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Described herein is a process that accomplishes the iodine-promoted C-H sulfidation of electron-deficient fluorine-containing aromatic compounds with benzenethiols. This method effectively enables the unsymmetrical bis-sulfidation of pentafluorobenzene. Also, this oxidizing system could be applied to the C-H selenation of fluorine-containing aromatic compounds bearing either alkyl or aryl sulfide moieties, which could plausibly lead to the introduction of two different chalcogen atoms on tetrafluorobenzene derivatives.

phosphorus, sulfur, and silicon and the related elements

Iodine-promoted C-H sulfidation of electron-deficient fluorine-containing arenes with thiols or diselenides leading to unsymmetrical introduction of sulfide or selenide moieties onto tetrafluorobenzene