A Versatile, Electrophilic Reagent for Monofluoromethylthiolation

A new electrophilic monofluoromethylthiolating reagent N-fluoromethylthiophthalimide PhthSCH(2)F 1 was developed. Reagent 1 could be readily synthesized from easily available starting materials benzyl mercaptan and CH2FCl in three steps. N-Fluoromethylthiophthalimide 1 is a powerful electrophilic monofluoromethylthiolating reagent that allows the monofluoromethylthiolation of a wide range of nucleophiles including alkynes, aryl/vinyl boronic acids, electron-rich heteroarenes, beta-ketoesters and oxindoles, as well as thiols under mild conditions.