Pd-Catalyzed Coupling of Thioamides with N-Tosylhydrazones/Trapping by Esters Cascade Reaction

N,N-Disubstituted thioamides coupled with N-tosylhydrazones under Pd(TFA)(2)/(t)BuXPhos catalyst and (NaOBu)-Bu-t, and the intermediates from palladium carbene migratory insertion containing beta-hydrogen were trapped by intramolecular esters activated by BF3 center dot Et2O instead of undergoing beta-H elimination, providing polyfunctional thiophen-3(2H)-ones with sulfur-containing tetrasubstituted carbon centers in moderate to good yields. The reaction features the formation of three bonds in a single operation, odorless, safe, and easily available substrates, wide substrate scope, and excellent functional group tolerance.

Automated summary

The reaction involves the coupling of N,N-disubstituted thioamides with N-tosylhydrazones under the catalysis of Pd(TFA)(2)/(t)BuXPhos and (NaOBu)-Bu-t, resulting in the formation of polyfunctional thiophen-3(2H)-ones with sulfur-containing tetrasubstituted carbon centers in moderate to good yields. The reaction showcases the efficient formation of three bonds in a single operation, with odorless, safe, and easily available substrates, a wide substrate scope, and excellent tolerance towards different functional groups.