To conclude, the century-old Sandmeyer reactions have taught the synthetic community one of the simplest ways of generating of aryl radicals. However, the reactivity of aryl radicals that received attention in synthetic chemistry was limited to either nucleophilic substitutions or the addition to unsaturated bonds. We report herein an aryl radical activation strategy that harnesses the halogen abstraction ability of aryl radicals, thus allowing unactivated alkyl iodides to participate in copper-catalyzed Negishi-type cross-coupling reactions. This aryl radical-enabled difluoromethylation reaction demonstrated high functional group tolerance and empowered late-stage modification of complex bioactive molecules. Mechanistic studies indicated that the rapid iodine atom abstraction by aryl radicals contributed the success of this strategy. Given the rich medicinal potential of CF2H groups and the broad availability of alkyl halides, we anticipate that this protocol will find wide application in drug development. Most important, we expect that this aryl radical activation strategy will be a general paradigm to the development of a diverse range of C-C and C-heteroatom bond-forming reactions.