Simple cleavage of diorganyl diselenides with NaBH 4/PEG-400 and direct Michael addition to electron-deficient alkenes

…, EL Borges, PC Rosa, PN Carvalho, EJ Lenardão

Index: Perin, Gelson; Borges, Elton L.; Rosa, Paloma C.; Carvalho, Patrick N.; Lenardao, Eder J. Tetrahedron Letters, 2013 , vol. 54, # 13 p. 1718 - 1721

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Citation Number: 13

Abstract

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.