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- Title
An Expedient Iodine‐Catalyzed Synthesis of Unsymmetrical Thiosulfonates by Sulfonylation of Thiols using Sulfonyl hydrazides in the Presence of Oxone.
- Authors
Yadav, Navin; Payra, Soumen; Narasimha Moorthy, Jarugu
- Abstract
A metal‐free and green iodine‐catalyzed protocol is described herein for the synthesis of unsymmetrical thiosulfonates by sulfonylation of thiols using I2/Oxone. It's shown that oxidative cross‐coupling of thiyl radicals with sulfonyl radicals – generated from thiols and sulfonyl hydrazides, respectively, by the redox chemistry between thiol/Oxone and I2/Oxone – occurs in a facile manner at rt, providing access to unsymmetrical thiosulfonates. Diverse unsymmetrical thiosulfonates are synthesized in good‐to‐excellent isolated yields by the reactions of aryl/(hetero)aryl/alkyl thiols with a variety of aryl/(hetero)aryl/alkyl/benzyl sulfonyl hydrazides. The protocol can be further extended to the synthesis of alkyl/aryl sulfonate esters by the reactions of sulfonyl hydrazides with alcohols/phenols using I2/Oxone.
- Subjects
HYDRAZIDES; PEROXYMONOSULFATE; ARYL esters; CHEMICAL yield; SULFONYL compounds; SULFONYL chlorides; SULFONATES; THIOLS
- Publication
Asian Journal of Organic Chemistry, 2022, Vol 11, Issue 12, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202200554