scholarly journals Ionic Liquid-Assisted Grinding: An Electrophilic Fluorination Benchmark

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5756
Author(s):  
Pavel A. Zaikin ◽  
Ok Ton Dyan ◽  
Innokenty R. Elanov ◽  
Gennady I. Borodkin
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Vacuum Sublimation ◽  
Dicarbonyl Compounds ◽  
Careful Choice ◽  
Electrophilic Fluorination ◽  
Lower Viscosity ◽  
Speed Up ◽  
High Yields ◽  
Molecular Solvents

We demonstrated the influence of liquid additives on the rate and selectivity of mechanochemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichiometric catalytic quantities of ionic liquids speed up the reaction. We proposed an improved protocol for ionic liquids-assisted fluorination that allows easy and efficient isolation of fluorinated products by vacuum sublimation. A careful choice of additive results in high yields of fluorinated products and low E-factor for the overall process. Here, we report a benchmarking study of various ionic liquids in comparison with representative molecular solvents. A lower viscosity of ionic liquid additive is typically associated with higher yields and a higher degree of difluorination. Ionic liquids with fluorous anions (triflate and triflimide) are shown to be the most efficient catalysts for ionic liquid-assisted grinding.

One Pot Three Component Synthesis of 9-arylpolyhydroacridine Derivatives in an Ionic Liquid Medium

2005 ◽  
Vol 2005 (9) ◽  
pp. 600-602 ◽  
Author(s):  
Yu-Ling Li ◽  
Mei-Mei Zhang ◽  
Xiang-Shan Wang ◽  
Da-Qing Shi ◽  
Shu-Jiang Tu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields ◽  
Work Up ◽  
Ionic Liquid Medium

In this paper the preparation of 3,3,6,6-tetramethyl-9-aryl-1,2,3,4,5,6,7,8,9,10- decahydroacridin-1,8-dione derivatives from aromatic aldehydes, 5,5-dimethyl-1,3- cyclohexanedione and ammonium acetate in ionic liquids [bmim+][BF4-] is described. This new method has the advantages of easier work-up, milder reaction conditions, high yields and an environmentally benign procedure compared with other methods.

Plasmonic behavior of ionic liquid stabilized gold nanoparticles in molecular solvents

2017 ◽  
Vol 41 (21) ◽  
pp. 12989-12995 ◽  
Author(s):  
Sachin Thawarkar ◽  
Balu Thombare ◽  
Nageshwar D. Khupse
Keyword(s):  
Gold Nanoparticles ◽  
Ionic Liquid ◽  
Ionic Liquids ◽  
Surface Plasmon Resonance ◽  
Dielectric Properties ◽  
Surface Plasmon ◽  
Plasmon Resonance ◽  
Facile Synthesis ◽  
Imidazolium Ionic Liquids ◽  
Molecular Solvents

In this paper, we have demonstrated the facile synthesis of stable gold nanoparticles (AuNPs) using imidazolium ionic liquids (ImILs) as a stabilizer as well as a surfactant and their surface plasmon resonance (SPR) in different molecular solvents with varying dielectric properties.

A Phosphine-mediated Synthesis of 2,3,4,5-tetra-substituted Nhydroxypyrroles from α-oximino Ketones and Dialkyl Acetylenedicarboxylates Under Ionic Liquid Green-media

2018 ◽  
Vol 21 (1) ◽  
pp. 14-18
Author(s):  
Ashraf S. Shahvelayati ◽  
Maryam Ghazvini ◽  
Khadijeh Yadollahzadeh ◽  
Akram S. Delbari
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Organic Solvents ◽  
Condensation Reaction ◽  
Reaction Medium ◽  
Sustainable Chemistry ◽  
Polyfunctional Compounds ◽  
High Yields ◽  
Work Up ◽  
Reaction Media

Background: The development of multicomponent reactions (MCRs) in the presence of task-specific ionic liquids (ILs), used not only as environmentally benign reaction media, but also as catalysts, is a new approach that meet with the requirements of sustainable chemistry. In recent years, the use of ionic liquids as a green media for organic synthesis has become a chief study area. This is due to their unique properties such as non-volatility, non-flammability, chemical and thermal stability, immiscibility with both organic compounds and water and recyclability. Ionic liquids are used as environmentally friendly solvents instead of hazardous organic solvents. Objective: We report the condensation reaction between α-oximinoketone and dialkyl acetylene dicarboxylate in the presence of triphenylphosphine to afford substituted pyrroles under ionic liquid conditions in good yields. Result: Densely functionalized pyrroles was easily prepared from reaction of α-oximinoketones, dialkyl acetylene dicarboxylate in the presence of triphenylphosphine in a quantitative yield under ionic liquid conditions at room temperature. Conclusion: In conclusion, ionic liquids are indicated as a useful and novel reaction medium for the selective synthesis of functionalized pyrroles. This reaction medium can replace the use of hazardous organic solvents. Easy work-up, synthesis of polyfunctional compounds, decreased reaction time, having easily available-recyclable ionic liquids, and good to high yields are advantages of present method.

Towards solvent-controlled reactivity in ionic liquids

2013 ◽  
Vol 85 (10) ◽  
pp. 1979-1990 ◽  
Author(s):  
Hon Man Yau ◽  
Sinead T. Keaveney ◽  
Bradley J. Butler ◽  
Eden E. L. Tanner ◽  
Max S. Guerry ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Mole Fraction ◽  
Reaction Coordinate ◽  
Ionic Solvent ◽  
Molecular Solvents

Ionic liquids are frequently touted as alternatives to traditional molecular solvents but are limited in their applicability as the outcome of reactions may be altered on moving from a molecular to an ionic solvent. This manuscript summarizes our progress towards a predictive framework through understanding how ionic solvents affect organic processes, with an emphasis on how these findings might be applied. Particularly, we will consider the importance of the mole fraction of the ionic liquid used, including some hitherto undisclosed results, as well as the importance of understanding the key interactions of the solvent with the components along the reaction coordinate.

