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Zinc Mediated Azide-Alkyne Ligation to 1,5- and 1,4,5-Substituted 1,2,3-Triazoles

Christopher D. Smith and Michael F. Greaney *

*School of Chemistry, University of Manchester, Manchester, M13 9PL, U.K., Email: michael.greaneymanchester.ac.uk

C. D. Smith, M. F. Greaney, Org. Lett., 2013, 15, 4826-4829.

DOI: 10.1021/ol402225d (free Supporting Information)


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Abstract

A mild, zinc-mediated method for regioselective formation of 1,5-substituted 1,2,3-triazoles from a wide range of azides and alkynes works at room temperature. Additionally, the triazole 4-position can be further functionalized by reaction of the intermediate aryl-zinc with various electrophiles to accommodate a diverse three-component coupling strategy.

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proposed mechanistic pathway



Key Words

Huisgen 1,3-dipolar cycloaddition, 1,2,3-Triazoles


ID: J54-Y2013