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The perfluoroalkylsulfonylation (CF3SO2,C2F5SO2 and CHF2SO2) 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 o-perfluoroalkylsulfonyl enaminones has been realized via unprecedented C-H bond elaboration and C=C double bond configura-tion inversion by free radical process.