A Chemoselective and Desulfurative Chan–Lam Coupling: C–N Bond Formation between Benzimidazoline-2-Thiones and Arylboronic Acids

Article abstract of DOI:10.1002/ejoc.202000075

An efficient method for the chemoselective and desulfurative Chan–Lam cross-coupling based on benzimidazoline-2-thiones was developed. By modulating the amount of the catalyst Cu(OAc)₂·H₂O, alkali, temperature, and solvent, the desulfurizational C–N bond formation product (N-arylbenzimidazoles) could be selectively furnished smoothly. The features of this protocol are an inexpensive and readily available catalyst, ligand-free conditions, wide substrate scope, easy performance, and moderate to excellent yields. It shows potential synthetic value for the preparation of a diversity of arylbenzoheterocyclic compounds, which are potentially active in pharmaceuticals and agrochemicals.