Journal
NEW JOURNAL OF CHEMISTRY
Volume 46, Issue 2, Pages 582-591Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1nj04892a
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Funding
- IIT Kanpur
- UGC, New Delhi
- Science and Engineering Research Board (SERB), India [SB/S2/JCB-52/2014]
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This study investigated the reaction pathways of aryl olefins and thiols in the presence of Oxone in different solvent systems, revealing two distinct reaction pathways leading to the synthesis of two different products.
The reaction between aryl olefins and thiols in the presence of Oxone in toluene-water (9 : 1, v/v) affords beta-hydroxy-2-arylethyl aryl sulfides smoothly by the interception of intermediary thiyl radicals with aryl olefins; the former are generated by the oxidation of thiols with Oxone in a biphasic medium. However, the change of the solvent system to acetonitrile-water facilitates a nonradical and concerted pathway leading to 2-arylethyl aryl sulfones exclusively via a tandem click reaction followed by oxidation. In essence, 'oxidative addition' is facilitated in a toluene-water medium, while 'addition-oxidation' is promoted in acetonitrile-water. Given that Oxone is readily available, environmentally benign, and cheap, solvent-mediated switching constitutes facile and direct access to two disparate products, namely, beta-hydroxy-2-arylethyl aryl sulfides and 2-arylethyl aryl sulfones.
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