Multicomponent Reactions in Open-Air Metal-Free Aqueous Visible-Light Catalysis: Radical–Polar Crossover toward γ-Lactams and γ-Aminobutyric Acids

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Authors: Gui-Ting Song, Liu Su-ya, Ying Cheng, Shi-You Xue, Shanshan Chen, Wenkai Zong, Lin Zhu, Nian Wang, Li-Min Zhang, Yuan Zhou, Xue-Ying Yang, Lan-Bin He
+2 more J N Li, Chuan‐Hua Qu
Cited by: 4
References: 35

Abstract

A green and sustainable synthetic protocol for γ-lactams is developed herein via metal-free three-component photocatalysis using pure water as the sole solvent. This strategy combines the advantages of visible-light activation, one-pot multicomponent coupling, and aqueous-phase synthesis, overcoming the drawbacks of traditional methods such as organic solvent pollution, transition metal residues, and harsh conditions. Employing inexpensive and readily available N -arylglycines, acrylates, and 1,1-diarylethylenes as starting materials, this method enables two consecutive C–C bond-forming events to access a variety of valuable yet otherwise difficult-to-access γ-lactams and γ-aminobutyric acid (GABA) derivatives. Mechanistically, photoredox activation of N -arylglycines generates α-amino radicals upon decarboxylation, which undergo sequential radical addition with acrylic phenol esters and 1,1-diarylethylenes, followed by cyclization to form the pyrrolidinone core. The synthetic utility is further demonstrated by the preparation of δ-amino alcohols and γ-aminobutyric acids together with preliminary asymmetric synthesis studies.

Fields of Study & Subjects

Radical Photochemical Reactions Catalytic Cross-Coupling Reactions Catalytic C–H Functionalization Methods

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
18
Pages
5728–5733
Publication date
24 April 2026
Language
EN