Promotional effect of ionic liquids in electrophilic fluorination of methylated uracils

RSC Advances ◽  
2016 ◽  
Vol 6 (65) ◽  
pp. 60556-60564 ◽  
Author(s):  
Gennady I. Borodkin ◽  
Innokenty R. Elanov ◽  
Yury V. Gatilov ◽  
Vyacheslav G. Shubin
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Electrophilic Fluorination ◽  
Promotional Effect

The use of a small amount of ionic liquid as an additive results in acceleration of the fluorination of 6-methyluracil and 1,3,6-trimethyluracil with Selectfluor™ in MeOH and EtOH.

Ionic liquid solvents: the importance of microscopic interactions in predicting organic reaction outcomes

2017 ◽  
Vol 89 (6) ◽  
pp. 745-757 ◽  
Author(s):  
Sinead T. Keaveney ◽  
Ronald S. Haines ◽  
Jason B. Harper
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Transition State ◽  
Physical Properties ◽  
Solvent Effects ◽  
Recent Progress ◽  
Comprehensive Understanding ◽  
Organic Reaction ◽  
Microscopic Interactions ◽  
Molecular Solvents

AbstractIonic liquids are attractive alternatives to molecular solvents as they have many favourable physical properties and can produce different organic reaction outcomes compared to molecular solvents. Thus far, interactions between the ionic liquid components and specific sites (such as charged centres, lone pairs and π systems) on the reagents and transition state have been identified as affecting reaction outcome; a comprehensive understanding of these interactions is necessary to allow prediction of ionic liquid solvent effects. This manuscript summarises our recent progress in the development of a framework for predicting the effect of an ionic liquid solvent on the outcome of organic processes. There will be a particular focus on the importance of the different interactions between the ionic liquid components and the species along the reaction coordinate that are responsible for the changes in reaction outcome observed in the cases described.

Efficient regio- and stereo-selective cleavage of aziridines and epoxides using an ionic liquid as reagent and reaction medium

2007 ◽  
Vol 85 (5) ◽  
pp. 366-371 ◽  
Author(s):  
Brindaban C Ranu ◽  
Laksmikanta Adak ◽  
Subhash Banerjee
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Organic Solvent ◽  
Reaction Medium ◽  
Synthetic Route ◽  
High Yields

Ionic liquids, containing a variety of functionalities such as halo, azido, and thiocyano, efficiently cleave aziridines and epoxides to the corresponding products in high yields. The cleavages are regio- and stereo-selective. The reactions are complete in 1 h at 60 °C and do not require any other catalyst or organic solvent. Thus, a convenient synthetic route to 1,2-haloamines, 1,2-azidoamines, 1,2-thiocyanoamines, 1,2-azidoalcohols, and 1,2-thiocyanoalcohols is developed.Key words: aziridine, epoxide, ionic liquid, cleavage, regioselectivity, stereoselectivity

Organic Reactions in Ionic Liquids: α-Tosyloxylation of Ketones

2002 ◽  
Vol 2002 (12) ◽  
pp. 618-619 ◽  
Author(s):  
Yuan Yuan Xie ◽  
Zhen Chu Chen ◽  
Qin Guo Zheng
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Room Temperature Ionic Liquid ◽  
Organic Reactions ◽  
Molecular Solvents

The room temperature ionic liquid, n-butylpyridinium tetrafluoroborate (BPyBF4) is used as a “green” recyclable alternative to classical molecular solvents for the α-tosyloxylation of ketones.

scholarly journals Frustrated Lewis pairs in ionic liquids and molecular solvents – a neutron scattering and NMR study of encounter complexes

2018 ◽  
Vol 54 (63) ◽  
pp. 8689-8692 ◽  
Author(s):  
Lucy C. Brown ◽  
James M. Hogg ◽  
Mark Gilmore ◽  
Leila Moura ◽  
Silvia Imberti ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Neutron Scattering ◽  
Frustrated Lewis Pairs ◽  
Frustrated Lewis Pair ◽  
Nmr Study ◽  
Molecular Solvents ◽  
Lewis Pairs

Encounter complexes of a frustrated lewis pair are more stable and prevalent in an ionic liquid than in benzene.

Mapping the “Extra Solvent Power, ESP” of Ionic Liquids for Monomers, Polymers and Globular Nanoparticles

2017 ◽  
Author(s):  
Jose A. Pomposo
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Linear Polymers ◽  
Green Solvents ◽  
Ionic Polymers ◽  
First Time ◽  
Solvent Power

Understanding the miscibility behavior of ionic liquid (IL) / monomer, IL / polymer and IL / nanoparticle mixtures is critical for the use of ILs as green solvents in polymerization processes, and to rationalize recent observations concerning the superior solubility of some proteins in ILs when compared to standard solvents. In this work, the most relevant results obtained in terms of a three-component Flory-Huggins theory concerning the “Extra Solvent Power, ESP” of ILs when compared to traditional non-ionic solvents for monomeric solutes (case I), linear polymers (case II) and globular nanoparticles (case III) are presented. Moreover, useful ESP maps are drawn for the first time for IL mixtures corresponding to case I, II and III. Finally, a potential pathway to improve the miscibility of non-ionic polymers in ILs is also proposed.

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