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

[1] Design and Synthesis of Bis Thiazol-2-ylidenes
Sravanthi, T. V.
Pottem, Madhusudhana Reddy
Manju, S. L.
ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (10) : 5370 - 5372
[2] On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis
Delfau, Ludivine
Assani, Nadhrata
Nichilo, Samantha
Pecaut, Jacques
Philouze, Christian
Broggi, Julie
Martin, David
Tomas-Mendivil, Eder
ACS ORGANIC & INORGANIC AU, 2023, 3 (03): : 136 - 142
[3] Considerations regarding the polarity reversal in electrochemically generated hypochlorite
Ciobotaru, I.E. (irinaelenaciobotaru@yahoo.com), 1600, National Institute of Optoelectronics (16): : 1 - 2
[4] Considerations regarding the polarity reversal in electrochemically generated hypochlorite
Ciobotaru, I. E.
Vaireanu, D. I.
JOURNAL OF OPTOELECTRONICS AND ADVANCED MATERIALS, 2014, 16 (1-2): : 198 - 206
[5] Thiazol-2-ylidenes as N-Heterocyclic carbene ligands with enhanced electrophilicity for transition metal catalysis
Zhang, Jin
Li, Tao
Li, Xiangyang
Lv, Anqi
Li, Xue
Wang, Zheng
Wang, Ruihong
Ma, Yangmin
Fang, Ran
Szostak, Roman
Szostak, Michal
COMMUNICATIONS CHEMISTRY, 2022, 5 (01)
[6] Thiazol-2-ylidenes as N-Heterocyclic carbene ligands with enhanced electrophilicity for transition metal catalysis
Jin Zhang
Tao Li
Xiangyang Li
Anqi Lv
Xue Li
Zheng Wang
Ruihong Wang
Yangmin Ma
Ran Fang
Roman Szostak
Michal Szostak
Communications Chemistry, 5
[7] Copper(I)-Thiazol-2-ylidenes: Highly Reactive N-Heterocyclic Carbenes for the Hydroboration of Terminal and Internal Alkynes. Ligand Development, Synthetic Utility, and Mechanistic Studies
Zhang, Jin
Li, Xue
Li, Tao
Zhang, Gaopeng
Wan, Kerou
Ma, Yangmin
Fang, Ran
Szostak, Roman
Szostak, Michal
ACS CATALYSIS, 2022, 12 (24) : 15323 - 15333
[8] Electrochemically induced in-situ generated Co(OH)2 nanoplates to promote the Volmer process toward efficient alkaline hydrogen evolution reaction
Jiang, Li-Wen
Huang, Yuan
Chen, Bing-Bing
Zhou, Jian-Qiu
Liu, Hong
Wang, Jian-Jun
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, 2021, 46 (12) : 8497 - 8506
[9] ELECTROSYNTHESES BASED ON REACTIONS OF ADDITION OF ELECTROCHEMICALLY GENERATED RADICALS TO ETHYLENE AND ITS DERIVATIVES .2. MECHANISM OF THE REACTION
VASSILIEV, YB
BAGOTZKY, VS
KOVSMAN, EP
GRINBERG, VA
KANEVSKY, LS
POLISHCHYUK, VR
ELECTROCHIMICA ACTA, 1982, 27 (07) : 929 - 936
[10] Intermolecular Stetter reaction of aromatic aldehydes with(E)-(2-nitrovinyl)cyclohexane induced by N-heterocyclic carbene and thiourea
Qing-Fang Cheng
Jing-Wen Wang
Qi-Fa Wang
Zhou Liu
ChineseChemicalLetters, 2016, 27 (07) : 1032 - 1035

← 1 2 3 →