Oxidative 12-carboamination of alkenes with alkyl nitriles and amines toward γ-amino alkyl nitriles

摘要

Difunctionalization of alkenes has become a powerful tool for quickly increasing molecular complexity in synthesis. Despite significant progress in the area of alkene difunctionalization involving the incorporation of a nitrogen atom across the C–C double bonds, approaches for the direct 1,2-carboamination of alkenes to produce linear N-containing molecules are scarce and remain a formidable challenge. Here we describe a radical-mediated oxidative intermolecular 1,2-alkylamination of alkenes with alkyl nitriles and amines involving C(sp³)–H oxidative functionalization catalysed by a combination of Ag2CO3 with iron Lewis acids. This three-component alkene 1,2-alkylamination method is initiated by the C(sp³)–H oxidative radical functionalization, which enables one-step formation of two new chemical bonds, a C–C bond and a C–N bond, to selectively produce γ-amino alkyl nitriles.