Rhodium-catalyzed methylthio transfer reaction between ketone α-positions: Reversible single-bond metathesis of C-S and C-H bonds

Mieko Arisawa, Katsunori Suwa, Masahiko Yamaguchi

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

(Chemical Equation Presented) In the presence of a catalytic amount of RhH(PPh3)4 and 1,2-bis(diphenylposphino)ethane (dppe), α-phenylthio ketones were methylthiolated with ρ-cyano-α- methylthioacetophenone giving α-phenylthio-α-methylthio ketones. The methylthio transfer reaction between the ketone α-positions was reversible and at equilibrium, and the methylthio group was transferred in preference to the phenylthio group. The reaction of tertiary alkyl methylthiomethyl ketones proceeded in high yields; the reaction of diastereomeric 4-(tert-butyl)-2-phenylthiocyclohexanones gave an axial 2-methylthiolated product.

Original languageEnglish
Pages (from-to)625-627
Number of pages3
JournalOrganic letters
Volume11
Issue number3
DOIs
Publication statusPublished - 2009 Feb 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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