(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and Mono- Or disubstituted alkynes

Silvia Díez-González, Andrea Correa, Luigi Cavallo, Steven P. Nolan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

311 Scopus citations

Abstract

A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N-heterocyclic carbene). Extremely high reaction rates and excel lent yields were obtained in all cases. This catalytic system fulfils the requirements of "click chemistry" with its mild and convenient conditions, nota bly in water or solvent free reactions and simple isolation with no purification step. Furthermore, for the first time, an internal alkyne was successfully used in this copper-catalyzed cyclo-addition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic path-way for disubstituted alkynes.

Original languageEnglish (US)
Pages (from-to)7558-7564
Number of pages7
JournalChemistry - A European Journal
Volume12
Issue number29
DOIs
StatePublished - Oct 10 2006

Keywords

  • Alkynes
  • Azides
  • Click chemistry
  • Copper
  • N-heterocyclic carbenes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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