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Issue 48, 2016

Metal-free radical thiolations mediated by very weak bases

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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

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Article information

28 Oct 2016
16 Nov 2016
First published
24 Nov 2016

This article is Open Access

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

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

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