Synthesis of Homoallylic Amines by Radical Allylation of Imines with Butadiene under Photoredox Catalysis

Abstract

Ionic (2 e^- ) nucleophilic addition of allylmetal regents to imines dominates the synthesis of homo-allyl amine; however, single electron (1 e^- ) mediated imine allylation with feedstocks butadiene as an alternative allyl source remains unexplored. In this work, we report a conceptually different radical-radical cross-coupling strategy for the synthesis of a homoallyl amine between an α-amino alkyl radical and a transient allylic radical. This metal-free method provided a novel approach for the synthesis of homoallylic amines (>80 examples) from readily available materials with excellent regioselectivity and exceptional broad functional group compatibility.

Keywords: Allylic Compounds; Dienes; Photoredox Catalysis; Radical Reactions; Umpolung.