What do we know about the ionic liquid effect in catalyzed multicomponent reactions?: A critical review

被引：22
作者：
Neto, Brenno A. D. [1 ]
Rocha, Rafael O. [1 ]
Lapis, Alexandre A. M. [2 ]
机构：
[1] Univ Brasilia, Lab Quim Med & Tecnol, Inst Quim, Campus Univ Darcy Ribeiro, BR-70904900 Brasilia, DF, Brazil
[2] Univ Fed Fronteira Sul, BR-89815899 Chapeco, SC, Brazil
来源：
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY | 2022年 / 35卷
关键词：
Multicomponent reactions (MCRs); Ionic liquids (ILs); Mechanism; Catalysis; Enantioselective; ONE-POT SYNTHESIS; BIGINELLI REACTION; SOLVENT-FREE; EFFICIENT SYNTHESIS; BRONSTED ACID; MECHANISM; GREEN; DERIVATIVES; SCAFFOLDS; INSIGHT;
D O I：
10.1016/j.cogsc.2022.100608
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Several multicomponent reactions (MCRs) have been conducted with improved yields and selectivities when ionic liquids (ILs) were applied as the catalysts or reaction media, as will be presented and discussed in this tutorial review. The current review also presents the importance of the IL effect in catalyzed MCRs. The effect of ion-pairing formation of large supramolecular aggregates, as well as their influences on the outcome of MCRs, are analyzed. Far beyond a reaction media of "innocent " ionic components, ILs are capable of aiding in the formation, stabilization and to improve the reactivity of reagents and intermediates during a multicomponent transformation. The origin of these positive effects relies on a combined action of cations and anions during the reaction. Although enantioselective MCRs are rarely carried out in ILs, they are also presented and critically analyzed.
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页数：14
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共 70 条
[1]   A Highly Enantioselective and Efficient Synthesis of New Pyrimidine-Fused Spiro[indoline-3,4′-pyran]s Promoted by a Novel Chiral Ionic Liquid [J].
Ahmadkhani, Amin ;
Rad-Moghadam, Kurosh ;
Roudsari, Saeedeh Toorchi .
CHEMISTRYSELECT, 2019, 4 (35) :10442-10446
[2]   Combined Role of the Asymmetric Counteranion-Directed Catalysis (ACDC) and Ionic Liquid Effect for the Enantioselective Biginelli Multicomponent Reaction [J].
Alvim, Haline G. O. ;
Pinheiro, Danielle L. J. ;
Carvalho-Silva, Valter H. ;
Fioramonte, Mariana ;
Gozzo, Fabio C. ;
da Silva, Wender A. ;
Amarante, Giovanni W. ;
Neto, Brenno A. D. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19) :12143-12153
[3]   Heteropolyacid-Containing Ionic Liquid-Catalyzed Multicomponent Synthesis of Bridgehead Nitrogen Heterocycles: Mechanisms and Mitochondrial Staining [J].
Alvim, Haline G. O. ;
Correa, Jose R. ;
Assumpcao, Jose A. F. ;
da Silva, Wender A. ;
Rodrigues, Marcelo O. ;
de Macedo, Julio L. ;
Fioramonte, Mariana ;
Gozzo, Fabio C. ;
Gatto, Claudia C. ;
Neto, Brenno A. D. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07) :4044-4053
[4]   Task-specific ionic liquid incorporating anionic heteropolyacid-catalyzed Hantzsch and Mannich multicomponent reactions. Ionic liquid effect probed by ESI-MS(/MS) [J].
Alvim, Haline G. O. ;
Bataglion, Giovana A. ;
Ramos, Luciana M. ;
de Oliveira, Aline L. ;
de Oliveira, Heibbe C. B. ;
Eberlin, Marcos N. ;
de Macedo, Julio L. ;
da Silva, Wender A. ;
Neto, Brenno A. D. .
TETRAHEDRON, 2014, 70 (20) :3306-3313
[5]   Facts, Presumptions, and Myths on the Solvent-Free and Catalyst-Free Biginelli Reaction. What is Catalysis for? [J].
Alvim, Haline G. O. ;
Lima, Tatiani B. ;
de Oliveira, Aline L. ;
de Oliveira, Heibbe C. B. ;
Silva, Fabricio M. ;
Gozzo, Fabio C. ;
Souza, Roberto Y. ;
da Silva, Wender A. ;
Neto, Brenno A. D. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08) :3383-3397
[6]   Ionic Liquid Effect over the Biginelli Reaction under Homogeneous and Heterogeneous Catalysis [J].
Alvim, Haline G. O. ;
de Lima, Tatiani B. ;
de Oliveira, Heibbe C. B. ;
Gozzo, Fabio C. ;
de Macedo, Julio L. ;
Abdenur, Patricia V. ;
Silva, Wender A. ;
Neto, Brenno A. D. .
ACS CATALYSIS, 2013, 3 (07) :1420-1430
[7]   Recent Advances in Asymmetric Counteranion-directed Catalysis (ACDC) [J].
Avila, Eloah P. ;
Amarante, Giovanni W. .
CHEMCATCHEM, 2012, 4 (11) :1713-1721
[8]   Ionic liquid-assisted refinery processes-A review and industrial perspective [J].
Ben Salah, Haifa ;
Nancarrow, Paul ;
Al-Othman, Amani .
FUEL, 2021, 302
[9]   Development of cation/anion "interaction" scales for ionic liquids through ESI-MS measurements [J].
Bini, Riccardo ;
Bortolini, Olga ;
Chiappe, Cinzia ;
Pieraccini, Daniela ;
Siciliano, Tiziana .
JOURNAL OF PHYSICAL CHEMISTRY B, 2007, 111 (03) :598-604
[10]   Deep Eutectic Solvents and Multicomponent Reactions: Two Convergent Items to Green Chemistry Strategies [J].
Calvo-Flores, Francisco G. ;
Mingorance-Sanchez, Cristina .
CHEMISTRYOPEN, 2021, 10 (08) :815-829
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