Abstract
The reaction between arenediazonium tetrafluoroborates and sodium arenethlolates in Me 2SO at 25°C represents an efficient access to diaryl sulfides. A number of evidences suggest the occurrence of a radical, radical-anion S RNl mechanism, the arenethlolate acting both as electron donor and as aryl-radical trapping nucleophile. Valuable improvements with respect to recent S RNl syntheses of diaryl sulfides from haloarenes are represented. Inter alia , by the compatibility of both electron-withdrawing and releasing substituents as well as by the insensitivity to steric hindrance In the diazonlum salt. When the arenedlazonlum ion bears another S RNl leaving group (such as Cl, Br, or I) disubstitution products are predomnantly formed.
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