Brønsted Acidic Ionic Liquids as Efficient Catalysts for the Synthesis of Amidoalkyl Naphthols

A simple, clean, and environmentally benign three-component process for the synthesis of amidoalkyl naphthols using Brønsted acidic ionic liquids as efficient catalysts in solution and under solvent-free conditions is described.     

BrФnsted Acidic Ionic Liquids: Novel Efficient,Cost-effective and Reusable Solvent-catalysts for Ritter Reaction

Several Brnsted acidic ionic liquids(ILs) were synthesized and used as dual solvent-catalysts for the Ritter reaction of benzonitrile with tert-butanol. In particular, IL11([NSPTEA][OTF]) showed excellent catalytic activity for the Ritter reaction. In the presence of IL11, various nitriles and tertiary alcohols as well as secondary alcohols were converted smoothly to the corresponding amides in good to excellent yields. In addition, this cost-effective ionic liquid [NSPTEA][OTF] was easily separated from the reaction mixture by extraction with a small amount of water, and was recycled five times without any significant loss in activity.     

Brønsted Acidic Ionic Liquids as Efficient and Recyclable Catalysts for Protection of Carbonyls to Acetals and Ketals Under Mild Conditions

A series of acidic ionic liquids have been used as efficient catalysts for the protection of various carbonyl compounds at room temperature. The features of mild conditions, satisfactory isolated yield, simple workup, and the recyclability of the catalyst were present in this process.     

Brønsted Acidic Ionic Liquids: New,Efficient, and Green Promoter System for the Synthesis of 4(3H)-Quinazolinones

A simple, inexpensive, and efficient new synthesis of 4(3H)-quinazolinones from the reaction of 2-aminobenzamide with aroyl chlorides in the presence of two new halogen-free Brønsted acidic ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [(CH₂)₄SO₃HMIM][HSO₄] and 1-(4-sulfonic acid) butylpyridinium hydrogen sulfate [(CH₂)₄SO₃HPY][HSO₄], green and reusable catalysts, with excellent product yields under solvent-free conditions is reported. The products could be separated simply from the catalyst, and the catalyst could be recycled without noticeably decreasing the catalytic activity.     

Synthesis and Characterization of Dual Acidic Ionic Liquids

Novel ionic liquids with dual acidity, of which the cation contains Brφnsted acidity and anions contain Lewis acidity were synthesized. These ionic liquids obtained were identified by NMR, FF-IR, SDT and FAB-MS. Their acidities were determined by pyridine probe on IR spectrography.     

D,L‐α‐Tocopherol Synthesis Catalyzed by the Brønsted Acidic Ionic Liquids

Abstract

The synthesis of D,L‐α‐tocopherol from trimethylhydroquinone and isophytol using the Brønsted acidic SO₃H‐functionalized ionic liquids as catalysts was explored. The catalytic activities of the SO₃H‐functionalized ionic liquids were dependent on their anions. The yield of D,L‐α‐tocopherol also depended on the solvent, which was the reaction medium. A yield of 94.3% was obtained using the SO₃H‐functionalized ionic liquid with [BF₄ ^?] anion as catalyst in propylene carbonate/heptane. The reaction mixture exhibited good biphasic behaviors, so that the produced D,L‐α‐tocopherol could be separated by decantation. The SO₃H‐functionalized ionic liquids could be reused after the removal of water.     

One-pot Synthesis of Lewis Acidic Ionic Liquids for Friedel-Crafts Alkylation

Lewis acidic ionic liquids have been receiving extensive interest as green substitute for H2SO4, HF and AlCl3 catalysts in chemical processes1. In view of the principles of green chemistry2, ionic liquids themselves are highly expected to be obtained via …     

Solvent-Free Oxidation of Alcohols with Potassium Persulphate in the Presence of Brönsted Acidic Ionic Liquids

An efficient conversion of alcohols to aldehydes was achieved using potassium persulphate and 3-methylimidazolinium methane sulfonate.     

Mild and Efficient Chemoselective Tetrahydropyranylation of Alcohols Using Brønsted Acidic Ionic Liquid as Catalyst Under Solvent-Free Conditions

A straightforward and efficient method for preparation of morpholinium bisulfate ([mroH]HSO₄) as a novel acidic ionic liquid is reported. The application of this efficient and inexpensive acidic ionic liquid catalyst for tetrahydropyranylation of alcohols under mild and solvent-free conditions at room was investigated.     

