Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond

New reactivity of copper(i) acetylides

Jason E. Hein, Valery V. Fokin

Research output: Contribution to journalReview article

1209 Citations (Scopus)

Abstract

Copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a widely utilized, reliable, and straightforward way for making covalent connections between building blocks containing various functional groups. It has been used in organic synthesis, medicinal chemistry, surface and polymer chemistry, and bioconjugation applications. Despite the apparent simplicity of the reaction, its mechanism involves multiple reversible steps involving coordination complexes of copper(i) acetylides of varying nuclearity. Understanding and controlling these equilibria is of paramount importance for channeling the reaction into the productive catalytic cycle. This tutorial review examines the history of the development of the CuAAC reaction, its key mechanistic aspects, and highlights the features that make it useful to practitioners in different fields of chemical science.

Original languageEnglish
Pages (from-to)1302-1315
Number of pages14
JournalChemical Society Reviews
Volume39
Issue number4
DOIs
Publication statusPublished - 2010
Externally publishedYes

Fingerprint

Alkynes
Azides
Cycloaddition
Copper
Coordination Complexes
Functional groups
Polymers
Pharmaceutical Chemistry

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond : New reactivity of copper(i) acetylides. / Hein, Jason E.; Fokin, Valery V.

In: Chemical Society Reviews, Vol. 39, No. 4, 2010, p. 1302-1315.

Research output: Contribution to journalReview article

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