Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes

Stepan Chuprakov, Sen Wai Kwok, Valery V. Fokin

Research output: Contribution to journalArticle

162 Citations (Scopus)

Abstract

Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.

Original languageEnglish
Pages (from-to)4652-4655
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number12
DOIs
Publication statusPublished - 27 Mar 2013
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

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