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

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)center dot 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.