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

被引：22
|
作者：
Perin, Gelson [1 ]
Borges, Elton L. [1 ]
Rosa, Paloma C. [1 ]
Carvalho, Patrick N. [1 ]
Lenardao, Eder J. [1 ]
机构：
[1] Univ Fed Pelotas, UFPel, CCQFA, LASOL, BR-96010900 Pelotas, RS, Brazil
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 13期
关键词：
Organoselenium compounds; PEG-400; beta-Phenylselanylcarbonyl compounds; Michael adduct; alpha; beta-Carbonyl compounds; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; SOLVENT-FREE CONDITIONS; EFFICIENT CONJUGATE ADDITION; HIGHLY EFFICIENT; ORGANOSELENIUM COMPOUNDS; REDUCTIVE CLEAVAGE; THIOLS; KETONES; WATER; BENZENESELENOL;
D O I：
10.1016/j.tetlet.2013.01.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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收藏
页码：1718 / 1721
页数：4
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