Visible-light-induced defluorinative allylation of difluoromethyl ketones using alkylamines as bifunctional agents

Abstract

A visible-light-induced alkylamine-facilitated reductive defluoroallylation of difluoromethyl ketones with allylic chlorides is reported, enabling efficient access to α-fluoro alkenylketones with high efficiency under catalyst-free and mild conditions. In this reaction, alkyl amines function as bifunctional agents: an electron donor for forming an electron donor–acceptor complex to trigger the selective C–F bond cleavage of CF₂H-ketones and a halogen-atom transfer agent for activating the C–Cl bond of allylic chlorides. This protocol exhibits a broad substrate scope of CF₂H-ketones and allylic halides. Synthetic derivatizations of the resulting α-fluoro alkenylketones and preliminary mechanistic studies have been presented.