A strategically novel protocol for ring-opening functionalization of aryl -difluorocyclopropanes (FCPs), which allows an expedient construction of CF-containing architectures via visible-light-promoted F-nucleophilic attack manifold, was disclosed. Single electron oxidation of FCPs was ascribed as the critical step for the success of this transformation by prompting F-nucleophilic attack, as well as the ensuing C-C bond scission. The observed intriguing regioselectivity for fluoroincorporation in this reaction was rationalized by invoking the cation-stabilization property of -difluorine substituents and also the thermodynamic gains acquired from forming CF functionality. By using cost-effective fluorination reagent and readily available substrates, a broad collection of structurally diversified α-allyl-β-trifluoromethyl ethylbenzene derivatives could be obtained in generally good yields. Further mechanistic investigations proved the engagement of a benzylic radical intermediate in this transformation.