Mechanism of the ligand-free CuI-catalyzed azide-alkyne cycloaddition reaction

Valentin O. Rodionov, Valery V. Fokin, M. G. Finn

Research output: Contribution to journalArticle

455 Citations (Scopus)

Abstract

(Chemical Equation Presented) A powerful engine: The Cu-catalyzed azide-alkyne cycloaddition depends on rapid formation of CuI- acetylide complexes from terminal alkynes 2 and their ability to activate organic azides 1. A kinetics study uncovered a bimolecular dependence on the metal and an unusually fast intramolecular variant of the process. The results suggest the importance of 3 as a reactive intermediate.

Original languageEnglish
Pages (from-to)2210-2215
Number of pages6
JournalAngewandte Chemie - International Edition
Volume44
Issue number15
DOIs
Publication statusPublished - 8 Apr 2005
Externally publishedYes

Fingerprint

Alkynes
Azides
Cycloaddition
Ligands
Engines
Kinetics
Metals

Keywords

  • Alkynes
  • Azides
  • Click chemistry
  • Copper
  • Cycloaddition

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Mechanism of the ligand-free CuI-catalyzed azide-alkyne cycloaddition reaction. / Rodionov, Valentin O.; Fokin, Valery V.; Finn, M. G.

In: Angewandte Chemie - International Edition, Vol. 44, No. 15, 08.04.2005, p. 2210-2215.

Research output: Contribution to journalArticle

Rodionov, Valentin O. ; Fokin, Valery V. ; Finn, M. G. / Mechanism of the ligand-free CuI-catalyzed azide-alkyne cycloaddition reaction. In: Angewandte Chemie - International Edition. 2005 ; Vol. 44, No. 15. pp. 2210-2215.
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