It is well-precedented that aryl radicals are capable of abstracting iodine atoms from alkyl iodides to form alkyl radicals and aryl iodides with a rate constant of k = 10 9 M -1 s -1 (Figure ). The iodine abstraction step is expected to be irreversible (rate constant of the reverse reaction k < 10 2 M -1 s -1 ) 42 due to the difference in the bond dissociation energy (BDE) of the C(sp 2 )-I bonds (BDE of iodobenzene = 65 kcal/mol) and C(sp 3 )-I bonds (BDE of isopropyl iodide = 56 kcal/mol). The high reactivity and irreversibility of the iodine abstraction step should outcompete other unwanted pathways of the aryl radicals, including the direct capture of aryl radicals by copper catalysts (k ≈ 10 8 M -1 s -1 ). Nonetheless, such a reactivity has received little attention in synthetic applications. We hypothesize that various alkyl iodides could be converted to alkyl radicals for copper catalysis via the use of the transient aryl radicals that could be readily generated via copper-catalyzed pathways, e.g., from arenediazonium salts. The SET to arenediazonium salts is a unique reactivity of Cu I complexes and has been widely involved in transformations of arenediazonium salts, including Sandmeyer reaction and Meerwein arylation. We postulate that such a productive merger of copper catalysis with aryl radical activation could provide a new strategy for the coupling of unactivated alkyl iodides with mild organometallic reagents (Figure ). As a proof of concept, in this work, we have exploited this new strategy to deliver a general approach to the difluoromethylation of alkyl iodides via a copper-catalyzed Negishi-type cross-coupling reaction (Figure ).