Synthesis of unsymmetrical ketones by palladium-catalyzed cross-coupling reaction of carboxylic anhydrides with organoboron compounds

Ryuki Kakino, Sayaka Yasumi, Isao Shimizu, Akio Yamamoto*

*この研究の対応する著者

研究成果: Article査読

125 被引用数 (Scopus)

抄録

On the basis of fundamental studies on oxidative addition of carboxylic anhydrides to zerovalent palladium complexes to yield acyl(carboxylato)bis(tertiary phosphine)palladium(II) complexes and their reactions with organoboronic acids to yield ketones, a novel catalytic process has been developed. This converts carboxylic anhydrides and organoboron compounds into ketones catalyzed by palladium complexes under mild conditions. The process provides a general, versatile, synthetic method to produce various symmetrical and unsymmetrical ketones with aromatic, aliphatic, and heterocyclic groups. The catalytic cycle is proposed to comprise (a) oxidative addition of a carboxylic anhydride to produce an acyl(carboxylato)palladium intermediate, (b) transmetallation with an organoboron compound to give an acyl(organo)palladium intermediate, and (c) its reductive elimination to yield a ketone. Not only homogeneous catalyst systems but also heterogeneous systems were found to give ketones under mild conditions.

本文言語English
ページ(範囲)137-148
ページ数12
ジャーナルBulletin of the Chemical Society of Japan
75
1
DOI
出版ステータスPublished - 2002 1

ASJC Scopus subject areas

  • 化学 (全般)

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