Deep eutectic solvent based on choline chloride and malonic acid as an efficient and reusable catalytic system for one-pot synthesis of functionalized pyrroles

Hu, Hai‐Chuan; Liu, Yuheng; Li, Baole; Cui, Zhen‐Shui; Zhang, Zhan‐Hui

doi:10.1039/c4ra13577f

Cited by 119 publications

(24 citation statements)

References 82 publications

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“…In contrast to conventional ILs, DES are biodegradable, safe, non‐toxic and inexpensiv. Choline based ionic liquids play a crucial role in organic synthesis . The advantages of present methods over previously reported methods includes‐i)employs reusable catalytic system; ii) metal and ligand free synthesis avoiding use of aprotic solvents; iii) fast reaction with excellent yields under mild conditions.…”

Section: Resultsmentioning

confidence: 98%

Deep Eutectic Solvent: An Efficient Catalyst for C-O Coupling Reactions.

Pant

Shankarling

2017

ChemistrySelect

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An efficient and facile route has been developed by using greener and reusable deep eutectic solvent (DES) for the synthesis of O-arylated ethers. This process involves nucleophilic aromatic substitution (S N Ar) of various strongly electrondeficient aryl/alkyl halides and phenols with different substituents resulting in good to excellent yields of products (80-96 %). A significant enhancement in the yield as well as rate of the reaction is observed with increase in presence of electron-withdrawing functionality attached to aryl halide moiety. Simplicity of this catalytic system, cheap cost and easy product isolation procedure makes this protocol economically viable and comparable to metal/ligand catalysed reactions utilizing aprotic solvents. Moreover, the other significant advantages of this method includes mild reaction conditions, short reaction times, easy work up procedure and recyclability of the catalyst up to four runs without remarkable loss in activity.

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Section: Resultsmentioning

confidence: 98%

Deep Eutectic Solvent: An Efficient Catalyst for C-O Coupling Reactions.

Pant

Shankarling

2017

ChemistrySelect

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“…For instance, Zhang et al used ChCl-MA as a catalyst and reaction medium to obtain substituted pyrroles via a one-pot four-component reaction of aldehydes, amines, 1,3-dicarbonyl compounds, and nitromethane. 85 García-Álvarez 86 presented a micro-review on the use of DESs as environmentally friendly reaction media in metal-catalyzed and metal-mediated organic reactions. The catalyst activity of bis(allyl)-ruthenium(IV) complexes in the isomerization of allylic alcohols was investigated in the presence of different DESs.…”

Section: Media For Reactionsmentioning

confidence: 99%

Deep eutectic solvents: designer fluids for chemical processes

Wazeer

Hayyan

Hadj-Kali

2017

J of Chemical Tech & Biotech

106

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The increasing demand for multi‐task green solvents has spurred the development of next‐generation liquid media such as deep eutectic solvents (DESs), which have recently attracted increased attention. DESs are mixtures of salts and complexing agents, having freezing points lower than those of starting individual components. Similarly to ionic liquids, DESs exhibit distinctive properties such as chemical and thermal stability, biodegradability, non‐flammability, and cost effectiveness. These features account for their wide range of applications, e.g. as extractants, reactants, catalysts, reaction media, additives, and lubricants. This review summarizes the recent research efforts directed at exploring the potential applications of DESs in various chemical processes. With the rapid publication of reports on this new generation of solvents, other roles also are expected to be seen sooner or later. © 2017 Society of Chemical Industry

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“…The term Deep Eutectic Solvent (DES) [1][2][3] is most commonly used to describe low melting liquids formed by combining organic salts such as choline chloride with urea or other hydrogen-bond donor components including carboxylic acids and alcohols. DES were initially popularised 4 as lower cost and more environmentally benign (greener) variants of non-volatile ionic liquids and have been used as non-aqueous electrolyte solutions, 5 and media for nanoparticle and materials synthesis, [6][7][8][9] solvents for catalysis 10 and as vehicles for delivery of active pharmaceutical ingredients 11,12 have been extensively investigated in recent years.…”

Section: Introductionmentioning

confidence: 99%

Hydrophobic Deep Eutectic Solvents Incorporating Trioctylphosphine Oxide: Advanced Liquid Extractants

Gilmore

McCourt

Connolly

et al. 2018

ACS Sustainable Chem. Eng.

101

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A low viscosity, hydrophobic eutectic solvent based on trioctylphosphine oxide (TOPO) has been developed and characterized, and its use as an extractant demonstrated for liquid−liquid separation of uranyl nitrate from aqueous acid. This strategy of liquefying the active extracting agent as a eutectic liquid produced liquids that contain an intrinsically high concentration of TOPO (ca. 80 wt %, 1.875 mol L −1 at χ TOPO = 0.50) and renders the use of an organic (hydrocarbon) diluent redundant.

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Deep eutectic solvent based on choline chloride and malonic acid as an efficient and reusable catalytic system for one-pot synthesis of functionalized pyrroles

Abstract: Deep eutectic solvent (DES) based on choline chloride and malonic acid was prepared and applied as dual catalyst and reaction medium for synthesis of functionalized pyrroles by one-pot, four-component reaction of amines, aldehydes, 1,3-dicarbonyl compounds and nitromethane.

Cited by 119 publications

References 82 publications

Deep Eutectic Solvent: An Efficient Catalyst for C-O Coupling Reactions.

Deep Eutectic Solvent: An Efficient Catalyst for C-O Coupling Reactions.

Deep eutectic solvents: designer fluids for chemical processes

Hydrophobic Deep Eutectic Solvents Incorporating Trioctylphosphine Oxide: Advanced Liquid Extractants

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