The double role of ionic liquids in organic electrosynthesis: Precursors of N-heterocyclic carbenes and green solvents. Henry reaction

被引：31
|
作者：
Feroci, Marta [1 ]
Elinson, Mikhail N. [2 ]
Rossi, Leucio [3 ]
Inesi, Achille [1 ]
机构：
[1] Univ Roma La Sapienza, Dip Ingn Chim Mat Ambiente, I-00161 Rome, Italy
[2] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia
[3] Univ Studi, Dipartimento Chim Ingn Chim & Mat, I-67040 Laquila, Italy
来源：
ELECTROCHEMISTRY COMMUNICATIONS | 2009年 / 11卷 / 07期
关键词：
Henry reaction; N-heterocyclic carbenes; Electrosynthesis; Ionic liquids; CATALYST;
D O I：
10.1016/j.elecom.2009.05.045
中图分类号：
O646 [电化学、电解、磁化学];
学科分类号：
081704 ;
摘要：
N-heterocyclic carbenes, electrogenerated by cathodic reduction of imidazolium-based room temperature ionic liquids (RTILs), are stable bases able to catalyze the Henry reaction. Accordingly, the electrosynthesis of beta-nitroalcohols has been achieved, under mild conditions and in high yields, by stirring nitromethane and aldehydes in previously electrolyzed RTILs. RTILs have been used as green solvents as well as precursors of N-heterocyclic carbenes. (c) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码：1523 / 1526
页数：4
相关论文
共 30 条
  • [21] Free N-heterocyclic carbenes from Bronsted acidic ionic liquids: Direct detection by electrospray ionization mass spectrometry
    Salvitti, Chiara
    Pepi, Federico
    Manago, Marta
    Bortolami, Martina
    Michenzi, Cinzia
    Chiarotto, Isabella
    Troiani, Anna
    de Petris, Giulia
    RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2022, 36 (17)
  • [22] Diethanolamine and N,N-diethylethanolamine ionic liquids as precatalyst-precursors and reaction media in green Heck reaction protocol
    Petrovic, Zorica D.
    Simijonovic, Dusica
    Petrovic, Vladimir P.
    Markovic, Svetlana
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 327 (1-2) : 45 - 50
  • [23] Ionic liquids: green solvents and reactive compounds? Reaction of tri-n-butylmethylphosphonium dimethylphosphate with elemental sulfur
    Tarasova, Natalia
    Krivoborodov, Efrem
    Zanin, Alexey
    Mezhuev, Yaroslav
    PURE AND APPLIED CHEMISTRY, 2021, 93 (01) : 29 - 37
  • [24] First direct evidence of N-heterocyclic carbene in BMIm acetate ionic liquids. An electrochemical and chemical study on the role of temperature
    Chiarotto, I.
    Feroci, M.
    Inesi, A.
    NEW JOURNAL OF CHEMISTRY, 2017, 41 (16) : 7840 - 7843
  • [25] Reaction of Pyridine-N-Oxides with Tertiary sp2-N-Nucleophiles: An Efficient Synthesis of Precursors for N-(Pyrid-2-yl)-Substituted N-Heterocyclic Carbenes
    Bugaenko, Dmitry, I
    Yurovskaya, Marina A.
    Karchava, Alexander, V
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (24) : 5777 - 5782
  • [26] Improvement of CO2 capture processes by tailoring the reaction enthalpy of Aprotic N-Heterocyclic anion-based ionic liquids
    Hospital-Benito, D.
    Lemus, J.
    Moya, C.
    Santiago, R.
    Palomar, J.
    CHEMICAL ENGINEERING JOURNAL ADVANCES, 2022, 10
  • [27] Imidazolium-Based Poly(Ionic Liquid)s Featuring Acetate Counter Anions: Thermally Latent and Recyclable Precursors of Polymer-Supported N-Heterocyclic Carbenes for Organocatalysis
    Lambert, Romain
    Coupillaud, Paul
    Wirotius, Anne-Laure
    Vignolle, Joan
    Taton, Daniel
    MACROMOLECULAR RAPID COMMUNICATIONS, 2016, 37 (14) : 1143 - 1149
  • [28] Reactivity of electrogenerated N-heterocyclic carbenes in room-temperature ionic liquids.: Cyclization to 2-azetidinone ring via C-3/C-4 bond formation
    Feroci, Marta
    Chiarotto, Isabella
    Orsini, Monica
    Sotgiu, Giovanni
    Inesi, Achille
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1355 - 1359
  • [29] Synthesis of Well-Defined Copper N-Heterocyclic Carbene Complexes and Their Use as Catalysts for a "Click Reaction": A Multistep Experiment That Emphasizes the Role of Catalysis in Green Chemistry
    Ison, Elon A.
    Ison, Ana
    JOURNAL OF CHEMICAL EDUCATION, 2012, 89 (12) : 1575 - 1577
  • [30] Propargyl amines by aldehyde-amine-acetylene coupling mediated by Ag(I) and Cu(I) complexes of super bulky N-heterocyclic carbenes: Unveiling the role of the super bulky ligands in the coupling reaction
    Manne, Rajesh
    Sharma, Sunita
    Dey, Shreyata
    Patil, Sagar K.
    Nehra, Nidhi
    Rawool, Hemant
    Rajaraman, Gopalan
    Ghosh, Prasenjit
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1316
123