Synthesis of enaminones by rhodium-catalyzed denitrogenative rearrangement of 1-(N -Sulfonyl-1,2,3-triazol-4-yl)alkanols

Tomoya Miura, Yuuta Funakoshi, Masao Morimoto, Tsuneaki Biyajima, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

138 Citations (Scopus)

Abstract

Enaminones are synthesized by the rhodium(II)-catalyzed denitrogenative rearrangement reaction of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols, which are readily prepared from propargylic alcohols and N-sulfonyl azides. Intramolecular 1,2-hydride (or -alkyl) migration occurs with an intermediary α-imino rhodium(II) carbenoid species generated through denitrogenation of the 1,2,3-triazol-4-yl moiety. The resulting enaminones is converted into various heterocycles with replacement of the N-sulfonyl group.

Original languageEnglish
Pages (from-to)17440-17443
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number42
DOIs
Publication statusPublished - Oct 24 2012
Externally publishedYes

ASJC Scopus subject areas

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

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