Silver-Catalyzed Radical Aminofluorination of Unactivated Alkenes in Aqueous Media

We report herein a mild and catalytic intramolecular aminofluorination of unactivated alkenes. Thus, with the catalysis of AgNO3, the reactions of various N-arylpent-4-enamides with Selectfluor reagent in CH2Cl2/H2O led to the efficient synthesis of 5-fluoromethyl-substituted gamma-lactams. A mechanism involving silver-catalyzed oxidative generation of amidyl radicals and silver-assisted fluorine atom transfer was proposed.