Jump to main content
Jump to site search
SCHEDULED MAINTENANCE Close the message box

Maintenance work is planned for Monday 16 August 2021 from 07:00 to 23:59 (BST).

Website performance may be temporarily affected and you may not be able to access some PDFs or images. If this does happen, refreshing your web browser should resolve the issue. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 48, 2016

Metal-free radical thiolations mediated by very weak bases

Author affiliations

Abstract

Aromatic thioethers and analogous heavier chalcogenides were prepared by reaction of arene-diazonium salts with disulfides in the presence of the cheap and weak base NaOAc. The mild and practical reaction conditions (equimolar reagents, DMSO, r.t., 8 h) tolerate various functional groups (e.g. Br, Cl, NO2, CO2R, OH, SCF3, furans). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals.

Graphical abstract: Metal-free radical thiolations mediated by very weak bases

Supplementary files

Article information


Submitted
28 Oct 2016
Accepted
16 Nov 2016
First published
24 Nov 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 11347-11352
Article type
Communication

Metal-free radical thiolations mediated by very weak bases

D. Koziakov, M. Majek and A. Jacobi von Wangelin, Org. Biomol. Chem., 2016, 14, 11347 DOI: 10.1039/C6OB02276F

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.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements