Photoredox‐Catalyzed Synthesis of Homoallylamines from Unactivated Imines and Allyl Bromides

Abstract

Abstract A photoredox‐catalyzed umpolung strategy for the synthesis of homoallylamines from unactivated imines and allyl bromides is described. This strategy exploited N , N ‐diisopropylethylamine (DIPEA) as an auxiliary agent to indirectly realize the cross‐coupling of imines and allyl bromides. Various sterically hindered homoallylamines were synthesized by combining photocatalysis with halogen atom transfer (XAT). Notable characteristics of this approach include water‐insensitive reaction conditions, high yield (up to 99%), wide substrate scope (suitable for N ‐aryl/alkyl and C‐ aryl ketimines and aldimines, 39 examples), and high tolerance of functional groups (such as cyano, ester, amide, and thioamide).