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

Stepan Chuprakov, Sen Wai Kwok, Valery V. Fokin

Research output: Contribution to journalArticle

159 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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Triazoles
Metals
Isothiocyanates
Isocyanates
Thiazoles
1-sulfonyl-1,2,3-triazole

ASJC Scopus subject areas

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

Cite this

Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes. / Chuprakov, Stepan; Kwok, Sen Wai; Fokin, Valery V.

In: Journal of the American Chemical Society, Vol. 135, No. 12, 27.03.2013, p. 4652-4655.

Research output: Contribution to journalArticle

Chuprakov, Stepan ; Kwok, Sen Wai ; Fokin, Valery V. / Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 12. pp. 4652-4655.
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