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

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

“…Looking at the capability of molecular iodine in the cleavage of sulphur-sulphur bond in their past work, Sakai and co-workers achieved the reaction of sulfidation of perfluoroarenes using molecular iodine as catalyst and a base in the presence of DMSO acting as the solvent medium for this strategy (Scheme 11 (b)). [135] This group has used benzenethiol derivatives where they found that a similar transformation occured even in the case of diphenylsilanes. The formation of desired products is not observed, when base is absent in the standard conditions; while changes of solvent lead to almost negligible amounts of product or no product formation at all.…”

“…All these methods have a limited substrate scope and some of them are incapable of producing unsymmetrical desired products. Looking at the capability of molecular iodine in the cleavage of sulphur‐sulphur bond in their past work, Sakai and co‐workers achieved the reaction of sulfidation of perfluoroarenes using molecular iodine as catalyst and a base in the presence of DMSO acting as the solvent medium for this strategy (Scheme 11 (b)) [135] . This group has used benzenethiol derivatives where they found that a similar transformation occured even in the case of diphenylsilanes.…”