scholarly journals Proline Based Chiral Ionic Liquids for Enantioselective Michael Reaction

2014 ◽  
Vol 2014 ◽  
pp. 1-9 ◽  
Author(s):  
Kaoru Nobuoka ◽  
Satoshi Kitaoka ◽  
Tsutomu Kojima ◽  
Yuuki Kawano ◽  
Kazuya Hirano ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Ionic Liquids ◽  
Positive Charge ◽  
Michael Reaction ◽  
Chiral Synthesis ◽  
Chiral Catalyst ◽  
New Approach ◽  
Chiral Ionic Liquids ◽  
Chiral Ionic Liquid

Chiral ionic liquids, starting from (S)-proline, have been prepared and evaluated the ability of a chiral catalyst. In Michael reaction of trans-β-nitrostyrene and cyclohexanone, all the reactions were carried out under homogeneous conditions without any solvent except for excess cyclohexanone. The chiral ionic liquid catalyst with the positive charge delocalized bulky pyrrolidinium cation shows excellent yields (up to 92%), diastereoselectivities (syn/anti = 96/4), and enantioselectivities (up to 95% ee) and could be reused at least three times without any loss of its catalytic activity. Such results demonstrated a promising new approach for green and economic chiral synthesis by using the chiral ionic liquids as a chiral catalyst and a chiral medium.

Tetracarboxyl-Functionalized Ionic Liquid: Synthesis and Catalytic Properties

2015 ◽  
Vol 68 (10) ◽  
pp. 1513 ◽  
Author(s):  
Miaona Feng ◽  
Guoying Zhao ◽  
Hongling Gao ◽  
Suojiang Zhang
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Ionic Liquids ◽  
Propionic Acid ◽  
Propylene Carbonate ◽  
Propylene Oxide ◽  
High Stability ◽  
Ammonium Acetate ◽  
Catalytic Properties ◽  
Potential Applications

Novel tetracarboxyl-functionalized 2,2′-biimidazolium-based ionic liquids (ILs) with different anions were synthesized in two steps from readily available and sustainable starting materials including ammonium acetate, glyoxal, and halogenated propionic acid. The functionalized IL exhibited higher catalytic activity towards the cycloaddition of CO2 to terminal epoxides. With propylene oxide as a substrate, the optimum yield of propylene carbonate reached 82.7 % at an initial CO2 pressure of 2.0 MPa for 4 h at 140°C. Moreover, the functionalized IL catalyst displayed a high stability and can be reused for at least five cycles without obvious loss of catalytic activity. The results provide a simple and economical way to synthesize multi-functionalized imidazolium-based ILs with versatile potential applications.

scholarly journals The effect of the morpholinium ionic liquid anion on the catalytic activity of Rh (or Pt) complex–ionic liquid systems in hydrosilylation processes

RSC Advances ◽  
2018 ◽  
Vol 8 (47) ◽  
pp. 26922-26927 ◽  
Author(s):  
Magdalena Jankowska-Wajda ◽  
Izabela Dąbek ◽  
Ryszard Fiedorow ◽  
Hieronim Maciejewski
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Ionic Liquids ◽  
Platinum Complexes ◽  
Pt Complex ◽  
Liquid Systems

Rhodium and platinum complexes were immobilized in morpholinium ionic liquids, the effect of which on the catalytic activity was determined.

scholarly journals Beneficial Contribution of Biosourced Ionic Liquids and Microwaves in the Michael Reaction

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 814
Author(s):  
Katia Bacha ◽  
Kawther Aguibi ◽  
Jean-Pierre Mbakidi ◽  
Sandrine Bouquillon
Keyword(s):  
Ionic Liquids ◽  
Reaction Time ◽  
Michael Reaction ◽  
Chiral Ionic Liquids ◽  
Michael Reactions ◽  
Basic Catalysts ◽  
The Michael Reaction

We developed a synthesis of chiral ionic liquids from proline and one of its derivatives. Nine chiral ionic liquids were synthesized with yields from 78% to 95%. These synthesized ionic liquids played two roles in Michael reactions, as solvents, and as basic catalysts, where the ionic phase could also be reused at least five times without loss of activity. The yields up to 99% were improved by increasing the amount of dimethylmalonate from 1.2 equivalents to 3 or 4 equivalents. Furthermore, the reaction time could be reduced from 24 h to 45 min through microwaves activation.

