Indium(I) Iodide-Mediated Regioselective Ring Opening of Epoxides with Diphenyldiselenide: The Preparation of β-Hydroxy Selenides

Epoxides were efficiently transformed into β-hydroxy selenides by the action of diphenyldiselenide and indium(I) iodide under mild conditions. The ring opening reaction is regioselective with nucleophile incorporation at the less hindered carbon atom for alkyl-substituted epoxides, and at the benzylic carbon atom for aryl derivatives.