Synthesis of Novel Chiral Ionic Liquids Based on (−)-Menthyl Isonicotinate

Abstract

Thirteen novel chiral ionic liquids (CILs) containing the (?)-menthyl group can be easily prepared from isonicotinic acid with yields of 35–90%. The properties and characterization of these compounds were discussed and the alternation of optical rotation was analyzed.     

Metal Sulfide Nanoparticle Synthesis with Ionic Liquids – State of the Art and Future Perspectives

Metal sulfides are among the most promising materials for a wide variety of technologically relevant applications ranging from energy to environment and beyond. Incidentally, ionic liquids (ILs) have been among the top research subjects for the same applications and also for inorganic materials synthesis. As a result, the exploitation of the peculiar properties of ILs for metal sulfide synthesis could provide attractive new avenues for the generation of new, highly specific metal sulfides for numerous applications. This article therefore describes current developments in metal sulfide nanoparticle synthesis as exemplified by a number of highlight examples. Moreover, the article demonstrates how ILs have been used in metal sulfide synthesis and discusses the benefits of using ILs over more traditional approaches. Finally, the article demonstrates some technological challenges and how ILs could be used to further advance the production and specific property engineering of metal sulfide nanomaterials, again based on a number of selected examples.     

Novel Chiral Aminophosphine Ligand: Synthesis and Application in Asymmetric Catalytic Hydrogenation Reaction

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Synthesis and Characterization of Benzimidazolium Salts as Novel Ionic Liquids and their Catalytic Behavior in the Reaction of Alkylation

A new series of ionic liquids have been prepared containing benzimidazolium cation (abbreviated as Bim). These salts were characterized by DSC, NMR, elemental analysis and thermogravimetric analysis. They showed different properties compared to imidazolium cation due to the introduction of benzene ring. The alkylation of benzene/diphenyl ether with 1-dodecene was carded in C4eBimBr-AlCl3 ionic liquids showing high catalytic activity when the mole ratio of C4eBimB:AlCl3 was 1:2.     

Novel Chiral Aminophosphine Ligand:Synthesis and Application in Saymmetric Catalytic Hydrogenation Reaction

A new chiral aminophosphine ligand 6,6′-dimethoxy-2,2′-bis(diphenylphosphinoamino)biphenyl(DMBDPPABP) was prepared and its rhodium complex was found to be an effective catalyst for the asymmetric hydrogenation of amidoacrylic acid and its dervatives.The effects of solvent and reaction temperature on enantioselectivity were also studied.     

A Novel Green Synthesis of Quinolines through Acid-catalyzed Friedlander Reaction in Ionic Liquids

Quinoline derivatives were efficiently prepared through acid-catalyzed Friedlander reaction in ionic liquid ([bmim] [BF4]). It is shown that the proposed method is operationally simple and environmentally benign in that the reaction media and the catalyst can be recovered and be reused effectively for at least four times.     

Design, Synthesis of Chiral Ketone and Application in Asymmetric Epoxidation

A class of chiral ketone was synthesized for asymmetric epoxidation. High ee values have been obtained for a number of cis olefin and trans olefin. The epoxidation was stereospecific with no isomerizatiom observed in the epoxidation of acyclic system. Encourageingly high ee value has also been obtained for a number of terminal olefins. Mechanistic studies show that electronic interactions play an important role in the stereodifferentiation. O O O O O O NBoc O O t-BuO2CH2CN O O O …     

Preparation of Ionic Liquids and Their Application in Hydrogenation of Aromatic Nitriles

On the basis of their characteristic polar nature, phase behavior and lack of vapour pressure, ionic liquids are considered as green solvents and have attracted significant attention as an alternative reaction medium for homogeneous catalysis.[1] However, the "greenness" of typical ionic liquids used in the literature consisted of halogen-containing anions (such as [AlCl4]-, [BF4]- and [PF6]-) was limited in some sense, due to the serious environment concerns if the hydrolysis stability of the anion is poor (e.g. for [AlCl4]-and [PF6]-) or thermal stability of used ionic liquid is undesired. In both cases, the additional effort is needed to avoid the liberation of toxic and corrosive HF or HCl into the environment.     

Useful Application of Acidic Ionic Liquids as Solvents in Baeyer–Villiger Oxidation with Hydrogen Peroxide for the Synthesis of Lactones

Cyclic ketones have been efficiently oxidized with hydrogen peroxide using acidic ionic liquids (ILs) as solvents. This is a new method for the synthesis of lactones with high yields that does not utilize any additional catalysts and enables ILs to be recycled.     

