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 alpha,beta-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. (C) 2013 Elsevier Ltd. All rights reserved.