAWA, Y.
PLA
N NSiOMeO
O+
MClx
SiO2
M = Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Pd2+, Pt2+
ImmM-IL =Pd
J. Mol. Catal. A 200 2092008 279 -, , 2 ,
Addition of Active Methylenes to Alkenes in Ionic Liquids or Solventless ConditionsCu
Use of environmentally friendly reaction media.
LANMAN, H. E.; NGUYEN, R.-V.; YAO, X.; CHAN, T.-H., LI, C.-J.
PLA
Ar+
R1
R1
O
O Ar
R1
R1
O
O
10 % Cu(OTf)2, no solvent
10 % SnBr4, ionic liquidsor
conditionsconditions :
12 examples up to 85 % yield
Sn
J. Mol. Catal. A 218 2222008 279 -, , 2 ,
Synthesis of CarbanucleosidesCu
Feature article; 4 examples; study of reaction conditions.
BROGGI, J.; DIEZ-GONZALEZ, S.; PETERSEN, J.L.; BERTEINA-RABOIN, S.; NOLAN, S.P.; AGROFOGLIO, L.A.
GJ
OH
OH
OH
N3
NN
N
OH
OH
OH
+
75%
Cu(0)/CuSO4 (4:1 mol%)
1:1 t-BuOH/H2O
microwaves, 5 d
Synthesis 141 1482008 -, , 1 ,
Synthesis of Propargylic Ethers and SulfidesCu
21 examples, yields: 38-98%.
HUI, H.H.; ZHAO, Q.; YANG, M.Y.; SHE, D.B.; CHEN, M.; HUANG, G.S.
GJ
CH3
CH3
OH
CH3
O
CH3
+ n-BuOHCuBr2 (5 mol%)
MeNO2, rt, 5 h98%
Synthesis 191 1962008 -, , 2 ,
69
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Three-Component Synthesis of 1,2-DihydroisoquinolinesCu
Diethylphosphite and nitromethane were also introduced instead of the alkyne.
YE, Y.; DING, Q.; WU, J.
LE
CHO
PhAr NH2 R++
N
R
Ph
ArCuSO4 (10 mol%)C12H25SO3Na (10 mol%)
H2O, )), 36-98%
Tetrahedron 1378 13822008 64 -, , 7 ,
N-Arylation of Nitrogen-Containing HeterocyclesCu
MAO, J.; GUO, J.; SONG, H.; JI, S.-J.
LE
Ar X Het-NH+
Cu(OAc)2.H2O (20 mol%)Hippuric acid (20 mol%)
DMF, Cs2CO3, 32-99%Ar N-Het
Het = Im, Indole,Pyrrole,...
Tetrahedron 1383 13872008 64 -, , 7 ,
Copper-Catalyzed N-Arylation of Imidazole, Benzimidazole and PyrazoleCu
MAHESWARAN, H.; KRISHNA, G. G.; PRASANTH, K. L.; SRINIVAS, V.; CHAITANYA, G. K.; BHANUPRAKASH, K.
LE
Ar X Het-NH+ Ar N-Het[Cu2I2((-)sparteine)2] (5 mol%)
DMSO, K2CO3, 65-96%
Tetrahedron 2471 24792008 64 -, , 10 ,
Colorimetric and Fluorescent Sensors for Cu2+Cu
The receptors show a fluorescence modulation and a major colour change when bound to Cu2+.
MARTINEZ, R.; ESPINOSA, A.; TARRAGA, A.; MOLINA, P.
LE
Ar
HN NH
Tetrahedron 2184 21912008 64 -, , 9 ,
70
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Triskelion Peptide as a Fluorescent Sensor for Cu2+Cu
Fluorescence is quenched when the peptide is bound to Cu2+.
GHOSH, S.; SINGH, P.; VERMA, S.
LE
NNH
O NH
NH
ONH2
HN
3
Tetrahedron 1250 12562008 64 -, , 7 ,
A Facile Synthesis of 1,5-EnynesCu
YADAV, J.S.; REDDY, B.V.R.; RAO, T.S.; RAO, K.V.R.
TJ
OH
R1
R2
R3
SiMe3+
10 mol% Cu(BF4)2or 5 mol% Sc(OTf)3
MeCN, rt R1
R2
R3 16 examples78-86%
R1 = Ar, StyrylR2 = Alk, ArR3 = H, Me
Sc
Tetrahedron Lett. 614 6182008 49 -, , 4 ,
Copper Catalyzed Synthesis of N-Substituted FerrocenesCu
PURECHA, V.H.; NANDURKAR, N.S.; BHANAGE, B.M.; NAGARKAR, J.M.
TJ
FeN-Het
+ HN-HetCu(TMHD)2 10 mol%
KOt-Bu, DMSO90 °C, 12 h
FeX
16 examples14-95%
Fe
Tetrahedron Lett. 1384 13872008 49 -, , 8 ,
Silver Chalcogenide ClustersAg
ANSON, C. E.; EICHHÖFER, A.; ISSAC, I.; FENSKE, D.; FUHR, O.; SEVILLANO, P.; PERSAU, C.; STALKE, D.; ZHANG, J.
CY
Synthesis and Crystal Structures of [Ag154Se77(dppxy)18],
[Ag320(StBu)60S130(dppp)12],
[Ag352S128(StC5H11)96], and
[Ag490S188(StC5H11)114]
Angew. Chem. Int. Ed. 1326 13312008 47 -, , 7 ,
71
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Ring-Opening of Unactivated Vinylcyclopropanes with SulfonamidesAu
SHI, W.-J.; LIU, Y.; BUTTI, P.; TOGNI, A.
