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A Chemoselective and Desulfurative Chan–Lam Coupling: C–N Bond Formation between Benzimidazoline‐2‐Thiones and Arylboronic Acids
Author(s) -
Chen JinQuan,
Liu Xing,
Guo Jia,
Dong ZhiBing
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000075
Subject(s) - chemistry , catalysis , chemoselectivity , substrate (aquarium) , combinatorial chemistry , ligand (biochemistry) , solvent , organic chemistry , medicinal chemistry , biochemistry , oceanography , receptor , geology
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 · H 2 O, 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.