Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: The Stetter reaction

被引：18

作者：

Orsini, Monica ^{[1
]}

Chiarotto, Isabella ^{[2
]}

Sotgiu, Giovanni ^{[1
]}

Inesi, Achille ^{[2
]}

机构：

[1] Univ Roma Tre, Dip Elettron Applicata, I-00146 Rome, Italy

[2] Univ Roma La Sapienza, Dip Ingn Chim Mat Ambiente, I-00161 Rome, Italy

来源：

ELECTROCHIMICA ACTA | 2010年 / 55卷 / 10期

关键词：

N-Heterocyclic carbene; Thiazolium salt; Electrochemical reduction; Stetter reaction; N-HETEROCYCLIC CARBENES; TEMPERATURE IONIC LIQUIDS; IMIDAZOL-2-YLIDENES; 1,4-DIKETONES; INHIBITORS; REDUCTION;

D O I：

10.1016/j.electacta.2010.01.082

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

The inversion of the normal reactivity (umpolung) of aldehydes has been induced via N-heterocyclic carbenes (NHCs) thiazol-2-ylidenes 2a or 3a, generated by simple electrolyses of solutions containing thiazolium salt 2 or 3. Accordingly, 1,4-dicarbonyl compounds have been obtained, in mild conditions and in moderate to very high yields, via 1,4-addition of the Breslow intermediates to the suitable Michael acceptor. The procedure has been performed in classical organic solvents (VOCs) as well as in room temperature ionic liquids (RTILs). The different reactivity of aliphatic aldehydes vs the one of aromatic and heteroaromatic aldehydes has been emphasized. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3511 / 3517

页数：7

共 29 条

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