Electrochemical [3 + 2] cycloaddition of anilines and enamine ketones: construction of 3-benzoylindole derivatives

Abstract

This article describes an eco-friendly and atom-economical electrochemical protocol for the intermolecular [3 + 2] cycloaddition to synthesize 3-benzoylindole derivatives in synthetically viable yields. The oxidative cycloaddition proceeds under transition-metal-free and strong-oxidant-free conditions, generating H2 and (Me)2NH as the byproducts, thereby aligning with green chemistry principles. Furthermore, the methodology exhibits exceptional synthetic versatility through successful late-stage diversification and compatibility with structurally diverse substrates. Preliminary cytotoxic evaluation via CCK-8 assays against two human carcinoma cell lines revealed potent bioactivity profiles, establishing a foundation for systematic exploration of indole-based pharmacophores. This protocol offers a sustainable alternative to conventional synthetic strategies while expanding the functionalization landscape of heteroaromatic systems.

Graphical abstract: Electrochemical [3 + 2] cycloaddition of anilines and enamine ketones: construction of 3-benzoylindole derivatives

Supplementary files

Article information

Article type
Paper
Submitted
19 May 2025
Accepted
15 Jul 2025
First published
18 Jul 2025

Org. Biomol. Chem., 2025, Advance Article

Electrochemical [3 + 2] cycloaddition of anilines and enamine ketones: construction of 3-benzoylindole derivatives

Y. Hu, C. Yu, Y. Ran, M. Yu, J. Sun, H. Liu, J. Zhang, H. Wang and L. Liu, Org. Biomol. Chem., 2025, Advance Article , DOI: 10.1039/D5OB00831J

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