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Pd(II)-Bipyridine Catalyzed Conjugate Addition of Arylboronic Acid to α,β-Unsaturated Carbonyl Compounds

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Xiyan Lu* and Shaohui Lin

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China xylu@mail.sioc.ac.cn

J. Org. Chem., 2005, 70 (23), pp 9651–9653

DOI: 10.1021/jo051561h

Publication Date (Web): October 12, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

A Pd(II)-catalyzed conjugate addition of arylboronic acid to α,β-unsaturated ketones, aldehydes, esters, etc. in the presence of 2,2‘-bipyridine was developed. A mechanism involving transmetalation, insertion of the carbon−carbon double bond into the C−Pd bond, and protonolysis of the resulting C−Pd bond is proposed. The reaction conditions are mild and the yield is high. The presence of 2,2‘-bipyridine is crucial for the reaction to inhibit β-hydride elimination.

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Published In Issue November 11, 2005
Received July 26, 2005

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Pd(II)-Bipyridine Catalyzed Conjugate Addition of Arylboronic Acid to α,β-Unsaturated Carbonyl Compounds

Abstract

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Related Content

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