AF
R3
R1 R2
+ TsNHMeAuPPh3 (10 mol %)
toluene50 °C, 24 h R3 NMeTs
R1 R3
R1, R2 = H, Me, PhR3 = p-Me-C6H4, p-(t-Bu)-C6H4, p-Cl-C6H4, p-F-C6H4, p-OMe-C6H4, 2-naphtyl, phenylethyl, Ph, H, cyclohexyl
10 - 99 %
3 equiv
Adv. Synth. Catal. 1619 16232007 349 -, , 10 ,
Synthesis of Oxepines from γγγγ-AlkynylfuransAu
HASHMI, A.S.K.; KURPEJOVIC, E.; WÖLFLE, M.; FREY, W.; BATS, J.W.
AF
37 % isolated
OOBr
OOBr Br
O
O7 (5 mol %)
CH2Cl2r.t., 10 min
N
Au OClCl
7:
Adv. Synth. Catal. 1743 17502007 349 -, , 10 ,
Tandem Cycloisomerization of Alkynyloxiranes with NucleophilesAu
SHU, X.-Z.; LIU, X.-Y.; XIAO, H.-Q.; JI, K.-G.; GUO, L.-N.; QI, C.-Z.; LIANG, Y.-M.
AF
OAc
R1 OR2
+ MeOH"Au" (2 mol %)
"Au" = AuCl3 , r.t. or AuCl4.4 H2O, 60 °C
OR1OMe
R2
R1 = Ph, p-Cl-C6H4, m-Cl-C6H4, m-CH3-C6H4, p-CH3O-C6H4, 2-thienyl, n-C5H11
R2 = Ph, p-CH3-C6H4, H0.5 - 4 h 57 - 96 %
PdCuAg
Adv. Synth. Catal. 2493 24982007 349 -, , 16 ,
Equilibrium of Cationic Gold Complexes from Propargylic Esters: a Theoretical StudyAu
CORREA, A.; MARION, N.; FENSTERBANK, L.; MALACRIA, M.; NOLAN, S. P.; CAVALLO, L.
CY
O
O
O
O
[Au]+O
O
O O
[Au]+[Au]+
[Au]+
Angew. Chem. Int. Ed. 718 7212008 47 -, , 4 ,
72
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Shape and Size Controlled Growth of Gold NanocrystalsAu
SEO, D.; YOO, C. I.; PARK, J. C.; PARK, S. M.; RYU, S.; SONG, H.
CY
Cubes, Cuboctahedra and Octahedra shaped crystals were obtained
Angew. Chem. Int. Ed. 763 7672008 47 -, , 4 ,
Au- or In-Catalyzed Cyclization of ortho-Alkynyl-N- sulfonylanilinesAu
NAKAMURA, I.; YAMAGISHI, U.; SONG, D.; KONTA, S.; YAMAMOTO, Y.
PG
NSO2R
2
RY
R1
Cat AuBr3
Y =H
Cat InBr3
Y =OMeN
ROMe
N
R
SO2R2
H
R1
R2O2S
R1
In
Chem. Asian J. 285 2952008 3 -, , 2 ,
Single-step Synthesis of Gold–Silver Alloy Nanoparticles in Ionic LiquidsAu
K.-I. OKAZAKI, T. KIYAMA, K. HIRAHARA, N. TANAKA, S. KUWABATA, T. TORIMOTO
BJL
Simultaneous sputter deposition of gold and silver onto ionic liquids formed alloy nanoparticles. During the sputter deposition under vaccum, the bombardment of a metal target, with energetic gaseous ions causes the physicalejection of surface atoms and/or small metal clusters. Sputtered metal species are injected into ILs without gas-phase collisions in the space between the target and IL solution.
Ag
Chem. Commun. 691 6932008 -, , 6 ,
Styrene PolymerizationAu
J. URBANO, A. J. HORMIGO, P. DE FRÉMONT, S. P. NOLAN, M. M. DIAZ-REQUEJO, P. J. PÉREZ
BJL
Br Pd Br
NNPri Pri
Pri Pri
Au (cat)
NaBAr4
rt, minutes
atactic polystyrene60-90% Au (cat):
Br
Chem. Commun. 759 7612008 -, , 6 ,
73
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Cycloisomerization of Hydroxylated 1,5-Allenynes : Pt vs AuAu
ZRIBA, R.; GANDON, V.; AUBERT, C.; FENSTERBANK, L.; MALACRIA, M.
MF
.
HOR
R = SiMe3R = (CH2)nOTBS
1. PtCl4 cat.
2. TBAF
AuCl(PPh3)2 2 mol%
AgSbF6 2 mol% O
SiMe3
O
H
OHn
Pt
Chem. Eur. J. 1482 14912008 14 -, , 5 ,
Synthesis of Unsymmetrical Ethers from AlcoholsAu
CUENCA, A. B.; MANCHA, G.; ASENSIO, G.; MEDIO-SIMÓN, M.
MF
R1 OH R2 OH R1 OR2
H2O
NaAuCl4 Cat.
R1 = benzylic, alkyl R2 = Alkyl
70-85 °C
Chem. Eur. J. 1518 15232008 14 -, , 5 ,
Alkenes Hydroamination: MechanismAu
KOVACKS, G.; UJAQUE, G.; LLEDOS, A.
CJM
+ H2N OR
OR3PAuOTf H2N
O
OR
AuPR3
H+
tansfer
HN
O
OR
J. Am. Chem. Soc. 853 8642008 130 -, , 3 ,
[4+2] AnnulationAu
ZHANG, G.; HUANG, X.; LI, G.; ZHANG, L.
