A Reaction of Triazoles with Thioesters to Produce β-Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur-Carbonyl Bond

Tomoya Miura, Yoshikazu Fujimoto, Yuuta Funakoshi, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

76 Citations (Scopus)

Abstract

N-Sulfonyl-1,2,3-triazoles react with thioesters in the presence of a rhodium(II) catalyst to produce β-sulfanyl enamides in a stereoselective manner. The reaction proceeds through generation of an α-imino rhodium carbene complex, nucleophilic addition of the sulfur atom of a thioester onto the carbenoid carbon atom, and subsequent intramolecular migration of the acyl group from the sulfur atom to the imino nitrogen atom. The method is successfully applied to a ring-expansion reaction of thiolactones, thus leading to the formation of sulfur-containing lactams.

Original languageEnglish
Pages (from-to)9967-9970
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number34
DOIs
Publication statusPublished - Aug 1 2015
Externally publishedYes

Keywords

  • carbenoids
  • copper
  • heterocycles
  • rhodium
  • sulfur

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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