The incorporation of difluoromethyl (CF2H) groups into organic molecules has recently received increasing attention largely owing to their unique hydrogen bonding ability. Due to the highly polarized C-H bond of the CF2H group-induced by the electron-withdrawing fluorine atoms-it can act as a lipophilic hydrogen bond donor. Recent studies showed that the hydrogen bonding ability of the CF2H group was comparable to that of hydroxyl, thiol, and amine groups. Therefore, the installation of CF2H groups has become a commonly used tactic in medicinal chemistry to modulate the lipophilicity and metabolic stability of lead drug candidates. One of the most straightforward approaches to the synthesis of CF2H-containing compounds is the direct difluoromethylation of the corresponding organohalides. Although transition metal catalysis has received great success in the difluoromethylation of aryl halides, the analogous reaction with unactivated alkyl halides remains a formidable challenge. Prakash has reported a nucleophilic substitution approach to the conversion of primary alkyl halides to their corresponding difluoromethyl phenyl sulfones, which were then transformed to the alkyl difluoromethanes using the sodium/mercury amalgam reduction. Very recently, the Shen group has reported an elegant Pd-catalyzed approach for the difluoromethylation of primary alkyl halides with TMSCF2H as the CF2H source along with stoichiometric copper iodide. Nonetheless, the limitation to primary alkyl halides and the use of large quantity of copper salts might dampen the synthetic utilities of these methods. Given the known iodine abstraction ability of aryl radicals, we questioned whether the aryl radical activation approach could be applied to enable a catalytic CF2Hinstallation protocol with significant utility to medicinal chemistry. We disclose herein the successful execution of this strategy and report a broadly applicable protocol for the catalytic conversion of alkyl iodides to alkyl difluoromethanes.