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Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

Jiahao Ma, Shengtao Ding

2020Asian Journal of Organic Chemistry48 citationsDOI

Abstract

Abstract Metal‐catalyzed azide‐alkyne cycloaddition reactions represent the most convenient and atom‐economic way to construct robust 1,2,3‐triazole units. Remarkable copper‐ and ruthenium‐based catalytic systems have been well established for regioselective preparation of 1,4‐ and 1,5‐disubstituted 1,2,3‐triazoles, both of which have been widely utilized in various areas. In comparison, exploitation of efficient methods to promote the cycloaddition of azides with internal alkynes to afford 1,4,5‐trisubstituted 1,2,3‐triazole motifs with high regioselectivity is still challenging and attractive. This review provides a thorough summary of the developments in metal‐catalyzed cycloaddition of azides with internal alkynes. Besides discussions about mechanism and scope, applications of these strategies were also briefly overviewed.

Topics & Concepts

CycloadditionRegioselectivityChemistryCatalysisCombinatorial chemistryAlkyneAzideTriazoleTransition metalClick chemistryRutheniumOrganic chemistryClick Chemistry and ApplicationsChemical Synthesis and AnalysisCyclopropane Reaction Mechanisms
Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes | Litcius