CJM
R3
R1
O
R2
(NHC)AuNTf2
OR2 R1
[Au]
R3
OR2 R1
R3
+ orX
J. Am. Chem. Soc. 1814 18152008 130 -, , 6 ,
74
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Furans From Allenyl SystemsAu
DUDNIK, A. S.; SROMEK, A. W.; RUBINA, M.; KIM, J. T.; KEL’IN, A. V.; GEVORGYAN, V.
CJM
Y
R1
R2X
R3 Au-, Cu-, Ag-....cat. 1,2 shift
XR1 R3
R2Y 51 examplesY= X, S, Se, C53-100% yield
AgCu
J. Am. Chem. Soc. 1440 14522008 130 -, , 4 ,
Gold Nanoparticles Colloid-stabilized and their Application in Catalysis.Au
Gold nanoparticles are stabilized with poly(N-isopropylacrylamide)-co-poly(4-vinyl pyridine) colloids.
WANG, Y.; WEI, G.; WEN, F.; ZHANG, X.; ZHANG, W.; SHI, L.
BP
HO NO2 HO NH2
(λ = 400 nm) (λ = 290 nm)
Colloid-stabilized Au nanoparticles cat.
NaBH4
J. Mol. Catal. A 1 62008 280 -, , 1-2,
Gold(I)-Catalysed Claisen -Type RearrangementAu
A mechanism is proposed.
ISTRATE, F.M.; GAGOSZ, F. L.
LS
R3
O R5
R4
R2R1
O
R3R2
R1
R4 R5O
R3R2
R1 AuR4
R5(p-CF3-C6H4)3P-Au-NTf2 (2 mol%), DCM, rt, 10 min
19 Examples
Yields : 17 - 100%R1, R2, R3 and R4 = H, alkyl, phenyl, alkenyl
J. Org. Chem. 730 7332008 73 -, , 2 ,
Au I-Catalyzed CyclisationAu
Oxydation of the products is carried out using MnO2 to obtain aurone.
HARKAT, H.; BLANC, A.;WEIBEL, J.-M.;PALE, P.
LS
R
OH
R'
OH
AuCl (1 mol%), K2CO3 (10 mol%)
MeCN, rt
R
O
R'
OH
Yield : 65 - 86%
8 ExamplesR = H, NO2, Br, OMe
R' = H, Cl, OMe
J. Org. Chem. 1620 16232008 73 -, , 4 ,
75
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Chiral Elaboration of Gold Nanoparticle Surfaces.Au
NURUZZAMAN, M.; PRESTON, T. C.; MITTLER, S.; JONES, N. D.
MJ
Example of the supportthat has been synthesised:
OH
ON
O
(CH2)10
HS
HO
Synlett 207 2122008 -, , 2 ,
Silica-Supported Chiral BINOL as Ligand for Enantioselective CatalysisZn
Reusable ligand
PATHAK, K.; AHMAD, I.; ABDI, S. H. R.; KURESHY, R. I.; KHAN, N.-U. H.; JASRA, R. V.
PLA
NSiO
OSiO2 O
3
O
OHOH
O
R+ Et2Zn
OHLigand / Ti(OiPr)4
Ligand :
6 examples up to 94 % yield and 94 % ee
R
Ti
J. Mol. Catal. A 106 1142008 280 -, , 1-2,
Tandem Michael Addition / [3,3]-Rearrangement Reaction of Allyl FumaratesZn
A Curtius Rearrangement of the resulting succinate is also described.
BAUSCH, C. C.; JOHNSON, J. S.
LE
OAll
O
O
O
1- R2Zn, TMSClCu(NtBu.sal)2 cat.
Et2O
2- Me2SO4, K2CO363-88%
OAll
O
O
OMe
RCu
J. Org. Chem. 1575 15772008 73 -, , 4 ,
Computational Study of Deprotonation with TMP-Zn-ate/TMEDA ComplexZn
DFT Calculations were performed.
NOBUTO, D.; UCHIYAMA, M.
LE
N
ZnRR
N
N
Na
Na
J. Org. Chem. 1117 11202008 73 -, , 3 ,
76
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Synthesis of 1,4-Disubstituted Benzenes Through Two Sequential Negishi CouplingsZn
Chemoselectivity is obtained thanks to the use of Pd-P(tBu)3 as the catalyst.
KAWAMOTO, T.; EJIRI, S.; KOBAYASHI, K.; ODO, S.; NISHIHARA, Y.; TAKAGI, K.
LE
ZnI
IZn
R1-X
Pd-P(t-Bu)3 cat., rt
R1
IZn
R2-X, rtR1
R255-78%
Pd
J. Org. Chem. 1601 16042008 73 -, , 4 ,
Asymmetric Addition of Organozinc Reagents to N-Formyl IminesZn
PIZZUTI, M. G.; MINNAARD, A. J.; FERINGA, B. L.
LE
R NH
Ts
O
HEt2Zn (2.5 eq.)Cu(OTf)2 (2 mol%)(S,R,R)-L (4 mol%)
R NH
O
H
THF, -50°C
up to 99% yield and ee
(S,R,R)-L =
O
OP N
Ph
Ph
Cu
J. Org. Chem. 940 9472008 73 -, , 3 ,
Synthesis of Aminoxy PseudoglycalsZn
8 examples, yields: 78-96% (high α-selectivity).REDDY, CH.R.; RAO, Y.S.; KUMAR, T.P.; REDDY, K.V.; CHANDRASEKHAR, S.
GJ
OAcO
OAc
AcO
N
O
O
OHN
O
O
OOAcO
AcO
+ZnCl2 (2 mol%)
CH2Cl2, rt, 2.5 h
96% (α/β 50:1)
Synthesis 122 1262008 -, , 1 ,
Cr-Aminoborylene Complex-Catalyzed Demercuration of Bis(alkynyl)mercurialsHg
Comparison between catalytic and stoechiometric reactions
APOSTOLICO, L.; BRAUNSCHWEIG, H.; CRAWFORD, A. G.; HERBST, T.; RAIS, D.
