Photoredox Catalyzed C-H Trifluoroethylamination Of Heteroarenes

Amines play an important role in chemistry and biology.The incorporation of fluorine-containing groups into amines could significantly change their conformation,basicity,lipophilicity,metabolic stability,and bioavailability.Among fluorine-containing amines,trifluoroethylamine is widely applied in the fields of medicine,pesticides and materials.Thus,the effective introduction of trifluoroethylamine group into organic compounds is great significant.Visible light is a clean and sustainable energy source.In this thesis,a visible light catalyzed trifluoroethylamination of heteroarenes from readily available N-trifluoroethyl-N-（tert-butoxycarbonyl）-4-trifluoromethylbenzene under mild conditions was developed.The advantages of the reaction includes simple operation,good to high yields,excellent regionselectivity,broad substrate scope,mild reaction conditions and direct C–H trifluoroethylamination.Various heteroarenes such as indole,benzofuran and benzothiophene and other heteroaromatic compounds were suitable substrates to give the corresponding trifluoroethylaminated products in moderate to good yields with excellent regioselectivities under the optimized conditions.The structures of all compounds were characterized by ~1H NMR,¹⁹F NMR,¹³C NMR and HRMS analysis.This method provides a new way to synthesize trifluoroethylamine compounds.