An (NH4)2S2O8-promoted cross-coupling of thiols/diselenides and sulfoxides for the synthesis of unsymmetrical disulfides/selenosulfides

An (NH4)(2)S2O8-promoted cross-coupling of thiols/diselenides and sulfoxides to construct unsymmetrical disulfides/selenosulfides is disclosed. Control experiments demonstrate that (NH4)(2)S2O8 acts as an acid and an oxidant, while both ionic and radical routes are involved in the reaction. The KIE experiments reveal that C-H bond cleavage of sulfoxides was involved in the turnover-limiting step.

Automated summary

This study presents the (NH4)(2)S2O8-promoted cross-coupling reaction of thiols/diselenides and sulfoxides to form unsymmetrical disulfides/selenosulfides. Control experiments demonstrate that (NH4)(2)S2O8 acts as both an acid and an oxidant, and the reaction involves both ionic and radical routes. Kinetic isotope effect experiments reveal that the C-H bond cleavage of sulfoxides is involved in the rate-limiting step.