Photoredox/Copper-Catalyzed One-Pot Aminoalkylation/Cyclization of Alkenes with Primary Amines to Synthesize Polysubstituted γ-Lactams

Org Lett. 2024 Feb 2;26(4):845-849. doi: 10.1021/acs.orglett.3c03974. Epub 2024 Jan 22.

Abstract

Visible-light-driven chemical transformation has emerged as a powerful tool for the synthesis of γ-lactams. However, during this transformation, the α-bromoimides need to be pre-prepared. Herein, we report a photoreodox/copper-catalyzed one-pot three-component reaction of alkenes with primary amines for the construction of γ-lactams. In this transformation, the orthoquinones were generated via a photocatalytic pathway, followed by attack by Cu-amido complexes and intramolecular cyclization to give the γ-lactams. This method represents a simple synthetic route displaying broad functional group tolerance, including substrates bearing alcohols, ketones, heterocycles, esters, halides, alkynes, nitriles, ethers, etc.