MVI
HgAr Ar Ar Ar
[(CO)5Cr=B=N(SiMe3)2](10 mol%)
C6H6, 90°C
4 examples51-66% yield
Chem. Commun. 497 4982008 -, , 4 ,
77
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Cephalothin-Analogue Boronic AcidsB
Boronic acids have proved to be promising selective inhibitors of β-lactamases.MORANDI, S.; MORANDI, F.; CASELLI, E.; SHOICHET,B. K.; PRATI, F.
PL
R1BO
O
R1
BO
O
Cl
R1
BHO
OH
NHR2
OLiCHCl2 1) LiN(TMS)2
2) R2COCl
3) HCl
Bioorg. Med. Chem. 1195 12052008 16 -, , 3 ,
Transition Metal Catalyzed Hydroboration B
FRITSCHI, C. B.; WERNITZ, S. M.; VOGELS, C. M.; SHAVER, M. P.; DECKEN, A.; BELL, A.; WESTCOTT, S. A.
CC
OB
OH
PhPhPhPh
BO
OPh
PhPhPh
Rh(acac)(dppb) or [Cp*IrCl2]2
(1 eq), tolueneRhIr
Eur. J. Inorg. Chem. 779 7852008 -, , 5 ,
Novel Fluorine-Boron Complexes: Photoluminescence and Electrochemistry PropertiesB
ZHOU, Y.; XIAO Y.; LI, D.; FU, M.; QIAN, X.
MMA
NN
BF F
O
NN
BF F
O
J. Org. Chem. 1571 15742008 73 -, , 4 ,
Isomeric Boron-Fluorine Complexes with Donor-Acceptor ArchitectureB
Fluorescence of compounds 1 and 2 was compared to BODIPYs’ one in solution and solid state
ZHOU, Y.; XIAO Y.; QIAN, X.
MMA
N
O
O
NO
BF F
N
O
OB
F F
NO
1 2
Org. Lett. 633 6362008 10 -, , 4 ,
78
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Differentially Protected Benzenediboronic Acids in Synthesis of Oligoarene Boronic AcidsB
NOGUCHI, Y.; SHIODA, T.; CHOU, T-M.; SOGINOME, M.
MMA
B(OR)2
B(dan)
HNBHN
B(dan)=
R
R
X
R
X X
X
R
B(OH)2B(OH)2
Couplingand 5N HCl
Couplingand 5N HCl
B(OH)2
(HO)2B
Org. Lett. 377 3802008 10 -, , 3 ,
Catalytic Enantioselective Borane Reduction .B
HOBUD, D.; BARO, A.; LASCHAT, S.; FREY, W.
FV
Yields = 98 - 100%ee = 2 - 98%
Ph R
O
Ph R
OHBH3.THF, THF, 0°C
NO
OMe
R1A A =
R = Me, Et, iPr, CH2ClR1 = H, iPr, Bn
Tetrahedron 1635 16402008 64 -, , 8 ,
Stereocontrolled synthesis of αααα-methylene-γγγγ-lactones and lactams.B
Easy and rapid access to chiral α-methylene-γ-lactones and lactams via addition of allylboronates.CHATAIGNER, I.; ZAMMATTIO, F.. LEBRETON, J.; VILLIERAS, J.
FV
NR5
O
R2R3
R4 OO
R3R2
R4
BCOOR1
R2 R3
OH
R4
NH
R4
R5
ee = 6 - 82% with achiral aldehydeee = 30 - >95% with chiral aldehyde
ee = up to 95%
Tetrahedron 2441 24552008 64 -, , 10 ,
Borole Derivates as Radical Reactions Initiators.B
A initiates various radical reactions under mild conditions.
MONTGOMERY, I.; PARSONS, A.; GHEL, F.; RONCAGLIA, F.
FV
C6H13 + OB
OC3H7 A
C6H13P(O)(OEt)2HP(O)(OEt)2
RT, O2
A is commercialy available
Tetrahedron Lett. 628 6302008 49 -, , 4 ,
79
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Facile Reduction of Malonate Derivatives Using NaBH4/Br 2B
Efficient reduction of esters, acids, amides and malonate derivatives is presented.
TUDGE, M.; MASHIMA, H.; SAVARIN, C.; HUMPHREY, G.; DAVIES, I.
FV
Yields = 82-98%
R4O2C CO2R3
R R1 R R1OHHONaBH4 / Br2
Tetrahedron Lett. 1041 10442008 49 -, , 6 ,
Wittig Reaction of Formyl-Substituted Organotrifluo roborates.B
MOLANDER, G.; OLIVEIRA, R.
FV
Yields = 62- 85%E/Z = 51/49 - 100/0%
KF3B Ar CHO PPh3 RH2O, 90°C, 12h Ar
RBF3K
R =O
CH3
+
O
OMe
O
N CN, ,,
Ar = 6 substrates
Tetrahedron Lett. 1266 12682007 49 -, , 7 ,
Synthesis of ββββ-Lactones Assisted by Aluminum Bissulfonamide ComplexesAl
KULL, T.; PETER, R.
AF
O
BrMe
O
H R
AlR3 (15 mol %)EtN(i-Pr)2
toluene- 85 °C
OO
R
74 - 98 %78 - 90 % ee
+
HN HNArO2S SO2Ar
/ Dibal
for α-unbranched aldehyde
82 - 93 %84 - 88 % ee
PhPh
NH HNArO2S SO2Ar
for α-branched aldehyde
/ AlEt3*
Adv. Synth. Catal. 1647 16522007 349 -, , 10 ,
Highly Selective Method to Prepare 1,6-Diols Bearing Enyne Functions In
KIM, S.; LEE, K.; SEOMOON, D.; LEE, P.H.