Organic Reactions in Ionic Liquids： Ionic Liquid-promoted Efficient Synthesis of Disubstituted and Trisubstituted Thioureas Derivatives

In ionic liquid [Bmim][BF4], a series of disubstituted and trisubstituted thiourea derivatives were synthesized from phenyl and butyl isothiocyanate with a variety of amine in excellent yield.     

Ambient Ionic Liquids Used in the Reduction of Aldehydes and Ketones

The sodium borohydride reduction of aldehydes and ketones to corresponding alcohols has been accomplished via the use of ionic liquids. The alcohols are easily obtained with excellent yields and the ionic liquid BMImBF4 could be reused.     

Reactions of Binor-S with α,ω-Diols and Organic Acids in the Presence of Inorganic Ionic Liquids

Russian Journal of Organic Chemistry - New methods have been developed for the synthesis of previously unknown ω-(hexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetradecan-10-exo-yloxy)alkan-1-ols and...     

Cerium Alkoxides—Synthesis, Properties and Their Use in Michael Addition Reaction

Cerium(III) alkoxides served as an effective and attractive promoter for the Michael addition reaction with excellent chemical yields under mild conditions in short reaction time.     

Synthesis and Catalytic Application of Chiral 1, 1-Binaphthyl Polymers

Polymer-supported reagents and catalysts have attracted considerable attention as they offer alternative methods to separate and reuse expensive and often toxic chemicals1. Traditionally, the polymer-supported chiral catalysts are prepared by anchoring highly enantioselective monomeric catalysts to flexible and sterically irregular polymer supports. Because of the stereo-irregularity and flexibility of the traditional polymeric chiral catalysts, their catalytic sites do not have well-defined…     

Organic Reactions in Ionic Liquids： Ionic Liquid-promoted Three-component Condensation of Benzotriazole with Aldehyde and Alcohol

1-(α-Alkoxyalkyl)benzotriazoles are readily synthesized from three-component condensation of benzotriazole with aldehyde and alcohol in ionic liquid [Bmim]PF6.     

Synthesis of 2-Arylimidazo[1, 2-a]pyrimidines in Ionic Liquids

Room temperature ionic liquids were used as a “green“ recyclable alternative to conventional solvents in the synthesis of pharmaceutically useful compounds 2-arylimidazo[1, 2-a]pyrimidines through Tschotschibabin reaction of a-bromoacetophenones with 2-aminopyrimidine in good yields.     

Synthesis of 2-Acyl-2H-1,2,3-diazaphospholes and Their Diels-Alder Reaction with Cyclopentadiene

2H-1,2,3-Diazaphospholes 3a-3h were prepared from various ketone acylhydrazones and phosphorus trichloride in the presence of triethylamine. Compounds 3 underwent feasible hetero-Diels-Alder reactions with cyclopentadiene to afford the respective anellated [1,2,3]diazaphospholes 4a--4d as well as 4a‘--4d‘ in moderate yields. The endo rule in the reaction was observed under kinetic control conditions.     

Synthesis of Ketones with Alkyl Phosphonates and Nitriles as Acyl Cation Equivalent: Application of Dephosphonylation Reaction of β-Functionalized Phosphonate with Hydride

The preparation of several α-substituted ketones is performed in a one-pot procedure with alkyl phosphonates and aromatic nitriles by subsequent treatment of LiAlH₄. A new method for nitriles used as an acyl cation equivalent is described.     

π-Extended Pyrrole-Fused Heteropine: Synthesis,Properties, and Application in Organic Field-Effect Transistors

Sulfur-embedded polycyclic aromatic compounds have been used as building blocks for numerous organic semiconductors over the past few decades. While the success is based on thiophene-containing compounds, aromatic compounds that contain thiepine, a sulfur-containing seven-membered-ring arene, has been less well investigated. Here we report the synthesis and properties of π-extended pyrrole-fused heteropine compounds such as thiepine and oxepine. A π-extended pyrrole-fused thiepine exhibited a “pitched π-stacking” structure in the crystal, and exhibited a high charge carrier mobility of up to 1.0 cm² V⁻¹ s⁻¹ in single-crystal field-effect transistors.     

Synthesis and Catalytic Application of Chiral 1, l＇-Binaphthyl Polymers

The synthesis of a new type of polymers with main chain chirality based on BINOL skeleton is described. Titanium-BINOLate catalysts are easily generated from these polymers and applied to the asymmetric reaction of Et2Zn with benzaldehyde. The products are obtained in good yields with moderate enantioselectivities.