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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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Publication details

The article was received on 08 Mar 2011, accepted on 03 Jun 2011 and first published on 03 Jun 2011


Article type: Paper
DOI: 10.1039/C1OB05360D
Citation: Org. Biomol. Chem., 2011,9, 6082-6088
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    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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