Practical copper-catalyzed chloronitration of alkenes with TMSCl and guanidine nitrate

Abstract

A novel and practical chloronitration of alkenes in the presence of easily available TMSCl and guanidine nitrate has been developed by using cheap copper sulfate pentahydrate as the catalyst. A variety of vic-chloronitro compounds were directly synthesized in good to excellent yields on up to 100 mmol scale under mild reaction conditions, and the resulting products could be smoothly transformed into the corresponding nitroalkenes and diverse nitro compounds bearing a vicinal nucleophilic “C”, “N” or “S” unit.