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

Full Text: HTML

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.

Related Articles:

β??Cyclodextrin??Promoted Addition of Benzeneselenol to Conjugated Alkenes in Water

[Srinivas, Boga; Kumar, Vydyula Pavan; Sridhar, Regati; Reddy, Vutukuri Prakash; Nageswar, Yadavalli Venkata Durga; Rao, Kakulapati Rama Helvetica Chimica Acta, 2009 , vol. 92, # 6 p. 1080 - 1084]

Rapid and precise preparation of reactive benzeneselenolate solutions by reduction of diphenyl diselenide with hydrazine–sodium methanolate

[Henriksen, Lars; Stuhr-Hansen, Nicolai Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 14 p. 1915 - 1916]

Ultrasonic formation and reactions of sodium phenylselenide

[Ley, Steven V.; O'Neil, Ian A.; Low, Caroline M. R. Tetrahedron, 1986 , vol. 42, # 19 p. 5363 - 5368]

More Articles...