BrØnsted Reusable Acidic Ionic Liquids Catalyzed Biginelli Reaction under Solvent-Free Conditions

Abstract

2-Pyrrolidonium hydrogensulfate, N-methyl-2-pyrrolidonium hydrogensulfate, and N-methyl-2-pyrrolidonium dihydrogenphosphate as Brønsted reusable acidic ionic liquids (ILs) catalyzed the preparation of 3,4-dihydropyrimidin-2(1H)-one (thione) derivatives from ethyl/methyl acetoacetate, urea/thiourea, and aromatic aldehydes under thermal solvent-free conditions.     

Brønsted Acidic Ionic Liquid as an Efficient and Reusable Catalyst for One-Pot,Three-Component Synthesis of Pyrimidinone Derivatives via Biginelli-Type Reaction Under Solvent-Free Conditions

A mild and efficient method has been developed for the preparation of pyrimidinone derivatives from the reaction of aromatic aldehydes with cyclopentanone and urea or thiourea in the presence of N-(4-sulfonic acid) butyl triethyl ammonium hydrogen sulfate ([TEBSA][HSO₄]) as the Brønsted acidic ionic liquid and effective catalyst under thermal and solvent-free conditions. Good yields, short reaction times, straightforward workup, reusability of the catalyst, and green conditions are the most obvious advantages of this procedure.

Catalysts Based on Immobilized Ionic Liquids with Brønsted Acid Sites in the Oxidation of Dibenzothiophene

Moscow University Chemistry Bulletin - Immobilized ionic liquids with Brønsted acidity containing fragments of nicotinic and phosphomolybdic acids are synthesized by two methods: suspension...     

Brønsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones

A novel ionic liquid, 3‐carboxymethyl‐1‐methylimidazolium bisulfate (CMImHSO₄), was synthesized and used as a recyclable catalyst for the Biginelli reaction under solvent‐free conditions. High yields of various substituted 3,4‐dihydropyrimidin‐2(1H)‐ones (or thiones) were obtained. The ionic liquid can be recovered and recycled easily without loss of activity.     

Synthesis and Characterization of Task‐Specific Ionic Liquids Possessing Two Brönsted Acid Sites

Abstract

Task‐specific ionic liquids possessing two Brönsted acid sites with –COOH, HSO^? ₄, or H₂PO^? ₄ groups have been designed, synthesized, and characterized. Under mild conditions and without any additional organic solvent, the esterification of isopropanol by chloroacetic acid could be carried out in these new task‐specific ionic liquids. In comparison with most of acidic ionic liquids in current use, these ionic liquids are halogen free and more environmentally benign as media and catalysts.     

Nitration of Simple Aromatics with NO2 under Air Atmosphere in the Presence of Novel Brønsted Acidic Ionic Liquids

Abstract

Aromatics nitrate with NO₂/air catalyzed by novel Brønsted acidic ionic liquids (ILs) without any volatile chlorinated organic solvent under mild conditions. The ILs employed were caprolactam based, [Caprolactam]X (X^?=pTSO^?, BSO^?, BF₄ ^?, NO₃ ^?), which are of relatively lower cost and lower toxicity than traditional imidazolium‐based ILs. The nitration reactions were carried out at ?15 to ?0°C first, then at room temperature for a longer time with a little excessive NO₂ (ca. 1.4 eqv.) for moderate yield (for toluene). The IL could be reused four times.     

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.     

Oxidation of Condensed Thiophene Derivatives with Brønsted Acidic Ionic Liquid

Moscow University Chemistry Bulletin - Abstract—A catalyst based on ionic liquid consisting of a pyridinium cation having Brønsted acidity and a molybdenum anion...     

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.     

Green,One-Pot,Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using a Brønsted Acidic Ionic Liquid as Novel and Reusable Catalyst

3-Methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [(CH₂)₄SO₃HMIM][HSO₄], a Brønsted acidic ionic liquid, has been used as an efficient, green, and reusable catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles using benzil, an aromatic aldehyde, and a primary amine in the presence of ammonium acetate under solvent-free conditions. The catalyst could be recycled and reused several times without noticeably decreasing the catalytic activity.