Metal-free radical thiolations mediated by very weak bases?
Organic & Biomolecular Chemistry Pub Date: 2016-11-24 DOI: 10.1039/C6OB02276F
Abstract
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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