Disulfide-Directed C-H Hydroxylation for Synthesis of Sulfonyl Diphenyl Sulfides and 2-(Phenylthio)phenols with Oxygen as Oxidant.

Compared to N, O and P as directing functional atoms, the application of directing group containing sulfur atoms for transition metal-catalyzed C-H activation is much more difficult for the known reason (some metal catalysts are easily poisoned by sulfur). Here, the disulfide-directed C-H activation for thew synthesis of sulfonyl diphenyl sulfides was realized for the first time by a copper-catalyzed, tandem, one-step C-S coupling/hydroxylation of disulfides and arylboronic acids with oxygen as the oxidant. This method provides a mild and easy method for the synthesis of sulfonyl diphenyl sulfides and 2-(phenylthio)phenol derivatives and avoids producing sulfoxides and sulfones under air conditions and elevated temperatures. [ABSTRACT FROM AUTHOR]