Copper(I)-catalyzed cycloaddition of bismuth(III) acetylides with organic azides: Synthesis of stable triazole anion equivalents

Brady T. Worrell, Shelby P. Ellery, Valery V. Fokin

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Fully loaded: Readily accessible and shelf-stable 1-bismuth(III) acetylides react rapidly and regiospecifically with organic azides in the presence of a copper(I) catalyst (see scheme). The reaction tolerates many functional groups and gives excellent yields of the previously unreported 5-bismuth triazolides. This uniquely reactive intermediate is functionalized under mild reaction conditions to give fully substituted 1,2,3-triazoles.

Original languageEnglish
Pages (from-to)13037-13041
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number49
DOIs
Publication statusPublished - 2 Dec 2013
Externally publishedYes

Keywords

  • bismuth
  • click chemistry
  • copper
  • cycloaddition
  • heterocycles

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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