Ytterbium (III) trifluoromethanesulfonate catalysed Friedel–Crafts acylation of 1-methylpyrrole in ionic liquid

Su, Weike; Wu, Chunlei; Su, Hao

doi:10.3184/0308234053431130

Cited by 14 publications

(8 citation statements)

References 23 publications

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“…Decantation of the products allowed the catalyst/IL mixture to be readily recycled. Using this approach, acylation of 1-methylpyrrole with acid anhydrides or acylchlorides has been reported using Yb(OTf) 3 in [C 4 pyr][BF 4 ] . Similar yields were found in the IL compared with CH 3 NO 2 or CH 2 Cl 2 , albeit with increased reaction rates.…”

Section: Acid−base-catalyzed Reactions In Ilsmentioning

confidence: 73%

Catalysis in Ionic Liquids

2007

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Pa ˆrvulescu and Hardacre Scheme 80. Thioacetalization and Transthioacetalization of Aromatic Aldehydes Scheme 81. Ethylenediammonium-Diacetate-Catalyzed Gewald Synthesis of 2-Aminothiophenes Scheme 82. Preparation of Bis-indolylmethanes through Electrophilic Substitution Reactions of Indoles with Aldehydes and Ketones in ILs Scheme 83. Conversion of Ethyl Cyclohexanone-2-carboxylate to Methyl Vinyl Ketone

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Section: Acid−base-catalyzed Reactions In Ilsmentioning

confidence: 73%

Catalysis in Ionic Liquids

2007

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“…Metal triflates, another class of Lewis acids, have been also reported for Friedel-Crafts acylation reactions in ILs. For example, acylation of 1-methylpyrrole with acid anhydrides or acyl chlorides has been reported using Yb(OTf) 3 in [C4pyr] [BF 4 ] (Su et al 2005). The reaction rate in the IL increased sharply, albeit the yields were found similar compared with CH 3 NO 2 or CH 2 Cl 2 .…”

Section: Friedel-crafts Reactionsmentioning

confidence: 93%

Ionic liquids and supercritical carbon dioxide: green and alternative reaction media for chemical processes

Liu

Zhang

et al. 2016

Reviews in Chemical Engineering

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Ionic liquids (ILs) and supercritical CO 2 (scCO 2 ) are two promising types of reaction media for green chemical processes due to their unique properties. They can be integrated into chemical reactions as catalysts and solvents to develop green and environment-friendly processes. This review presents current research trends aiming to solve the major chemical engineering issues in light of a fundamental understanding of these media. Applications of these media in the petrochemical industry, biochemical engineering, and fine chemical production are reviewed, suggesting the challenges and directions of utilizing them for green processes prospectively. These recent explorations and successful examples of applications demonstrate that ILs and scCO 2 offer huge potential for novel and green chemical engineering processes.

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“…Therefore, there has been a lot of focus on creating safe and effective ways to make pyrroles recently. Several synthetic protocols have been reported, including Friedel-Crafts acylation, [15] Crossed-Aldol/Claisen-Schmidt condensation, [16][17] and coupling reactions catalyzed by transition metals. [18][19][20] As is well known, the great fragrance volatility and low threshold of tiny molecular pyrrole compounds produced by the Maillard process or nonenzymatic browning reaction may limit their use as food flavorings.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Thermal Behavior of N‐Substituted Pyrrole Esters

Fan

Chu

et al. 2022

ChemistrySelect

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Using glucosamine hydrochloride as the starting material, 4‐(methoxycarbonyl)‐5‐methyl‐1‐propyl‐1H‐pyrrole‐2‐carboxylic acid (3) was initially created as an intermediate compound by cyclization and oxidation in order to create novel high temperature stable pyrrole compounds. Furthermore, Steglich esterification was used to produce N‐substituted pyrrole esters (4 a–4 t). All the new compounds were verified using nuclear magnetic resonance (1H and 13CNMR), infrared spectroscopy (IR), and high resolution mass spectrometry (HRMS). Thermogravimetry (TG), differential scanning calorimetry (DSC), and pyrolysis‐gas chromatography/mass spectrometry (Py‐GC/MS) techniques were used to examine the thermal behaviors of the compounds 4 f, 4 g, 4 i, and 4 q. Ester bonds from the pyrolysis products 4 g, 4 i, and 4 q might be severed which were consisted of the raw materials as well as the substrates, such as menthol, phenethyl and pyrrole derivatives which are commonly utilized in the sector of spices in foods and cigarette.

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Ytterbium (III) trifluoromethanesulfonate catalysed Friedel–Crafts acylation of 1-methylpyrrole in ionic liquid

Cited by 14 publications

References 23 publications

Catalysis in Ionic Liquids

Catalysis in Ionic Liquids

Ionic liquids and supercritical carbon dioxide: green and alternative reaction media for chemical processes

Synthesis, Characterization and Thermal Behavior of N‐Substituted Pyrrole Esters

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