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 conditio...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2013-03, Vol.54 (13), p.1718-1721
Main Authors: Perin, Gelson, Borges, Elton L., Rosa, Paloma C., Carvalho, Patrick N., Lenardão, Eder J.
Format: Article
Language:English
Subjects:
Alkenes
Cleavage
Esters
Ketones
Michael adduct
Michael reaction
Nitriles
Organoselenium compounds
PEG-400
Solvents
Tetrahedrons
α,β-Carbonyl compounds
β-Phenylselanylcarbonyl compounds
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.01.071