Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 48, Pages 11347-11352Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob02276f
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- State of Bavaria
- Fonds der Chemischen Industrie (FCI)
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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.
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