Synthesis of α-Keto Thioamides by Metal-Free C═C Bond Cleavage in Enaminones Using Elemental Sulfur.

An unprecedented method for cleaving the C═C bond in N, N-disubstituted enaminones in the presence of elemental sulfur and N, N-dimethyl-4-aminopyridine is disclosed. Without using any metal catalyst or additive, the cascade functionalization of both C═C and C-H bonds takes place to enable the formation of new C═S and C-N bonds, thus providing a facile and practical method for the synthesis of N, N-disubstituted α-keto thioamides.