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

Ryuki Kakino, Sayaka Yasumi, Isao Shimizu, Akio Yamamoto

Research output: Contribution to journalArticle

119 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)137-148
Number of pages12
JournalBulletin of the Chemical Society of Japan
Volume75
Issue number1
DOIs
Publication statusPublished - 2002 Jan

ASJC Scopus subject areas

  • Chemistry(all)

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