Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using α-(phenylthio)isobutyrophenone

Mieko Arisawa, Fumihiko Toriyama, Masahiko Yamaguchi

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

In the presence of catalytic amounts of RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-benzothiazoles, 1,3-benzoxazoles, and benzothiophene reacted with α-(phenylthio) isobutyrophenone giving 2-phenylthio derivatives. Reactive monocyclic heteroaromatics, 1-methyl-1,2,3,4-tetrazole and 2-cyanothiophene were also converted into the 5-phenylthio derivatives. The use of an appropriate phenylthio transfer reagent is crucial for the efficient catalyzed conversion of heteroaromatic C-H bonds into C-S bonds.

Original languageEnglish
Pages (from-to)2344-2347
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number18
DOIs
Publication statusPublished - 2011 May 4

Keywords

  • Benzothiazole
  • C-H activation
  • Equilibrium
  • Heteroaromatics
  • Phenylthiolation
  • Rhodium catalyst

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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