AF
O
R2R1Br
Br In (1.1 equiv)LiI (1.1 equiv)
THF25 °C, 0.25 - 34 h 67 - 95 %
+ R2
OHR1
R2
HO R1
21 ex
Adv. Synth. Catal. 2449 24532007 349 -, , 10 ,
80
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Aluminum-Catalyzed Sulfur Oxidation by Al(salalen) ComplexesAl
MATSUMOTO, K.; YAMAGUCHI, T.; FUJISAKI, J.; SAITO, B.; KATSUKI, T.
PG
R1 SR2 R1 S
R2
OAl(salalen) (2 mol%)30% H2O2 (1.1 equiv)
MeOH, rt, 24 h
Al(salalen) (2 mol%)30% H2O2 (1.1 equiv)
MeOH, 10°C, 24 h
S S
Ph
S S
Ph
O
86% yield, 98% ee
10 examples80-86% yield80-99% ee
Chem. Asian J. 351 3582008 3 -, , 2 ,
Gas-Phase Lewis Acidity of Perfluoroaryl Derivatives of Group 13 ElementsAl
Structural data are described.
TIMOSHKIN, A. Y.; FRENKING, G.
LS
Ttheoretical studies of : E(C6H5)3, E(C6H4F)3, E(C5F5)3 E = B, Al, Ga
BGaZr
Organometallics 371 3802008 27 -, , 3 ,
Organoaluminium Hydroxydes Supported by ββββ-Diketiminato LigandsAl
Structural data are described.
YANG, Y.; SCHULTZ, T.; JOHN, M.; YANG, Z.; JIMENEZ-PEREZ, V. M.; ROESKY, H. W.; GURUBASAVARAJ, P. M.;STALKE, D.; YE, H.
LS
O
:C, H2O
-[H:C]+Cl-
NC
N
Cp2ZrMe2
-CH4Zr
Me:
:C =
L1 : R = Me ; Ar = 2,4,6-Me3C6H2
L2 : R = Me ; Ar = 2,6-iPr2C6H3
L3 : R = tBu ; Ar = 2,6-iPr2C6H3N
NH
R
R
Ar
Ar
LAlR
ClLAl
R
OH
LAlRZr
Organometallics 769 7772008 27 -, , 4 ,
Stereoselective Allylation of Sulfur- or Fluoro- Substituted TetrahydrooxepinsSi
A mechanism is proposed.
KOBAYASHI, S.; HORI, M.; HIRAMA, M.
LS
O
O
H
OTBS
SPhH
H H Methatesis (Grubbs II)
O
O
H
OR
R'H
H HSiMe3
Lewis acid
CH2Cl2O
O
H
ORH H
+ diastereoisomerR = TBS, Piv, H
R' = SPh, S(O)Ph, SO2Ph, F Yield : 30 - 92%Ratio (1:2) : 95:5 to 16:84
(1)
(2)
H
Ru
Carbohyd. Res. 443 4522008 343 -, , ,
81
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
From a Silabenzene to the Corresponding Anion Radical SpeciesSi
The reduction potential of silabenzene is lower than that of naphthalene
MATSUMOTO, T.; SASAMORI, T.; SATO, K.; TAKUI, T.; TOKITOH, N.
EJ
. -Si
Tbt
DME/rt
LiNpSi
Tbt
M
SiTbt
CH2Ph
OH
PhCH2Cl
water
Tbt = 2,4,6-tri(bisyl)phenyl;
(bisyl = (Me3Si)2CH)
M = Li(DME)n
+
48%
Li
Organometallics 305 3082008 27 -, , 3 ,
Reduction of Silabenzene Leading to the Corresponding Anion RadicalSi
ESR spectroscopy
MATSUMOTO, T.; SASAMORI, T.; SATO, K.; TAKUI, T.; TOKITHO, N.
LS
Si
R
LiNp
DME, rt
Si
R
M+ + Si
Me3Si SiMe3
Dis
Dis
Li(dme)
M = [Li(dme)n]
Dis = -CH(SiMe3)2
R = Tbt, H, Dmp
33%
Li
Organometallics 305 3072008 27 -, , 3 ,
Germanium and Tin Tetrafluoride Complexes with Thioether CoordinationGe
No adduct with GeCl4 which shows that GeF4 is a better Lewis acid even towards soft donor ligands
DAVIES, M.F.; LEVASON, W.; REID, G.; WEBSTER, M.; ZHANG, W.
EJ
F4M(CH3CN)2
RS(CH2)2SRR = Me, Et, iPr
M = Ge, Sn
CH2Cl2/rtF4M[RS(CH2)2SR]
60-69%
Dalton Trans 533 5382008 -, , 4 ,
Triphenylmetal 14 coordination compounds (Metal 14 = Germanium, Tin, Lead)Ge
With Lewis bases (Ph3PO, DMSO, pyridine), 1 gives hexacoordinated compounds
PENA-HUESCO, A.; ESPARZA-RUIZ, A.; RAMOS-GARCIA, I.; FLORES-PARRA, A.; CONTRERAS, R.
EJ
N
N
H
NH2
DMF/KOH/CS2
CHCl3 N
NN
SS
SK
N
NN
SS
S
MPh3
Ph3MCl
THF
135% 67-84%
M = Ge, Sn, Pb
SnPb
J. Organomet. Chem. 492 5042008 693 -, , 3 ,
82
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Theoretical Studies on the Imine Germylenoid HN=Ge(Na)FGe
TAN, X.; WANG, W.; LI, P.; WANG, Q.; ZHENG, G.; LIU, F.