scholarly journals Synthesis of chiral ionic liquids by ion cross-metathesis: en route to enantioselective water–ionic liquid extraction (EWILE), an eco-friendly variant of the ELLE process

2012 ◽  
Vol 48 (26) ◽  
pp. 3185 ◽  
Author(s):  
Viacheslav Zgonnik ◽  
Chantal Zedde ◽  
Yves Génisson ◽  
Marie-Rose Mazières ◽  
Jean-Christophe Plaquevent
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Liquid Extraction ◽  
Chiral Ionic Liquids ◽  
Cross Metathesis

Tailoring ionic liquid catalysts: structure, acidity and catalytic activity of protonic ionic liquids based on anionic clusters, [(HSO4)(H2SO4)x]− (x = 0, 1, or 2)

2014 ◽  
Vol 16 (7) ◽  
pp. 3463-3471 ◽  
Author(s):  
Karolina Matuszek ◽  
Anna Chrobok ◽  
Fergal Coleman ◽  
Kenneth R. Seddon ◽  
Małgorzata Swadźba-Kwaśny
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Ionic Liquids ◽  
Chemical Properties ◽  
Esterification Reaction ◽  
Anionic Clusters ◽  
Physico Chemical

The speciation of a family of inexpensive, easily prepared protonic ionic liquids, their physico-chemical properties and their performance as catalysts in the model esterification reaction have been correlated.

Understanding the role of hydrogen bonding in Brønsted acidic ionic liquid-catalyzed transesterification: a combined theoretical and experimental investigation

2016 ◽  
Vol 18 (48) ◽  
pp. 32723-32734 ◽  
Author(s):  
Kaixin Li ◽  
Yibo Yan ◽  
Jun Zhao ◽  
Junxi Lei ◽  
Xinli Jia ◽  
...  
Keyword(s):  
Experimental Investigation ◽  
Ionic Liquid ◽  
Hydrogen Bonding ◽  
Catalytic Activity ◽  
Ionic Liquids ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Acidic Ionic Liquids ◽  
Hydrogen Bonding Networks

The intra- and inter-hydrogen bonding networks that govern the catalytic activity of Brønsted acidic ionic liquids were identified.

Asymmetric Michael Reaction Catalyzed by Chiral Ionic Liquids

Synfacts ◽  
2006 ◽  
Vol 2006 (6) ◽  
pp. 0611-0611
Author(s):  
S. Luo ◽  
J.-P. Cheng ◽  
X. Mi ◽  
L. Zhang ◽  
S. Liu ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Michael Reaction ◽  
Chiral Ionic Liquids ◽  
Asymmetric Michael Reaction

ChemInform Abstract: Synthesis of Chiral Ionic Liquids by Ion Cross-Metathesis: en route to Enantioselective Water-Ionic Liquid Extraction (EWILE), an Eco-Friendly Variant of the ELLE Process.

ChemInform ◽  
2012 ◽  
Vol 43 (30) ◽  
pp. no-no
Author(s):  
Viacheslav Zgonnik ◽  
Chantal Zedde ◽  
Yves Genisson ◽  
Marie-Rose Mazieres ◽  
Jean-Christophe Plaquevent
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Liquid Extraction ◽  
Chiral Ionic Liquids ◽  
Cross Metathesis

An Efficient and Ecofriendly Three-Component Reaction for the Rapid Synthesis of 2-Amino-4H-chromenes Catalyzed by a DABCO­-Based Ionic Liquid

Synthesis ◽  
2018 ◽  
Vol 50 (18) ◽  
pp. 3708-3714 ◽  
Author(s):  
Da-Zhen Xu ◽  
Cheng-Bin Li ◽  
Yu-Wei Li
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Michael Reaction ◽  
Reaction Times ◽  
Rapid Synthesis ◽  
Biologically Relevant ◽  
Mild Conditions ◽  
Three Component Reaction ◽  
Green Strategy

An efficient, economical, and green strategy for the construction of biologically relevant 2-amino-4H-chromene scaffolds via a tandem Knoevenagel–Pinner cyclization–Michael reaction has been successfully developed. In the presence of DABCO-based ionic liquids, two different 2-amino-4H-chromene derivatives, 2-amino-4-(indol-3-yl)-4H-chromenes and 2-amino-4-(pyrazol-4-yl)-4H-chromenes, were prepared in good to excellent yields (81–97%) within short reaction times under mild conditions. All the products are purified by simple crystallization. The catalyst could be recycled for at least five times.

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