The proposed mechanism for the aryl radical-enabled, copper-catalyzed difluoromethylation of alkyl iodides is outlined in Figure . We reason that the transmetallation of a Cu I catalyst 1 with a zinc-difluoromethyl reagent, (DMPU)2Zn(CF2H)2 2, i.e., Vicic-Mikami reagent, could form a Cu I -CF2H species 3. Notably, a hectogram synthesis of 2 has been recently reported by Pfizer. Our previous work has suggested that Cu I -CF2H species 3 was a strong reductant (cal'd Ered = -1.2 V vs SCE). Therefore, we anticipate that 3 could undergo a SET event with a diazonium salt 4 to form an aryl radical intermediate 5, with the concurrent formation of a Cu II -CF2H complex 6. The former should efficiently abstract an iodine atom from an alkyl iodide 7 to form an alkyl radical 8 and an aryl iodide 9. Oxidative capture of 8 by the Cu II -CF2H species 6 would furnish a highvalent organocopper(III) complex 10, which should undergo reductive elimination to afford the alkyl difluoromethane coupling product 11. This reductive elimination step would regenerate the starting Cu I catalysts and close the catalytic cycle.