Dithiocarbamate-mediated thioamidation of arylglyoxylic acids by decarboxylative–decarbonylative C–C bond formation reactions

Abstract

Arylglyoxylic acids have been employed in a novel decarboxylative–decarbonylative thioamidation reaction with dithiocarbamate intermediates prepared in situ by the prompt reaction of amines and carbon disulfide. A series of thioamide compounds were synthesized using different arylglyoxylic acids, various secondary amines, a primary amine, aniline, and an amino acid derivative. The reaction is proposed to proceed via an acyl radical intermediate in the presence of a persulfate oxidant and a Pd(II)-catalyst.