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

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

doi:10.1002/anie.200461496

Mechanism of the ligand-free Cu^I-catalyzed azide-alkyne cycloaddition reaction

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

573 Scopus citations

Abstract

(Chemical Equation Presented) A powerful engine: The Cu-catalyzed azide-alkyne cycloaddition depends on rapid formation of Cu^I- 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 language	English (US)
Pages (from-to)	2210-2215
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	15
DOIs	https://doi.org/10.1002/anie.200461496
State	Published - Apr 8 2005
Externally published	Yes

Keywords

Alkynes
Azides
Click chemistry
Copper
Cycloaddition

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.200461496

Cite this

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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.",

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KW - Copper

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