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Synfacts 2014; 10(1): 0102
DOI: 10.1055/s-0033-1340401
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

A Heterogeneous Bifunctional Au/Pd Nanoparticle Organocatalyst

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Takuma Sato
Miyamura H, Choo GC. Y, Yasukawa T, Yoo W.-J, Kobayashi S * The University of Tokyo, Japan
A Heterogeneous Layered Bifunctional Catalyst for the Integration of Aerobic Oxidation and Asymmetric C–C Bond Formation.

Chem. Commun. 2013;
49: 9917-9919
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

bifunctional catalysis - gold nanoparticles - palladium nanoparticles - organocatalysis - aerobic oxidation - asymmetric C–C bond formation

Significance

The preparation of a polymer-incarcerated Au/Pd-coated organocatalyst [PI(Au/Pd)-CO] for the sequential aerobic oxidation–Michael reaction between γ-substituted allylic alcohols and dibenzylmalonate was described. The reaction of 3-phenyl-2-propen-1-ol (1) and dibenzylmalonate (2) proceeded in the presence of PI(Au/Pd)-CO to give dibenzyl 2-(3-oxo-1-phenylpropyl)propanedioate (3) in 75% yield with 90% ee (other 9 examples: 34–83% yield, 74–91% ee).


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Comment

The Au/Pd organocatalyst was prepared by the copolymerization of monomers 5, 6 and 7 in the presence of V-601 [dimethyl 2,2′-azobis(2-methylpropionate)] as a radical initiator followed by the formation of the cross-linked shell layer of a polymer 9 in which bimetallic Au/Pd nanoparticles were incorporated. Thus, PI(Au/Pd)-CO was composed of an organocatalytic resin core and a polymeric Au/Pd nanoparticle shell.


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