Photocatalytic Synthesis of Homoallylic Amines via Nucleophilic Addition of Nickel Allyl Complexes to Imines

Abstract

Homoallylic amines can be found in pharmaceutically interesting molecules and are versatile building blocks for total synthesis. Herein, we present a three-component coupling reaction of an aldehyde, an aniline and an allylic carbonate or allene to yield branched homoallylic amines in good yields and diastereoselectivity. Our straightforward protocol proceeds via the addition of an allyl nickel species to an in situ formed imine and represents the first photocatalytic realization of the classic approach of allyl metal addition to imines. Next to some follow-up transformations, a detailed reaction mechanism backed by experimental observations is presented.