EJ
Studies of geometries and isomerization of
the imine germylenoid HN=Ge(Na)F and its reaction insertion with RH
(R = F, OH, NH2, CH3)
Na
J. Organomet. Chem. 475 4822008 693 -, , 3 ,
Allylation of Ketones with a Ferrocene-Based Planar Chiral Lewis AcidSn
BOSHRA, R.; DOSHI, A.; JÄKLE, F.
LGE
FeO
R2R1
OH
R1Allyl R2
up to 80% ee
B
Sn
MeAllyl
Me
MeX+
X = Cl, Allyl
FeB
Angew. Chem. Int. Ed. 1134 11372008 47 -, , 6 ,
Inversion of the Usual Regioselectivity of the Aliphatic Retro-BrookSn
MORI, Y.; FUTAMURA, Y.; HORISAKI, K.
LGE
Me SnBu3
R31SiO OSiR3
2 n-BuLi
Me SiR31
OH OSiR32
Me SnBu3
R31SiO OSiR3
2
Me SiR31
OH OSiR32
n-BuLi
Si
Angew. Chem. Int. Ed. 1091 10932008 47 -, , 6 ,
Organotin(IV) Derivatives Containing 2-(Me2NCH2)C6H4 MoitiesSn
X-ray crystal structures andbehaviour in solution of the new organotins 1 and 2 are thoroughly reported.
VARGA, R.A.; JURKSCHAT, K.; SILVESTRU, C.
TT
NMe2
SnS
SSn
Bu
N Me
Me
Bu
N
Me
Me
i) BuLiii) BuSnCl3
RBuSnCl2
R2SnCl2
Na2S (excess)
1
2
R = 2-(Me2NCH2)C6H4
Eur. J. Inorg. Chem. 708 7162008 -, , 5 ,
83
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Benzothiazines in Synthesis: Studies Directed toward the Synthesis of ErogorgiaeneSn
HARMATA, M.; HONG, X.; SCHREINER, P. R.
BI
CO2Me
N
CHO
BrS Ph
O
62% yield (3 steps)
I
CO2Et
Me
37% (6 steps)
Bu3SnH (1.6eq)
AIBN (0.14eq)C6H6, reflux, 12h
CO2Et
Me
H
96%cis/trans = 7.4/1
J. Org. Chem. 1290 12962008 73 -, , 4 ,
Novel Diastereoselective Synthesis of Bicyclic ββββ-LactamsSn
The reductive ring opening of these bicyclic β-lactams resulted in novel piperidine and azepane compounds.
LEEMANS, E.; D’HOOGHE, M.; DEJAEGHER, Y.; TÖRNROOS, K. W.; De KIMPE, N.
BI
N
R1O
O
R3
R2
Br
Bu3SnH
AIBN, tolueneN
R1O
ON
R1O
O
HH
R2
Bu3SnH
AIBN, toluene
R2 = H ; R3 = Me R2 = H,Ph ; R3 = H
R1 = Me, Ph, Bn
16-21%(de = 75-78% in favor of the trans isomer)
28-37%(one diastereoisomer)
J. Org. Chem. 1422 14282008 73 -, , 4 ,
Unprecedented Negishi Coupling at C-Br in Presence of a Stannyl GroupSn
Materials = pyridine-thiophene-pyridine ; (thioph.-pyr)2-thioph. ; terpyr. ; thioph.-bipyr. ; thioph.-pyr.-thioph. ...
GETMANENKO, Y. A.; TWIEG, R. J.
BI
N
Br
Br
1) i-PrMgCl, rt
2) Bu3SnCl, rt
90%
N
Br
SnBu3
R-ZnCl, rtPd(PPh3)4
57-77%
N
R
SnBu3
Ar-BrPd(PPh3)4
41-70%
N
R
Ar
Liquid crystalline materials
MgZnPd
J. Org. Chem. 830 8392008 73 -, , 3 ,
Supramolecular Catalysis at Work: Diastereoselective Synthesis of a Molecular Bowl Sn
YAN, Z.; McCRACKEN, T.; XIA, S.; MASLAK, V.; GALLUCCI, J.; HADAD, C. M.; BADJIC, J. D.
BI
Br
Me3SnN
N Pd(PPh3)4, Cu(I) (20%)
CsF (2 mol. eq)CsClO4 (8 mol. eq) N
N
N
N
N
N
24% yield ; syn/anti = 4.5 : 1
41% overall yield (4 steps)
CuPd
J. Org. Chem. 355 3632008 73 -, , 2 ,
84
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
A Multicomponent Synthesis of ImidazolonesSn
SIAMAKI, A. R.; BLACK, D. A.; ARNDTSEN, B. A.
BI
R2 H
NR1
Cl OR3
O
R4 SnBu3+ + + CO
1) 5% Pd2dba3 Bu4NBr, rt, 24-48h CH2Cl2/CH3CN
2) NH4OAc, AcOH reflux, 12-16h
NHN
O
R4 R2
R1
60-86%
Pd
J. Org. Chem. 1135 11382008 73 -, , 3 ,
Stereoselective Total Synthesis of (-)-Perrottetinene Sn
With other protecting groups than Bz, the Stille coupling was very sluggish.
SONG, Y.; HWANG, S.; GONG, P.; KIM, D.; KIM, S.
BI
OBz
I
OBzBn
+Bu3Sn
OHPd2(dba)3, P(t-Bu)3
CuI, CsFToluene, 80°C, 5h
OBz
OBzBn
OH
78%
O
BnOH
nine steps - 15% overall
Pd
Org. Lett. 269 2712008 10 -, , 2 ,
Spurring Radical Reactions of RX with Bu3SnH or TTMSS Using MicroreactorsSn
The reaction works with a continuous system.
