Electrochemical [3+2] Cycloaddition of Anilines and Enamine ketone: Construction of 3-benzoylindole derivatives

Abstract

This article describes an eco-friendly and atom-economical electrochemical protocol for the intermolecular [3+2] cyclization to synthesize 3-benzoylindole derivatives in synthetically viable yields. The oxidative annulation proceeds under transition-metal-free and strong-oxidant-free conditions, generating H₂ and (Me)2NH as the byproduct, 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.

Supplementary files

Article information

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

Org. Biomol. Chem., 2025, Accepted Manuscript

Electrochemical [3+2] Cycloaddition of Anilines and Enamine ketone: 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, Accepted Manuscript , DOI: 10.1039/D5OB00831J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements