Visible-Light Promoted Radical Fluoroalkylation of O- and N-Substituted Alkenes.

Abstract

Interaction of enol ethers enol acetates, enamides and enamines with fluorinated reagents may be considered as a reliable method for the synthesis of organofluorine compounds. While classic nucleophile/electrophile substitution or addition mechanisms cannot be realized for coupling of these components, their intrinsic reactivities are revealed with the aid of photoredox catalysis. A combination of these electron donating and accepting components provides a perfect balance needed for individual redox steps, which in some cases may proceed even without a photocatalyst. The same electronic factors also support the key C,C-bond forming event involving addition of fluorinated radical at the electron rich double bond.