FUKUYAMA, T.; KOBAYASHI, M.; RAHMAN, Md. T.; KAMATA, N.; RYU, I.
BI
Bu3SnH (1.2eq)radical initiator (2-10mol%)RX - toluene (0.05 to 0.4 M)
80°C-130°Cresidence time = 1-15 min
Microreactor
R-H
> 92%
radical initiator
N NR'
R' R' = MeO-CMe2CH2CMe(CN)- iPrCH2-CMe(CN)- Me2C(CN)-
CN
Org. Lett. 533 5362008 10 -, , 4 ,
Sequential Rh(I)/Pd-Catalyzed 1,4-Addition/Intramolecular AllylationSn
FILLION, E.; CARRET, S.; MERCIER, L. G.; TRÉPANIER, V. É.
BI
O O
O O
X
X = Me, Ph, Ar
Bu3Sn OR1
[RhCl(cod)]2(3mol% Rh)THF, rt, 2-20h
O O
O O
XOR1
R1 = Ac, CO2Et
70-91% yield
[Pd], THF/R2OH
6-15h O
O
Ph
O
R2O60-87%
Pd(II) 10mol%Yb(OTf)3 20mol%
THF, rt, 24h
with R1=Ac
O O
O O
Ar
68-71%
R2=H, Me, Et
RhPd
Org. Lett. 437 4402008 10 -, , 3 ,
85
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Stereoselective Synthesis of Substituted Tetrahydrofurans and TetrahydrooxepinesSn
The solvent changes the outcome of the reaction and the reaction proceeds with a retention of stereochemistry.
KIM, S.-H.; OH, S.-J.; HO, P.-S.; KANG, S.-C.; O, K.-J.; YU, C.-M.
BI
R1
OTMS
i) (Me3Sn)2, (π-allyl)2Pd2Cl2 (0.5mol%)
ii) TMSOTf, R2CHO
-78°C, THF
ii) TMSOTf, R2CHO
-40°C, CH2Cl2OR1R2
H H
SnMe3
53-87%up to > 99:1
OR1 R2
H H
61-80%up to > 99:1
R1 = Ph, alk
R2 = alkyl
Pd
Org. Lett. 265 2682008 10 -, , 2 ,
Total Synthesis of Stemonamide and Isostemonamide Using Radical CascadeSn
TANIGUCHI, T.; TANABE, G.; MURAOKA, O.; ISHIBASHI, H.
BI
O
NO
Br
Bu3SnHACN
toluene, refluxNO
O
**
55% yield2 diastereoisomers (1:1)
NO
OO
O
MeO
stemonamide
Org. Lett. 197 1992008 10 -, , 2 ,
A Polystyrene-Supported Tin Trichloride Catalyst with a C11-SpacerSn
HRMAS NMR and modulated DSC have evidenced the chemical integrity of the catalyst upon recycling.
PINOIE, V.; POELMANS, K.; MILTNER, H.E.; VERBRUGGEN, I.; BIESEMANS, M.; VAN ASSCHE, G.; VAN MELE, B.;MARTINS, J.C.; WILLEM, R.
TT
O
OEt
P (CH2)11SnCl3 O
OC8H17
+ C8H17OH + EtOH
conversion yield = 76% after 2h recycling ability > 9 cyclestin residues : 5 ppm
Organometallics 6718 67252007 26 -, , 27 ,
Allylation of Aldehydes Activated by MgI2.(OEt)n with AllyltributylstannaneSn
ZHANG, X.
LGE
O
HRSnBu3+
MgI2.(OEt2)n
R
OH
CH2Cl2, rt67 - 97%
R = Aromatic, Vinyl, Alkyl
Mg
Synlett 65 682008 -, , 1 ,
86
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Highly Efficient Catalysts for Allylation of Aldehy des with AllyltributyltinSn
ZHANG, T.; SHI, M.; ZHAO, M.
BE
R'CHO + SnBu3Bis(NHC)-Pd(II) Complex
THF, Ar, rtR'
OH
yields = 46 to 99%
N
N
N
N
CH3
CH3
PdOCOR
OCOR
R = Me, CF3
Pd
Tetrahedron 2412 24182008 10 -, , 64 ,
C–C Coupling of Bismuth(V) Derivatives and Olefins in Presence of Pd Nanoparticles.Bi
This base-free Heck reaction proceeds with very low Pd loading.
MALYSHEVA, Y. B.; GUSHCHIN, A. V.; MEI, Y.; LU, Y.; BALLAUFF, M.; PROCH, S.; KEMPE, R.
GR
Bi(Ph)3(X)2R
+R
Ph
X= alkoxide, carboxylateR= Ph, CO2Et, CO2nBr, C(O)NH2
supported Pdnanoparticles
(0.04 mol% Pd)poor to good yield
Pd
Eur. J. Inorg. Chem. 379 3832008 -, , 3 ,
A New Methodology for Synthesis of Aryl Bismuth CompoundsBi
STAVILA, V.; THURSTON, J.H.; PRIETO-CENTURION, D.; WHITMIRE, K.H.
AN
RNaB4Bi(O2CR')3 RBi
3
R = H, F, Me
Organometallics 6864 68662007 26 -, , 27 ,
Polychromophoric metal complexes for generating nitric oxydeRv
FORD P.C.
GN
> 54 references
Design of photoactive metal complexes for controlled release of NO
FeCr
Acc. Chem. Res. 190 2002008 41 -, , 2 ,
87
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Transition Metal Pincer Complexes Based on AminophosphinesRv
Synthesis and catalytic applications of pincer complexes
BENITO-GARAGORRI D.; KIRCHNER K.
