The　redox-neutral　palladium-catalyzed　dicarbofunctionalization　of　unactivated　alkenes　with　a　variety　of　functionalized　difluoromethyl　and　perfluoroalkyl　halide　is　presented　here.　This　transformation　proceeds　smoothly　at　low　temperatures　and　enables　the　assembly　of　diversified　fluoroalkylated　pyrrolo[1,2-a]indole　derivatives　with　one　all-carbon　quaternary　center　in　high　regioselectivity.　Mechanistic　studies　suggested　an　operative　radical　mechanism　and　the　initiation　of　the　inner-sphere　single　electron　transfer　between　a　dual　phosphine　ligand-coordinated　palladium(0)　species　and　perfluoroalkyl　halides.