Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction

Noorpoor, Zeinab; Tavangar, Saeed

doi:10.1080/00958972.2021.1914333

Cited by 10 publications

(3 citation statements)

References 34 publications

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“…Also, when choline chloride is present alone, the desired reaction does not occur at all (table 2, entry 27). Subsequently, different amounts of the [ChCl][TEA] 2 solvent/catalyst system were tested (table 2, entries [28][29][30][31]. The effect of palladium as a catalyst was also investigated, revealing that no product was formed in its absence (table 2, entries 32-34), and the best efficiency was achieved with 0.006 g of the catalyst (table 2, entry 4).…”

Section: Optimization Of the Reaction Conditionsmentioning

confidence: 99%

Efficient base- and ligand-free palladium catalysed O -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent

Abbasi,

Sardarian

2024

R. Soc. Open Sci.

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In this paper, we present a novel and sustainable approach using choline chloride:triethanolamine as a green, efficient and reusable deep eutectic solvent (DES) for Pd-catalysed O -arylation reactions with Pd/BaSO 4 (10%). By using the unique properties of DESs, we successfully achieved C–O bond formation without the need for additional solvents, bases and ligands. This solvent/catalyst system ([ChCl][TEA] 2 ) functioned as a dual catalyst and solvent system, enabling fast and environmentally friendly C–O bond formation from phenol derivatives and electron-deficient aryl halides, leading to remarkable yields under mild reaction conditions. To identify and characterize this DES, we employed differential scanning calorimetry, thermogravimetric analysis, Fourier-transform infrared spectroscopy, refractive index, viscosity, the potential of hydrogen (pH) and conductivity measurements. One of the remarkable advantages of this DES system is its exceptional stability. This solvent/catalyst system exhibited high stability throughout the reaction cycles, showing no significant loss of activity. As a result, this DES and catalyst (Pd/BaSO 4 (10%)) can be easily recycled and re-used for up to three consecutive cycles, making it an economically and environmentally attractive option for organic reactions. Our approach offers several key benefits, including simple catalyst preparation, quick reaction times and excellent production efficiency.

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Section: Optimization Of the Reaction Conditionsmentioning

confidence: 99%

Efficient base- and ligand-free palladium catalysed O -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent

Abbasi,

Sardarian

2024

R. Soc. Open Sci.

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“…10 In terms of using noble metals as active sites for some reactions, copper is a suitable alternative to high-cost metals, such as gold, palladium, and platinum, because it is significantly more economical and has the ability to catalyze important transformations, including coupling reactions, Ullmann reactions, azide-alkyne cycloaddition, and gas phases. [11][12][13][14] It should be noted that copper catalysts are also used to produce aniline from nitrobenzene on an industrial scale. 15 To preserve the environment, eliminating pollution and conserving energy are imperative concerns in modern society.…”

Section: Introductionmentioning

confidence: 99%

Highly selective reduction of nitro compounds catalyzed by MOF‐derived glucose stabilized Fe₃O₄ under mild conditions

Bisafar,

Malmir,

Heravi

2023

J of Chemical Tech & Biotech

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BACKGROUNDToday, studies on the catalytic reduction of nitroarenes and dyes are of crucial because nitroarenes, especially 4‐nitrophenol (4‐NPh) and dyes, which are considered important pollutants in wastewater, can pose risks to humans. It is noteworthy that amines are known as valuable intermediates in many industries, therefore, providing an efficient method to achieve these compounds is necessary to protect the environment. In this project, a magnetic MOFs‐based catalyst (containing Cu species as an active site) was found to offer a unique and cost‐effective route for the catalytic reduction of nitroarene and organic dyes.RESULTSIn this study, a novel magnetic catalyst, Fe3O4@glu/Cu‐TAZ‐IMI, based on MOF was synthesized. The core‐shell structure of Fe3O4@glu, functionalized with aspartic acid with TAZ‐IMI and Cu(OAc)2, resulted in the formation of magnetic MOF structure. The structure of this new nanocomposite was identified by X‐ray diffraction (XRD), Fourier Transform Infrared Spectrometer (FTIR), Brunauer–Emmett–Teller (BET), Scanning electron microscopy/energy dispersive X‐ray (SEM/EDX), Thermogravimetric analysis (TGA), High‐resolution transmission electron microscopy (HRTEM), Value stream mapping (VSM), Raman spectroscopy and Inductively coupled plasma‐optical emission spectrometry (ICP‐OES). The catalytic performance of the synthesized catalyst was evaluated for the reduction of nitro compounds and organic dyes, and the results were validated by Gas chromatography‐mass (GC–MS) and ultraviolet light (UV–Vis) spectroscopy. Moreover, the rate constants for the reduction of 4‐NPh, Congo red (CR), and Methylene blue (MB) followed pseudo first‐order kinetics model, which calculated values of 0.31 min−1, 0.355 min−1 and 0.044 s−1, respectively.CONCLUSIONThe catalytic efficacy of Fe3O4@glu/Cu‐TAZ‐IMI catalyst remained intact during the reduction of nitroarenes and organic dyes in aqueous and mild conditions. The findings demonstrate that this novel heterogeneous mesoporous catalyst exhibits exceptional catalytic activity and remarkable stability towards reduction reactions. Moreover, owning to its thermal and structural stability, the catalyst could be easily magnetically separated, recovered, and reused for up to 10 consecutive cycles without experiencing significant activity decline, effectively preventing the depletion of copper species from its structure. © 2023 Society of Chemical Industry.

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“…Numerous procedures using various reagents have been described so far for the Ullmann synthesis of diaryl ethers. [25][26][27] In this sense, homogeneous copper-mediated methods have attracted interesting attention. [28][29][30] Heretofore, various reducing agents have been utilized as an electron source to activate the Cu species.…”

Section: Introductionmentioning

confidence: 99%

Fe₃O₄ supported [Cu(ii)(met)(pro-H)₂] complex as a novel nanomagnetic catalytic system for room temperature C–O coupling reactions

Ali,

Guda,

Oraibi

et al. 2023

RSC Adv.

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Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction

Cited by 10 publications

References 34 publications

Efficient base- and ligand-free palladium catalysed O -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent

Efficient base- and ligand-free palladium catalysed O -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent

Highly selective reduction of nitro compounds catalyzed by MOF‐derived glucose stabilized Fe₃O₄ under mild conditions

Fe₃O₄ supported [Cu(ii)(met)(pro-H)₂] complex as a novel nanomagnetic catalytic system for room temperature C–O coupling reactions

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Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction

Cited by 10 publications

References 34 publications

Efficient base- and ligand-free palladium catalysed O -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent

Efficient base- and ligand-free palladium catalysed O -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent

Highly selective reduction of nitro compounds catalyzed by MOF‐derived glucose stabilized Fe3O4 under mild conditions

Fe3O4 supported [Cu(ii)(met)(pro-H)2] complex as a novel nanomagnetic catalytic system for room temperature C–O coupling reactions

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Highly selective reduction of nitro compounds catalyzed by MOF‐derived glucose stabilized Fe₃O₄ under mild conditions

Fe₃O₄ supported [Cu(ii)(met)(pro-H)₂] complex as a novel nanomagnetic catalytic system for room temperature C–O coupling reactions