Silver-Catalyzed Radical Aminofluorination of Unactivated Alkenes in Aqueous Media

Abstract

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