Issue 13, 2023

Electrosynthesis of bridged or fused sulfonamides through complex radical cascade reactions: divergence in medium-sized ring formation

Abstract

Radical cascade addition is one of the most important and efficient strategies for the synthesis of valuable heterocycles with structural diversity and complexity. Organic electrochemistry has emerged as an effective tool for the sustainable molecular synthesis. Herein, we describe an electrooxidative radical cascade cyclization of 1,6-enynes to access two new classes of sulfonamides, containing medium-sized rings. Differences in the activation barrier for radical addition between alkynyl and alkenyl moieties contribute to the chemo-selective addition and regioselective 7- and 9-membered ring-formation. Our finding features good substrate scope, mild conditions, and high efficiency under metal-free and chemical oxidant-free conditions. In addition, the electrochemical cascade reaction allows for the concise synthesis of sulfonamides with bridged or fused ring systems containing medium-sized heterocycles.

Graphical abstract: Electrosynthesis of bridged or fused sulfonamides through complex radical cascade reactions: divergence in medium-sized ring formation

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Dec 2022
Accepted
20 Feb 2023
First published
21 Feb 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 3541-3547

Electrosynthesis of bridged or fused sulfonamides through complex radical cascade reactions: divergence in medium-sized ring formation

Y. Zhang, Z. Cai, C. Zhao, H. Zheng and L. Ackermann, Chem. Sci., 2023, 14, 3541 DOI: 10.1039/D2SC07045F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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