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Copper-Catalyzed One-Step Formation of Four C–N Bonds toward Polyfunctionalized Triazoles via Multicomponent Reaction

Xuelun Duan, Nan Zheng, Gongbo Liu, Ming Li, Qiming Wu, Xinhao Sun, Wangze Song

2022Organic Letters22 citationsDOI

Abstract

-azirines has been developed for the first time by the efficient formation of four C-N bonds in one step under mild conditions, rapidly preparing polyfunctionalized triazoles with molecular diversity involving three different intermediates of copper-acetylide, copper-allenylidene, and copper-vinyl nitrene. Propargylic ester is disclosed as a "three-in-one" building block possessing triplicate cycloaddition and nucleophilic and electrophilic properties, which could enable such a four-component transformation by high yields, broad substrate scope, and functionalization.

Topics & Concepts

ChemistryCatalysisCopperCombinatorial chemistryOrganic chemistryPolymer chemistryClick Chemistry and ApplicationsChemical Synthesis and AnalysisCatalytic C–H Functionalization Methods
Copper-Catalyzed One-Step Formation of Four C–N Bonds toward Polyfunctionalized Triazoles via Multicomponent Reaction | Litcius