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

Ryuki Kakino, Sayaka Yasumi, Isao Shimizu, Akio Yamamoto

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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
Issue number1
Publication statusPublished - 2002 Jan


ASJC Scopus subject areas

  • Chemistry(all)

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