Conditions-driven selective synthesis of selenides and selenols from elemental selenium

Sodium borohydride in DMF is able to reduce elemental selenium in the presence of ethanol. Alkylation of the species resulting from the reaction of 2:1 molar equivalents of NaBH/Se allows the selective synthesis, under very mild conditions, of symmetrical dialkyl selenides. Addition of formic acid, prior to that of the electrophile, permits the synthesis of the corresponding selenols.