Aerobic Copper(II)-catalyzed synthesis of β-hydroxysulfides and selenides from alkenes with disulfides and diselenides

A copper-catalyzed hydroxysulfenylation of alkenes was achieved using disulfides in the presence of n-Bu4NI and H2O. The procedure smoothly proceeded under air atmosphere, and the corresponding beta-hydroxysulfides were obtained with regio- and anti-selectivity in good yields. Furthermore, a reaction using diselenides effectively produced the expected beta-hydroxyselenides. These reactions could use both chalcogenide groups on dichalcogenides. Further the procedure also worked for hydrosulfenylation using thiols. (C) 2022 Elsevier Ltd. All rights reserved.

Automated summary

A copper-catalyzed hydroxysulfenylation of alkenes using disulfides in the presence of n-Bu4NI and H2O is reported in this article. The reaction proceeded smoothly under air atmosphere and resulted in good yields of β-hydroxysulfides with regio- and anti-selectivity. Additionally, the reaction using diselenides also provided the desired β-hydroxyselenides effectively. The chalcogenide groups on dichalcogenides were utilized in these reactions. Furthermore, the procedure was successful for hydrosulfenylation using thiols.