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Relevant academic research and scientific papers

Electrochemical Synthesis of Benzo[ d]imidazole via Intramolecular C(sp3)-H Amination

An electrochemical dehydrogenative amination for the synthesis of benzimidazoles was developed. This electrosynthesis method could address the limitations of the C(sp3)-H intramolecular amination synthesis reaction and provide novel access to obtain 1,2-disubstituted benzimidazoles without transition metals and oxidants. Under undivided electrolytic conditions, various benzimidazole derivatives could be synthesized, exhibiting functional group tolerance.

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

The synthesis and structure of an amazing and stable carbonized material Cu-PC@OFM and its catalytic applications in water with mechanism explorations

An amazing and stable carbonized octahedral frame material Cu-PC@OFM was synthesized and characterized through HRTEM, SEM, XRD, XPS, and Raman spectroscopy and nitrogen adsorption/desorption analysis. In particular, the carbon matrix carrier loaded with nano-copper not only maintains the original structure, but also the nano copper particles generatedin situsignificantly improve the catalytic performance and stability. It was disclosed that the copper-based catalyst material Cu-PC@OFM showed high catalytic activity in the borrowing hydrogen reaction and the synthesis of 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives with high yields in water. This copper catalytic system provided a much greener and efficient catalyst for the synthesis of functionalized amines and 1-benzyl-2-aryl-1H-benzo[d]imidazoles with good recovery performance in water, which was the first example for the Cu-PC@OFM material-catalyzed synthesis of 1-benzyl-2-aryl-1H-benzo[d]imidazoles. In addition, a plausible reaction mechanism was proposed through some condition control experiments, deuterium labeling experiments and separation of intermediates experiments.

A pentanuclear Er (III) coordination cluster as a catalyst for selective synthesis of 1,2-disubstituted benzimidazoles

A new tridentate ligand (H3L) was prepared from the reaction of 6-formyl-2-(hydroxymethyl)-4-tert-butylphenol and 2-amino-4-nitrophenol. The ligand H3L and acetylacetone were treated with Er (NO3)3·5H2/sub

A Zirconium Indazole Carboxylate Coordination Polymer as an Efficient Catalyst for Dehydrogenation-Cyclization and Oxidative Coupling Reactions

Rational ligand design is crucial for achieving widespread applications of coordination polymers. The preparation, structural characterisation, and catalytic applications of zirconium (IV) coordination polymer (Zr-IDA), which was derived from 1-(carboxymethyl)-1H-indazole-5-carboxylic acid are reported. The Zr-IDA catalyst contains porous and highly crystalline particles with a quasi-spherical morphology around 100 nm in size, and Zr was coordinated with both O and N as shown by FT-IR and XPS measurements. Importantly, the Zr-IDA catalyst shows great activity, selectivity and stability in the oxidative coupling of benzyl cyanides with tert-butyl hydroperoxide to afford tert-butyl peresters, and the dehydrogenation cyclization of o-phenylenediamines with aromatic alcohols to afford 1,2-disubstituted benzimidazole derivatives. Mechanistic investigations were carried out to study these reactions and the developed catalytic system in more detail.

Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation

Natural dolomitic limestone (NDL) is employed as a heterogeneous green catalyst for the synthesis of medicinally valuable benzimidazoles, dihydropyrimidinones, and highly functionalized pyridines via C–N, C–C, and C–S bond formations in a mixture of ethan

BINAP-copper supported by hydrotalcite as an efficient catalyst for the borrowing hydrogen reaction and dehydrogenation cyclization under water or solvent-free conditions

A BINAP-Cu system supported by hydrotalcite has been developed and proved to be a highly efficient catalyst for the atom-efficient and green borrowing hydrogen reaction and dehydrogenative cyclization. This BINAP-Cu complex supported by hydrotalcite is highly air-stable and can be recycled at least five times under solvent-free conditions. Notably, 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives could be synthesized from alcohols in only one step with water as the solvent for the first time. This provided a much greener and efficient catalytic method towards the synthesis of functionalized amines, ketones and 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives with high yields under water or solvent-free conditions.

Tunable Triazole-Phosphine-Copper Catalysts for the Synthesis of 2-Aryl-1H-benzo[d]imidazoles from Benzyl Alcohols and Diamines by Acceptorless Dehydrogenation and Borrowing Hydrogen Reactions

Triazole-phosphine-copper complexes (TAP?Cu) have been synthesized and applied as tunable and efficient catalysts for the selective synthesis of fluoro-substituted 2-aryl-1H-benzo[d]imidazole and 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives from simple alcohols in only one step. TAP?Cu exhibited excellent and tunable catalytic activity for both dehydrogenation and borrowing hydrogen reactions with more than 80 examples being demonstrated for the first time. It was observed that the ligand played a critical role in catalyst activity. Mechanistic studies and deuterium labeling experiments indicated that the reactions proceeded by an initial and reversible alcohol dehydrogenation resulting in a copper hydride intermediate. This was also supported by the direct observation of a diagnostic copper hydride signal by solid-state infrared spectroscopy. The TAP?Cu-H complex showed absorptions at 912 cm?1 that could be assigned to copper?hydride stretches. Furthermore, the direct trapping of an intermediate bisimine was also successfully performed. (Figure presented.).

Nano Copper(0)-Stabilized on Alumina: Efficient and Recyclable Heterogeneous Catalyst for Chemoselective Synthesis of 1,2-Disubstituted Benzimidazoles and Quinoxalines in Aqueous Medium

Abstract: The present communication elicits the use of copper nanoparticles on aluminium oxide derived from Cu–Al hydrotalcite as a heterogeneous catalyst in the green and operationally simple approach for the synthesis of selective 1,2-disubstituted benzimidazoles and quinoxaline. Wide ranges of substituted o-phenylenediamines and aldehydes or α-bromo ketones were used to achieve the desired products using water as the reaction medium. The recoverability and reusability of the catalyst are the significant features in this eco-friendly green protocol. Graphical Abstract: A simple and efficient process for the synthesis of benzimidazoles and quinoxaline in presence of Cu(0)/Al2O3 catalyst at room temperature is described.

Simple and mild protocol for synthesis of 1,2- Disubstitued benzimidazoles using SBA-15-supported poly(4-styrenesulfonyl-(Perfluorobutylsulfonyl)Imide) catalyst

A simple method for the synthesis of several 1,2-disubstituted benzimidazoles catalyzed by strongly acidic SBA-15-supported poly(4-styrenesulfonyl-(perfluorobutylsulfonyl) imide) is described. The protocol furnished the products in moderate yield and good selectivity in the condensation of o-phenylenediamine with structurally diverse aldehydes under mild conditions. Taylor & Francis Group, LLC.