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Synthesis of β-Polychlorinated Alkynes Enabled by Copper-Catalyzed Multicomponent Reaction

Qiuzhu Wang, Mengning Wang, Qianhui Wu, Mengtao Ma, Binlin Zhao

2022Organic Letters19 citationsDOI

Abstract

Functional molecules bearing polychlorinated moieties usually play versatile roles in organic synthesis and biochemistry. A copper-catalyzed multicomponent polychloro-carboalkynylation of alkenes presents an efficient and operationally simple approach for the synthesis of β-polychlorinated alkynes. Mechanistic experiments were conducted demonstrating that an in situ generated copper acetylide complex was the real catalyst and reactive intermediate during the copper-catalytic cycle. And enantioselective exploration demonstrated potential application for the synthesis of chiral β-polychlorinated alkynes.

Topics & Concepts

ChemistryCopperCatalysisAcetylideEnantioselective synthesisCombinatorial chemistryOrganic chemistryMoleculeIn situPhotochemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsAsymmetric Hydrogenation and Catalysis