Direct trifluoromethylselenolations of electron-rich (hetero)aromatic rings with N-trifluoromethylselenolating saccharin

Abstract

A novel, easily synthesizable, shelf-stable electrophilic trifluoromethylselenolating reagent, N-trifluoromethylselenosaccharin, has been developed. This reagent can be synthesized in good yield by a two-step one-pot reaction from BnSeCF₃, SO₂Cl₂, and silver saccharin. N-Trifluoromethylselenosaccharin proves to be an efficient trifluoromethylselenolating reagent, enabling the direct trifluoromethylselenolation of various electron-rich aromatic and heteroaromatic rings under mild reaction conditions. It exhibits excellent chemoselectivity and excellent compatibility with various functional groups, making it suitable for late-stage trifluoromethylselenolation applications in complex natural product and drug synthesis.