Consecutive O−S/N−S Bond Cleavage in Gold-Catalyzed Rearrangement Reactions of Alkynyl N-Sulfinylimines

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Abstract

Gold-catalyzed reactions of alkynyl N-sulfinylimines were used to produce the corresponding 2H-azirines possessing sulfenyl and acyl groups at the 3-position of the azirine ring in good to excellent yields. These reactions involved internal transfer of the sulfinyl oxygen atom to form a thiooxime intermediate tethered to an α-oxo gold carbene moiety. Subsequent insertion of the carbene into the N−S bond resulted in ring construction.

Original languageEnglish
Pages (from-to)12248-12252
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number22
DOIs
Publication statusPublished - 2021 May 25

Keywords

  • alkynes
  • carbenes
  • gold
  • heterocycles
  • rearrangement

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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