GN
> 31 references
Y
NH
HNR'
M
PR2
PR2
Ln
MoFeRuNiPdPt
Acc. Chem. Res. 201 2132008 41 -, , 2 ,
C-H and C-C Bond Activation using Metal-organic Cooperative CatalysisRv
PARK Y.J.; PARK J.-W.; JUN C.-H.
GN
> 41 references
RhRu
Acc. Chem. Res. 222 2342008 41 -, , 2 ,
Cross-coupling Methodologies through Intermediates MetalacyclesRv
JOHNSON J.B.; ROVIS T.
GN
> 46 references
Nucleophilic interception of metalacycles for the stereocontrolled formation of carbon-carbon bonds in cross-coupling of anhydrides with organozinc reagents
ZnNiPd
Rh
Acc. Chem. Res. 327 3382008 41 -, , 2 ,
The Role and Influence of Olefins in Cross-Coupling ReactionsRv
JOHNSON, J. B.; ROVIS, T.
CY
203 references
PtPdCuNiZrZn
Angew. Chem. Int. Ed. 840 8712008 47 -, , 5 ,
88
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Metal Vinylidenes as Catalytic Species in Organic Chemistry: Reactions and ApplicationsRv
TROST, B. M.; MCCLORY, A.
PG
Review (>126 references)
Chem. Asian J. 164 1942008 3 -, , 2 ,
Sustainable Chemistry: Immobilized Metal Catalysts for Alcohols OxidationRv
MATSUMOTO, T.; UENO, M.; WANG, N.; KOBAYASHI, S.
PG
Review (>150 references)
Chem. Asian J. 196 2142008 3 -, , 2 ,
1,5-Asymmetric Induction in Boron-Mediated Aldol ReactionsRv
A tutorial review with 55 references
DIAS, L. C.; AGUILAR, A. M.
MVI
O
MeR1
OR' R2B-X OBR2
R1
OR' H
O
O
R1
OR' OH
1,5-anti
Chem. Soc. Rev. 451 4692008 37 -, , 3 ,
Recent Advances in Organothorium and Organouranium CatalysisRv
A critical review with 118 references
ANDREA, A.; EISEN, M. S.
MVI
- Hydroamination- Hydrosilylation of terminal alkynes- Coupling of terminal alkynes with isonitriles
- Catalytic reduction of azides and hydrazines- Ring opening polymerization of cyclic esters- Polymerization of α-olefins
Chem. Soc. Rev. 550 5672008 37 -, , 3 ,
89
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Functionalization of Diazines and Benzodiazines through Deprotonated IntermediatesRv
A critical review with ca. 70 references
CHEVALLIER, F.; MONGIN, F.
MVI
NN
H
R
NN
M
R
NN
El
R
Chem. Soc. Rev. 595 6092008 37 -, , 3 ,
Photosystem II.Rv
BRUDVIG, G. W. AS COORDINATOR.
MJ
CO2 + H2OPhotosynthesis
[Mn4Ca](CH2O) + O2
fossilefuels
added toatmosphere
16 reviews about the following topic:
Coordin. Chem. Rev. 231 4682008 252 -, , 3-4,
Luminescent Complexes with Polypyridyl-Functionnalized Alkynyl LigandsRv
A perspective
CHEN, Z.-N.; FAN, Y.; NI, J.
MVI
N N[M][M]
[M']
Dalton Trans 573 5812008 -, , 5 ,
Chemistry of Aluminium (I), Silicon (II) and German ium (II)Rv
The same chemistry with Si(II) and Ge(II) is reported.
NAGENDRAN, S.; ROESKY, H. W.
LS
NAl
NAr
Ar
Synthesis of a monomeric Al(I) derivative LAl and its reactivity with alkynes, azydes,oxygen, sulfur, phosphorus...176 references.
AlSiGe
Organometallics 457 4922008 27 -, , 4 ,
90
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
Lewis Acidic Properties of Fluorinated OrganomercurialsRv
Synthesis, structure and properties of neutral Lewis adducts involving fluorinated organomercurials
TAYLOR, T.J.; BURRESS, C.N.; GABBAI, F.P.
PB
REVIEW
Hg
Organometallics 5252 52632007 26 -, , 22 ,
Metal-catalyzed Functionalization of Phthalocyanines and Subphthalocyanines.Rv
MARTINEZ-DIAZ, M. V.; QUINTILIANI, M.; TORRES, T.
MJ
Use of various transition metals>43 references
Synlett 1 202008 -, , 1 ,
Organic Synthesis using Microflow Systems.Rv
FUKUYAMA, T.; RAHMAN, M. T.; SATO, M.; RYU, I.
MJ
Various metal-catalyzed reactions (Heck, Sonogashira, carbonylation, ...)some of them being carried out in ionic liquids.
> 47 references.
Pd
Synlett 151 1632008 -, , 2 ,
Is Osmylation Always Preferring the Richest Double Bond?Rv
Focused on various alkene dihydroxylations (achiral and chiral) by AD-mix reagents
FRANÇAIS, A.; BEDEL, O.; HAUDRECHY, A.
CM
MeO2C OPMB
O
O
MeO2C OPMB
O
O
OH
OH
AD-mix α
tBuOH/acetone/H2O
Os
Tetrahedron 2495 25242008 64 -, , 11 ,
91
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 2)
“On-Off” Fluorescent Chemosensor for Cu2+Rv
KIM, H. J.; PARK, S. Y.; YOON, S.; KIM, J. S.
LE
NH
O
N
OO
OO
Cu2+
Tetrahedron 1294 13002008 64 -, , 7 ,
92
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