In recent decades, hypervalent iodine reagents have emerged as a class of environmentally benign and tunable reactivity synthons, demonstrating remarkable advantages in radical fluoroalkylative difunctionalization of alkenes. This review systematically summarizes the recent advances in alkene difunctionalization involving cyclic hypervalent iodine reagents (Togni-I, Togni-II) and acyclic hypervalent iodine reagents. Through pathways such as radical addition, cross-coupling, migratory cyclization, and others, these reactions integrate fluoroalkylation, including trifluoromethylation, difluoromethylation, etc., with other functionalization processes such as (hetero)arylation, cyanation, amination, and azidation, achieving one-step difunctionalization of alkenes. This strategy has successfully constructed a series of fluorine-containing heterocycles and complex fluorinated molecular frameworks with chiral centers. Organized around cyclic and acyclic hypervalent iodine reagents, this article focuses on the strategies and mechanisms of various catalytic systems in controlling reaction selectivity and generality, aiming to provide insights for future applications of hypervalent iodine fluoroalkylation reagents in organic synthesis.