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 language | English |
|---|---|
| Pages (from-to) | 1302-1315 |
| Number of pages | 14 |
| Journal | Chemical Society Reviews |
| Volume | 39 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2010 |
| Externally published | Yes |
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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 journal › Review article
}
TY - JOUR
T1 - Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond
T2 - New reactivity of copper(i) acetylides
AU - Hein, Jason E.
AU - Fokin, Valery V.
PY - 2010
Y1 - 2010
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=77949796395&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77949796395&partnerID=8YFLogxK
U2 - 10.1039/b904091a
DO - 10.1039/b904091a
M3 - Review article
C2 - 20309487
AN - SCOPUS:77949796395
VL - 39
SP - 1302
EP - 1315
JO - Chemical Society Reviews
JF - Chemical Society Reviews
SN - 0306-0012
IS - 4
ER -