Carboxylative Coupling of Chloromethyl(hetero)arenes with Allyltrimethoxysilane Catalyzed by Palladium Nanoparticles

Abstract

The palladium-catalyzed three-component coupling of either (chloromethyl)arenes or (chloromethyl)heteroarenes with allyltrimethoxysilane and carbon dioxide (i.e., a carboxylative Hiyama coupling reaction) successfully produced α,β-unsaturated esters in satisfactory to good yields. This reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles (NPs). A reaction mechanism, which includes the formation of an π-allylpalladium chloride intermediate, has been proposed.