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 A. J. O'Hair; Paul S. Donnelly; Spencer J. Williams

doi:10.1039/C1OB05360D

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

Ilaria Proietti Silvestri,^a Fikre Andemarian,^a George N. Khairallah,^a Su Wan Yap,^a Tim Quach,^a Sammi Tsegay,^a Craig M. Williams,^b Richard A. J. O'Hair,^a Paul S. Donnelly^a and Spencer J. Williams*^a

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^a School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Victoria, Australia
E-mail: sjwill@unimelb.edu.au
Fax: +61 3 9347 8124
Tel: +61 3 8344 2422

^b School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, Queensland, Australia

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.

Organic & Biomolecular Chemistry

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

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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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