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Metal-free S-arylation of 5-mercaptotetrazoles and 2-mercaptopyridine with unsymmetrical diaryliodonium salts

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 20, Issue: 19, Page: 3890-3896
2022
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Article Description

Herein, we demonstrate the application of unsymmetrical iodonium salts towards S-arylation of heterocyclic thiols (especially tetrazole-5-thiols and pyridine-2-thiol) under metal-free conditions, affording a diverse range of di(hetero)aryl thioethers in moderate to good yields. A detailed study on the effects of counter-anions and the auxiliary of iodonium salts was conducted. Suitable auxiliary selection of the unsymmetrical iodonium salt offers flexibility for a wide range of aryl moieties and its incorporation into S-arylation. The DFT study supports the experimental observations of chemoselective arylation.

Bibliographic Details

Saikia, Raktim Abha; Hazarika, Nitumoni; Biswakarma, Nishant; Chandra Deka, Ramesh; Thakur, Ashim Jyoti

Royal Society of Chemistry (RSC)

Biochemistry, Genetics and Molecular Biology; Chemistry

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