We demonstrate a ligand- and glovebox-free regioselective direct C(3)-H imidation of 2-pyridones and also benzylic-type imidation of 2-pyridones bearing a methyl substituent employing Cu(OAc)2·H2O as the catalyst and N-fluorobenzenesulfonimide (NFSI) as an imidating reagent. A broad range of imidated 2-pyridone derivatives is made up to excellent yields. The present strategy operates well on a gram scale, and the ensuing product can be readily subjected to mono- and bis-desulfonylation reactions.