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

The perfluoroalkylsulfonylation (CF 3 SO 2 , C 2 F 5 SO 2 and CHF 2 SO 2 ) in the enaminone C H 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 C H bond elaboration and C C double bond configuration inversion by free radical process. The C H 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 C H perfluoroalkylsulfonylation, this work features advantage of metal-free conditions, novel and selective stereoselectivity and broad substrate tolerance.