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

Silvia Diez-Gonzalez, Andrea Correa, Luigi Cavallo, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

319 Citations (Scopus)

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 excellent 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 cycloaddition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic pathway for disubstituted alkynes.

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

Keywords

  • alkynes
  • azides
  • click chemistry
  • copper N-heterocyclic carbenes
  • COPPER(I)-CATALYZED 3-COMPONENT REACTION
  • HETEROCYCLIC CARBENE COMPLEXES
  • 1,3-DIPOLAR CYCLOADDITION
  • TERMINAL ALKYNES
  • CLICK-CHEMISTRY
  • 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES
  • CATALYZED CYCLOADDITION
  • TRIMETHYLSILYL AZIDE
  • SOLID-PHASE
  • WATER

Fingerprint

Dive into the research topics of '(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes'. Together they form a unique fingerprint.

Cite this