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

Ilaria Proietti Silvestri, Fikre Andemarian, George N. Khairallah, Su Wan Yap, Tim Quach, Sammi Tsegay, Craig M Williams, Richard Alfred John O'Hair, Paul Stephen Donnelly, Spencer John Williams

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39 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)6082-6088
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number17
DOIs
Publication statusPublished - 7 Sep 2011
Externally publishedYes

Cite this

Proietti Silvestri, I., Andemarian, F., Khairallah, G. N., Wan Yap, S., Quach, T., Tsegay, S., Williams, C. M., O'Hair, R. A. J., Donnelly, P. S., & Williams, S. J. (2011). Copper(i)-catalyzed cycloaddition of silver acetylides and azides: Incorporation of volatile acetylenes into the triazole core. Organic and Biomolecular Chemistry, 9(17), 6082-6088. https://doi.org/10.1039/c1ob05360d