An alternative approach to selenides and diselenides from Se(0) and epoxides/aziridines under sustainable conditions

The on-water reduction of elemental selenium promoted by rongalite (sodium hydroxymethanesulfinate)/ sodium hydroxide provided selenide anions, which led to a variety of β-hydroxy and β- amino selenides upon reaction with epoxides and aziridines through an alternative and sustainable approach. The reactions are operationally simple and occur in a highly regioselective and enantioconservative way. The preparation of diselenides was also accomplished by a different approach which relies on the generation of diselenide dianions from elemental selenium and sodium borohydride. Reaction with three-membered heterocycles led to differently substituted β-hydroxy and β-amino diselenides.