Metal-free C(sp2)-H perfluoroalkylsulfonylation and configuration inversion: Stereoselective synthesis of α-perfluoroalkylsulfonyl E-enaminones

The perfluoroalkylsulfonylation (CF3SO2, C2F5SO2 and CHF2SO2) in the enaminone CH bonds has been developed simply via the promotion of molecular iodine by using stable and cheap sodium perfluoroalkyl sulfinates as coupling partners. The stereoselective synthesis of E-configurated α-perfluoroalkylsulfonyl enaminones has been realized via unprecedented CH bond elaboration and CC double bond configuration inversion by free radical process. The CH perfluoroalkylsulfonylation of enaminones leading to the synthesis diverse perfluoroalkyl functionalized enamines is realized via the promotion of molecular iodine. As the first method in enaminone CH perfluoroalkylsulfonylation, this work features advantage of metal-free conditions, novel and selective stereoselectivity and broad substrate tolerance. [Display omitted]