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Issue 17, 2011
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Copper(i)-catalyzed cycloaddition of silver acetylides and azides: Incorporation of volatile acetylenes into the triazole core

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Abstract

Silver acetylides and organic azides react under copper(I) catalysis to afford 1,4-disubstituted 1,2,3-triazoles. Mechanistic studies implicate a process involving transmetallation to copper acetylides prior to cycloaddition. This work demonstrates that silver acetylides serve as suitable precursors for entry into copper-mediated coupling reactions. This methodology allows the incorporation of volatile and difficult-to-handle acetylenes into the triazole core.

Graphical abstract: Copper(i)-catalyzed cycloaddition of silver acetylides and azides: Incorporation of volatile acetylenes into the triazole core

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Supplementary files

Article information


Submitted
08 Mar 2011
Accepted
03 Jun 2011
First published
03 Jun 2011

Org. Biomol. Chem., 2011,9, 6082-6088
Article type
Paper

Copper(I)-catalyzed cycloaddition of silver acetylides and azides: Incorporation of volatile acetylenes into the triazole core

I. Proietti Silvestri, F. Andemarian, G. N. Khairallah, S. Wan Yap, T. Quach, S. Tsegay, C. M. Williams, R. A. J. O'Hair, P. S. Donnelly and S. J. Williams, Org. Biomol. Chem., 2011, 9, 6082
DOI: 10.1039/C1OB05360D

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