Hypervalent fluoro-λ3-iodanes have emerged as versatile reagents that provide unusual fluorination selectivities under mild reaction conditions. Here, we report on adding a semipinacol rearrangement, fluorination, and aryl migration cascade reaction of styrene derivatives. Thus, various cyclopentanones became accessible in up to 96% yield, all bearing tertiary C,F-carbon centers adjacent to the ketone group. Such fluorinated structural motifs are difficult to build with previously established methods. Preliminary experiments on enantioselective processes validated that asymmetric transformations are likewise feasible.