Organosulfur and Organoselenium Compounds in Catalysis...Organosulfur and Organoselenium Compounds...
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1643 Cover Page Cluster S. Huber N Ph H N Ph N N N N Ch Ch Oct Oct 2 OTf – without any activating agent and selected Lewis acids N COOEt EtOOC H H H H H 2 equivalents Hak-Fun Chow The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong Ying-Yeung Yeung The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong This Cluster provides insights into some of the most recent advances and aspects in the field of transformations catalyzed by organosulfur and organoselenium compounds. Enjoy eleven wonderful contributions by experts in this field! Syn lett X. Zhang Organosulfur and Organoselenium Compounds in Catalysis Ph Ph O OH H 2 O 2 OH Ph O up to 88% isolated yield scalable (at least 100 mmol) + H 2 O + MeCN, rt First example of pollutant degradation through Se catalysis 10 mol% PhSe(O)OH from (PhSe) 2 S. Shirakawa A. Tsuchihashi This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.
Transcript of Organosulfur and Organoselenium Compounds in Catalysis...Organosulfur and Organoselenium Compounds...
1643
Cover Page ClusterSyn lett
ly p
rohi
bite
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Hak-Fun ChowThe Chinese University of Hong Kong, Shatin, New Territories, Hong Kong
Ying-Yeung YeungThe Chinese University of Hong Kong, Shatin, New Territories, Hong Kong
This Cluster provides insights into some of the most recent advances and aspectsin the field of transformations catalyzed by organosulfur and organoseleniumcompounds. Enjoy eleven wonderful contributions by experts in this field!
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Una
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S. Huber
N PhHN Ph
N N
NNChCh
OctOct2 OTf–
without any activating agentand selected Lewis acids
N
COOEtEtOOC
HH
H
H
H
2 equivalents
X. Zhang
Organosulfur and Organoselenium Compounds in Catalysis
PhPh
O
OH
H2O2OHPh
O
up to 88% isolated yieldscalable (at least 100 mmol)
+ H2O+MeCN, rt
First example of pollutant degradation through Se catalysis
10 mol% PhSe(O)OHfrom (PhSe)2
S. ShirakawaA. Tsuchihashi
© Georg Thieme Verlag Stuttgart · New York — Synlett 2014, 25, 1707–1709
1644
© Georg Thieme Verlag Stuttgart · New York — Synlett 2014, 25, 1707–1709
Cover Page Cluster
H. Li L. Liao X. Zhao
R2R1 N
XH
R2R1 N
N
oxidant
X = NPG, O
catalyticPhSeSePh PG
Ph
NO
or
Syn lett
K. Robb S. Athavale S. Denmark
F
R
HO
N
P
NMe
Me
Se
N(i-Pr)2N
O
S
O i-Pr
i-Pr
sulfenylating agent
LB* catalyst
HFIP, 25 °C
Unusual kinetic behavior!
~0.5 order in substrate
~0.5 order in sulf. agent
1st order in catalyst
Rate unaffected by R
F
O
SH
R
i-Pr
i-Pr
R = OMe, H, Cl, CN
T. Hashimoto
OMeO
Se 2 Sit-Bu
Me Me
M.-H. Xu
O
O
O
HPh N
H
S
Ph O
[Rh], ArB(OH)2
ArOiPr
OH
O
70–99% yield, up to 83% ee
COOMeCl
N
SClopidogrel0.1 M KOH, dioxane
40 °C15 examples
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2014, 25, 1707–1709
Cover Page Cluster
A. Dinh A. Nguyen J. Gustafson
photocatalystNa2S2O8, base additive
MeCN–H2Oblue LED, 12 h, r.t.
NH
O NH
O
NH
S
+
SH
S
N
NH
O NH
O
S
S. D. MinteerL. Yu
Syn lett
L. Yu X. Jiang
S. Kumar S. Jana
SO
ON
H
O
N
N
O
O
O
N Pocket
C2-Symmetric Sulfur Based ChiralCatalyst for Bromolactonization T
his
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