NBS-promoted regioselective thiocyanatothiolation of alkenes with free thiols and NH4SCN

Wei Chen; Run Wu; Wanxiang Wang; Haiping Zhou; Mingyue Fu

doi:10.1039/D4OB02020K

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

NBS-promoted regioselective thiocyanatothiolation of alkenes with free thiols and NH₄SCN†

Wei Chen,

*^a Run Wu,^a Wanxiang Wang,^a Haiping Zhou^a and Mingyue Fu^a

Author affiliations

* Corresponding authors

^a Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, China
E-mail: chenweicstq@163.com

Abstract

An efficient NBS-promoted three-component thiocyanatothiolation of alkenes with free thiols and NH₄SCN has been developed. This protocol avoids tedious preactivation of thiols and employs a diverse range of accessible thiols directly as sulfur sources. Moreover, the reaction exhibits regioselectivity and shows high compatibility with styrenes and unactivated alkenes. Preliminary mechanism studies revealed that both a radical pathway and thiol-oxidation-coupling were involved in this protocol.

Download options Please wait...

Supplementary files

Supplementary information PDF (8445K)

Transparent peer review

To support increased transparency, we offer authors the option to publish the peer review history alongside their article.

View this article’s peer review history

Article information

DOI: https://doi.org/10.1039/D4OB02020K
Article type: Paper
Submitted: 13 Dec 2024
Accepted: 27 Jan 2025
First published: 28 Jan 2025

Download Citation

Org. Biomol. Chem., 2025, Advance Article

Permissions

Request permissions

NBS-promoted regioselective thiocyanatothiolation of alkenes with free thiols and NH₄SCN

W. Chen, R. Wu, W. Wang, H. Zhou and M. Fu, Org. Biomol. Chem., 2025, Advance Article , DOI: 10.1039/D4OB02020K

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.

Organic & Biomolecular Chemistry