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Palladium-Catalyzed Four-Component Carbonylative Cyclization Reaction of Trifluoroacetimidoyl Chlorides, Propargyl Amines, and Diaryliodonium Salts: Access to Trifluoromethyl-Containing Trisubstituted Imidazoles

Zhengkai Chen, Weifeng Wang, Hefei Yang, Xiao‐Feng Wu

2020Organic Letters50 citationsDOI

Abstract

A palladium-catalyzed four-component carbonylative cyclization reaction for the expeditious construction of trifluoromethyl-containing trisubstituted imidazoles has been achieved. With readily accessible trifluoroacetimidoyl chlorides, propargyl amines, and diaryliodonium salts as the starting materials, the carbonylative transformation proceeds smoothly under mild conditions to enable the formation of multifunctionalized imidazole molecules in a one-pot, one-step manner. Diaryliodonium salts serve as both oxidants and aryl sources in the reaction.

Topics & Concepts

ChemistryPropargylTrifluoromethylArylCatalysisPalladiumImidazoleCombinatorial chemistryOrganic chemistryMoleculeAlkylCatalytic C–H Functionalization MethodsFluorine in Organic ChemistryCatalytic Cross-Coupling Reactions