A new method for aromatic monofluoromethylation was developed. Aryl iodides can be efficiently transformed into the corresponding monofluoromethylated products by a copper-catalyzed debenzoylative fluoroalkylation with 2-PySO2CHFCOR and subsequent reductive desulfonylation. The (2-pyridyl)sulfonyl moiety plays an important role in the copper-catalyzed cross-coupling, and it can be removed easily through Bu3SnH-mediated desulfonylation.