Dithiocarbamate mediated thioamidation via C–C single bond cleavage of styrene: study of the protocol in decarbonylative and decarboxylative thioamidations

Abstract

Dithiocarbamate salts have been explored in a novel C–C thioamidation of styrene in the presence of ammonium persulfate and molecular oxygen. A series of thioamide compounds with different structural variations have been prepared in good yields. Various cyclic/acyclic secondary amine, aromatic amine, benzylamine and amino acid based thioamides have been prepared following the protocol. The protocol has further been applied to decarbonylative thioamidation of benzaldehyde and toluene and decarboxylative thioamidation of benzoic acid. The reaction mechanism has been proposed by isolation of the reaction intermediate and GC-MS analysis of the reaction mixture. The post-synthetic potential of the synthesized thioamide has been checked through a C–C cross-coupling reaction via C–N bond cleavage.