Here we describe a photoredox-catalyzed oxy-/aminofluoroalkylative cyclization of alkenes for coupling available Rf–I reagents to generate fluoroalkylated 2,3-dihydrobenzofuran and indolin derivatives with good to excellent yields under mild conditions. A wide range of functional groups are tolerated. The mechanistic investigation of radical trapping and cyclic voltammetry experiments proposed that a radical/SET (single electron transfer) pathway proceeded in this reaction.