CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective
Abstract
Abstract CuI‐catalyzed alkyne–azide cycloaddition provides 1,4‐disubstituted 1,2,3‐triazoles with such efficiency and scope that the transformation has been described as “click” chemistry. An overview of the mechanism of this remarkable reaction is presented as a means to explain the myriad of experimental results, particularly the various methods of catalyst generation, solvent and substrate effects, and choice of base or ligand. Both solution‐phase and solid‐phase results are comprehensively examined. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
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In CuAAC, a [3+2] cycloaddition between an organic azide and a terminal alkyne gives a Cu(I)-catalyzed 1,4-disubstituted 1,2,3-triazole.
“In a CuAAC reaction, [3 + 2] cycloaddition occurs between an organic azide and a terminal alkyne to produce Cu(I)-catalyzed 1,4-disubstituted 1,2,3-triazole [187].”
From Quaternary ammonium-based biomedical materials: State-of-the-art, toxicological aspects and antimicrobial resistance (2017) · cites this paper as [187]
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- Authors
- Bock, V. D., Hiemstra, H., & van Maarseveen, J. H.
- Affiliations
- University of Amsterdam (NL)
- ORCID
- Hiemstra, Henk
- Venue
- European Journal of Organic Chemistry
- Publisher
- Wiley
- Published
- 2005-12-14
- Volume
- 2006
- Issue
- 1
- Pages
- 51-68
- ISSN
- 1099-0690 (ISSN-L)
- 1434-193X
- OpenAlex
- W2148075008
- Cited by
- 1,452
- References
- 107
- Citations by year
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- FWCI
- 56.05
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- European Journal of Organic Chemistry (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
- Physical Sciences › Chemistry › Organic Chemistry › Catalytic Alkyne Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Cycloaddition Reactions
- Keywords
- copper(I) iodide catalysis, azide-alkyne cycloaddition, click chemistry, 1,2,3-triazoles, reaction mechanism, solvent effects, base effects, ligand effects, solid-phase synthesis, wet chemical synthesis
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