Issue 23, 2020

Sustainable access to sulfonic acids from halides and thiourea dioxide with air

Abstract

A sustainable and mild one-step strategy is explored for the synthesis of aryl and alkyl sulfonic acids using a facile combination of halides and sulfur dioxide surrogates under air. The cheap industrial material thiourea dioxide was employed as an eco-friendly and easy-handling sulfur dioxide surrogate, while air was used as a green oxidant. Both aryl and alkyl sulfonic acids were obtained under transition metal-catalyzed or transition metal-free conditions. Mechanistic studies demonstrated that sulfinate was involved as an intermediate in this transformation. Notably, this protocol has been applied to the late-stage sulfonation of the drugs naproxen, isoxepac and ibuprofen.

Graphical abstract: Sustainable access to sulfonic acids from halides and thiourea dioxide with air

Supplementary files

Article information

Article type
Communication
Submitted
16 Sep 2020
Accepted
23 Oct 2020
First published
23 Oct 2020

Green Chem., 2020,22, 8238-8242

Sustainable access to sulfonic acids from halides and thiourea dioxide with air

H. Zhang, M. Wang and X. Jiang, Green Chem., 2020, 22, 8238 DOI: 10.1039/D0GC03135F

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