Post on 18-Dec-2015
OutlineIntroductionChemistry of Suzuki ReactionReaction mechanismBoron reagents
Recent development of Suzuki ReactionConjugated microporous polymersLight-emitting diodesOrganic Solar cell
Polymer-bound palladium catalyst in Suzuki Reaction
Conclusions2
IntroductionThe Suzuki reaction is the organic reaction that is
classified as a coupling reaction where the coupling partners are a boronic acid with a halide catalyzed by a palladium(0) complex
It was first published in 1979 by Akira Suzuki and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their effort for discovery and development of palladium-catalyzed cross couplings in organic synthesis.
3Richard F. Heck Akira SuzukiEi-ichi Negishi
4
Suzuki Reaction and Stille Reaction
Ar: the relative reactivity appears to be PhI >p-ClC,H,Br > PhBr > o-MeC,H,Br > o-MeOC,H,Br.
A. Suzuki, Chem. Commun. 1979, 866.
Stille Reaction
J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508
R1 Sn(Alkyl)3 + R2 XPd0(catalytic)Lidand Set
R1 R2 X Sn(Alkyl)
R1, R2 =sp2 hybridized C(allyl, alkenyl, aryl); X=halides(Cl, Br, I), pseudohalides(OTf, OSO2CF3, OPO(OR)2)
+
OutlineIntroductionChemistry of Suzuki ReactionReaction mechanismBoron reagents
Recent development of Suzuki ReactionConjugated microporous polymersLight-emitting diodesOrganic Solar cell
Polymer-bound palladium catalyst in Suzuki Reaction
Conclusions5
OutlineIntroductionChemistry of Suzuki ReactionReaction mechanismBoron reagents
Recent development of Suzuki ReactionConjugated microporous polymers Organic light-emitting diodesOrganic Solar cell
Polymer-bound palladium catalyst in Suzuki Reaction
Conclusions9
Conjugated microporous polymers
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A. I. Cooper, et al, Angew. Chem., Int. Ed., 2012, 51, 12727–12731.
Subi J. George, et al, J. Mater. Chem., 2011, 21, 12958
Han, B.-H., et al, Macromolecules, 2011, 44, 5573.
Organic light-emitting diodes
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T. Yokozawa, et al, J. AM. CHEM. SOC. 2007, 129, 7236
Polyfluorene
Polyfluorenes are an important class of polymers which have the potential to act as both electroactive and photoactive materials.
OutlineIntroductionChemistry of Suzuki ReactionReaction mechanismBoron reagents
Recent development of Suzuki ReactionConjugated microporous polymersLight-emitting diodesOrganic Solar cell
Polymer-bound palladium catalyst in Suzuki Reaction
Conclusions14
Polymer-bound palladium catalyst
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C. Le Drian, et al, Tetrahedron Lett. 1998, 39, 4287
W.-C. Shieh, et al, Synth. Commun. 2002, 32, 1059.
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SCHEME 1. Schematic Representation of Magnetic Nanoparticle Facilitated Solid-Phase Suzuki Cross Coupling Reactions
SCHEME 2. Immobilization of Pd-NHC Complexes ontothe Surface of Iron Oxide Nanoparticles
Gao, Y. J. Org. Chem.2006, 71, 537.
OutlineIntroductionChemistry of Suzuki ReactionReaction mechanismBoron reagents
Recent development of Suzuki ReactionConjugated microporous polymersLight-emitting diodesOrganic Solar cell
Polymer-bound palladium catalyst in Suzuki Reaction
Conclusions18