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Copper‐Catalyzed Enantioselective Sonogashira Type Coupling of Alkynes with α‐Bromoamides

Xueling Mo, Bin Chen, Guozhu Zhang

2020Angewandte Chemie International Edition70 citationsDOI

Abstract

An asymmetric copper-catalyzed Sonogashira type coupling between alkynes and α-bromoamides has been developed. This method represents a facile approach to synthetically useful β, γ-alkynyl amides from two readily available starting materials in a highly enantioselective manner. A Bisoxazoline diphenylanaline (BOPA) serves as the effective chiral ligand. Preliminary mechanistic studies support the formation of alkyl radical species .

Topics & Concepts

Sonogashira couplingEnantioselective synthesisCopperCatalysisCombinatorial chemistryType (biology)ChemistryOrganic chemistryPalladiumBiologyEcologyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCatalytic Alkyne Reactions
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