Issue 19, 2024

Electrochemical 1,5-chlorosulfonylation and 1,5-hydrosulfonylation of vinylcyclopropanes

Abstract

An electrochemical 1,5-chlorosulfonylation and 1,5-hydrosulfonylation of vinylcyclopropanes is presented. This protocol offers a broad substrate scope, high functional group tolerance, and excellent E/Z selectivity under mild conditions, without the need for oxidants, reductants, or transition metals. Additionally, the process is easily scalable to the gram scale. The resulting products are valuable intermediates for the synthesis of quinolinone derivatives. Mechanism studies have indicated the involvement of a short radical chain propagation.

Graphical abstract: Electrochemical 1,5-chlorosulfonylation and 1,5-hydrosulfonylation of vinylcyclopropanes

Supplementary files

Article information

Article type
Research Article
Submitted
04 Jul 2024
Accepted
17 Aug 2024
First published
20 Aug 2024

Org. Chem. Front., 2024,11, 5564-5572

Electrochemical 1,5-chlorosulfonylation and 1,5-hydrosulfonylation of vinylcyclopropanes

X. Zhang, W. Li, Y. Zhou, S. Lv, L. Xu, L. Shi, Y. Li and D. Liang, Org. Chem. Front., 2024, 11, 5564 DOI: 10.1039/D4QO01228C

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