Issue 2, 2025

TMEDA-enabled regioselective sulfenylation of unprotected N-heterocycles via electrochemical sulfinyl radical generation

Abstract

An electrochemical sulfenylation of unprotected N-heterocycles with a wide range of commercially available arylsulfonyl chlorides was developed. This protocol features the use of inexpensive N,N,N′,N’-tetramethylethylenediamine (TMEDA) serving as both a promoter and a base to tune the sulfenylation process, thus affording sulfenylated products in good yields with high regioselectivity. Importantly, TMEDA significantly lowers the oxidation potential of indole, thus avoiding the over-oxidation of indole.

Graphical abstract: TMEDA-enabled regioselective sulfenylation of unprotected N-heterocycles via electrochemical sulfinyl radical generation

Supplementary files

Article information

Article type
Research Article
Submitted
22 Sep 2024
Accepted
16 Nov 2024
First published
27 Nov 2024

Org. Chem. Front., 2025,12, 684-689

TMEDA-enabled regioselective sulfenylation of unprotected N-heterocycles via electrochemical sulfinyl radical generation

Q. Zhong, X. Jiang, H. Gao, P. Wang and H. Li, Org. Chem. Front., 2025, 12, 684 DOI: 10.1039/D4QO01772B

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