Ionic liquids based fluorination of organic compounds using electrochemical method

Khan, Zia Ul Haq; Kong, Dondan; Chen, Yongmei; Muhammad, Nawshad; Khan, Arif Ullah; Khan, Faheem Ullah; Tahir, Kamran; Ahmad, Aftab; Wang, Lei; Wan, Pingyu

doi:10.1016/j.jiec.2015.06.007

Cited by 24 publications

(11 citation statements)

References 67 publications

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“…Furthermore, for the PIL with the same anion, that is, [HSO 4 ], the refractive index value of the nitrile functionalized ionic liquid, [C 2 CNIM][HSO 4 ] is higher than the methyl functionalized PIL, [MIM][HSO 4 ]. , The high refractive index value of the nitrile functionalized ILs may be due to the additional electron mobility in the nitrile functionalized side chain compared to nonfunctionalized imidazolium alkyl chain. , Generally, the refractive indices increase with the increase of alkyl chain length of functional group attached to the cation as the mobility of the electrons was suggested to increase . Zahoor et al reported refractive index values for [MIM][HSO 4 ] which have differences with the current work are about 0.006. The fitting parameters and standard deviation of refractive indices for PILs are summarized in Table S2 in the SI.…”

Section: Resultsmentioning

confidence: 99%

“…Unlike common organic solvents, they have unique and superior physical properties such as very low vapor pressure, high thermal and chemical stabilities, nonflammability, distinctive solvation potential, low melting point, high ionic conductivities, and wide liquid temperature range making them distinct candidates for various applications . Owing to large possibility of combing the various cations and anions, ILs have received great attention in science and technology. − Recently, protic ILs have been the principle focus of numerous studies because of their simple synthesis methods, low cost of synthesis and purification, and their biodegradable nature. The most important property of protic ILs which differentiate them from other ILs is the easy transfer of a proton from the acid to base, to make proton donor and acceptor sites. , PILs have extensive applications and been applied in organic synthesis, chromatography techniques, electrolytes, catalyst, and solvent.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Structural Variations on the Thermophysical Properties of Protic Ionic Liquids: Insights from Experimental and Computational Studies

et al. 2017

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In this work, new protic ionic liquids (PILs) based on 1-methylimidazolium/1-propanenitrileimidazolium cations with hydrogen sulfate, methanesulfonate, trifluoromethanesulfonate, para-toluenesulfonate, trifluoroacetate, and acetate anions were synthesized. The structures and purity of the products were confirmed by using 1 H and 13 C NMR and CHNS elemental analysis. The effect of structural variations on the thermophysical properties, namely, refractive index, density, and viscosity, was evaluated in a wide temperature range. The viscosity and density values were measured within the temperature range of 293.15−373.15 K. The density values were used further to calculate more properties like thermal expansion coefficient, molecular volume, standard entropy, and the lattice energy. Moreover, the experimental values of viscosity were used for the calculation of activation energy. Refractive indices were measured within the temperature range of 293.15−323.15 K, and these values were also used in the calculation of electronic polarizability. Acid numbers of the prepared PILs were measured and correlated with their structure moiety. In addition, the density functional theory (DFT) calculations were performed to get a deeper insight into the effect of structural variations of the ion pairs on their physical properties.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of Structural Variations on the Thermophysical Properties of Protic Ionic Liquids: Insights from Experimental and Computational Studies

et al. 2017

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“…Because of their good conductivity, non-flammability, non-volatility and thermal stability, ionic liquids, such as Et 3 NÁnHF, have found widespread use as solvents in electrochemical fluorination reactions. [321][322][323][324][325][326] Recently, Fuchigami and coworkers demonstrated miscellaneous approaches to improve the electrochemical fluorination. One approach makes use of ultrasonication to promote the mass transport of the substrate due to the high viscosity associated with the ionic liquids.…”

Section: Anodic Halogenationmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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“…Besides these methods, electrochemical methods were also reported for the synthesis of dibenzazepine derivatives 23 – 26 . Electrochemical methods have a wide range of applications in the synthesis of electroactive compounds due to their excellent performance and no need for toxic chemical reagents or expensive noble metals 25 , 27 – 39 . Moreover, the discovery of new electrode materials, the development of multifunctional practical straightforward equipment, along with bio-renewable solvents will provide in the future robust, general and scale-up electrosynthetical processes compared to traditional methods 40 .…”

Section: Introductionmentioning

confidence: 99%

A green protocol for the electrochemical synthesis of a fluorescent dye with antibacterial activity from imipramine oxidation

Souri

Khoram

Nematollahi

et al. 2022

Sci Rep

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Electrochemical oxidation of imipramine (IMP) has been studied in aqueous solutions by cyclic voltammetry and controlled-potential coulometry techniques. Our voltammetric results show a complex behavior for oxidation of IMP at different pH values. In this study, we focused our attention on the electrochemical oxidation of IMP at a pH of about 5. Under these conditions, our results show that the oxidation of IMP leads to the formation of a unique dimer of IMP (DIMP). The structure of synthesized dimer is fully characterized by UV–visible, FTIR, 1H NMR, 13C NMR and mass spectrometry techniques. It seems that the first step in the oxidation of IMP is the cleavage of the alkyl group (formation of IMPH). After this, a domino oxidation-hydroxylation-dimerization-oxidation reaction, converts IMPH to (E)-10,10′,11,11′-tetrahydro-[2,2′-bidibenzo[b,f]azepinylidene]-1,1′(5H,5′H)-dione (DIMP). The synthesis of DIMP is performed in an aqueous solution under mild conditions, without the need for any catalyst or oxidant. Based on our electrochemical findings as well as the identification of the final product, a possible reaction mechanism for IMP oxidation has been proposed. Conjugated double bonds in the DIMP structure cause the compound to become colored with sufficient fluorescence activity (excitation wave-length 535 nm and emission wave-length 625 nm). Moreover, DIMP has been evaluated for in vitro antibacterial. The antibacterial tests indicated that DIMP showed good antibacterial performance against all examined gram-positive and gram-negative bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli and Shigella sonnei).

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Ionic liquids based fluorination of organic compounds using electrochemical method

Cited by 24 publications

References 67 publications

Effect of Structural Variations on the Thermophysical Properties of Protic Ionic Liquids: Insights from Experimental and Computational Studies

Effect of Structural Variations on the Thermophysical Properties of Protic Ionic Liquids: Insights from Experimental and Computational Studies

Electrochemical strategies for C–H functionalization and C–N bond formation

A green protocol for the electrochemical synthesis of a fluorescent dye with antibacterial activity from imipramine oxidation

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