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

Silvestri, Ilaria Proietti, Andemarian, Fikre, Khairallah, George N., Yap, Su Wan, Quach, Tim, Tsegay, Sammi, Williams, Craig M., O'Hair, Richard A. J., Donnelly, Paul S. and Williams, Spencer 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. doi:10.1039/c1ob05360d


Author Silvestri, Ilaria Proietti
Andemarian, Fikre
Khairallah, George N.
Yap, Su Wan
Quach, Tim
Tsegay, Sammi
Williams, Craig M.
O'Hair, Richard A. J.
Donnelly, Paul S.
Williams, Spencer J.
Title Copper(I)-catalyzed cycloaddition of silver acetylides and azides: Incorporation of volatile acetylenes into the triazole core
Journal name Organic and Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2011
Sub-type Article (original research)
DOI 10.1039/c1ob05360d
Open Access Status Not Open Access
Volume 9
Issue 17
Start page 6082
End page 6088
Total pages 7
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2012
Language eng
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.
Keyword Alkyne Cycloaddition
Organic Azides
Click Chemistry
1,3-Dipolar Cycloaddition
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
School of Chemistry and Molecular Biosciences
 
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