Simple cleavage of diorganyl diselenides with NaBH4/PEG-400 and direct Michael addition to electron-deficient alkenes

Nucleophilic species of selenium were generated in situ from the reaction of diorganyl diselenide with NaBH4 in PEG-400 as solvent and selectively added to several α,β-unsaturated ketones, esters, acid, and nitrile. By this simple procedure, chalcogenolate anions were directly added at mild conditions, furnishing the respective Michael adducts in good yields.