Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters: Synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement

Mieko Arisawa, Manabu Kuwajima, Fumihiko Toriyama, Guangzhe Li, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

In the presence of catalytic amounts of RhH(CO)(PPh3) 3 and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of ketone CO-C bonds and intermolecular rearrangement giving unsymmetric ketones. The acyl-transfer reaction also occurred with 1-(p-chlorophenyl)-3-(p-cyanophenyl)propane-2-one giving unsymmetric ketones.

Original languageEnglish
Pages (from-to)3804-3807
Number of pages4
JournalOrganic letters
Volume14
Issue number14
DOIs
Publication statusPublished - 2012 Jul 20

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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