Pd(II)-bipyridine catalyzed conjugate addition of arylboronic acid to alpha,beta-unsaturated carbonyl compounds

Xiyan Lu; Shaohui Lin

doi:10.1021/jo051561h

Pd(II)-bipyridine catalyzed conjugate addition of arylboronic acid to alpha,beta-unsaturated carbonyl compounds

J Org Chem. 2005 Nov 11;70(23):9651-3. doi: 10.1021/jo051561h.

Authors

Xiyan Lu¹, Shaohui Lin

Affiliation

¹ 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

PMID: 16268654
DOI: 10.1021/jo051561h

Abstract

[Reaction: see text]. A Pd(II)-catalyzed conjugate addition of arylboronic acid to alpha,beta-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 beta-hydride elimination.