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Relevant academic research and scientific papers

A new water-soluble ligand for efficient copper-catalyzed Huisgen cycloaddition of aliphatic azides and alkynes

Efficient procedures for the copper-catalyzed Huisgen cycloaddition reaction in aqueous media were developed using a novel water-soluble catalytic ligand, 2-{4-[(dimethylamino)methyl]-1,2,3-triazol-1-yl}cyclohexan-1-ol (AMTC). A series of aliphatic and ar

Copper immobilized on biomimetic assembled calcium carbonate/carboxymethylcellulose hybrid: a highly active recoverable catalyst for CuAAC reactions

A novel copper immobilized on biomimetic assembled carboxymethylcellulose/calcium carbonate hybrid (CuII@CMC/CaCO3) as an efficient heterogeneous catalyst for the synthesis of 1,2,3-triazoles has been described herein. The fabrication of CuII@CMC/CaCO3 is accomplished through a bioinspired mineralization process using sodium carboxymethylcellulose (CMC-Na) as the template and ion exchange agent, while the metathesis, nucleation, assemble, hybridization, and immobilization of Cu(II) occurred by successful treatment with CaCl2, Na2CO3, and CuSO4 in water at room temperature. The resultant CuII@CMC/CaCO3 hybrid was well characterized by various analyses such as FT-IR, XRD, SEM, EDX, EDX-mapping, TEM, and TGA techniques. In the presence of low copper loading of CuII@CMC/CaCO3 hybrid, benzylic halides, azide, and alkynes proceeded smoothly to afford 1,4-disubstituted 1,2,3-triazoles in high yields. The catalyst can be conveniently recovered from the reaction mixture by filter and reused for at least 5 consecutive runs with a slight drop in its catalytic activity. The remarkable activity and stability of the catalyst may be attributed to the coordination of both carboxyl and hydroxyl groups of the hybrid of CMC/CaCO3.

Multicomponent click reactions catalysed by copper(I) oxide nanoparticles (Cu2ONPs) derived using Oryza sativa

Abstract: A procedure for the expedient synthesis of well-characterized Cu(I) oxide nanoparticles (Cu2ONPs) from Cu(II) salts by employing Rice (Oryza sativa) as a cheap and ready source of reducing as well as stabilizing agent has been demonstrated. The judicious choice of rice as a catalyst has helped in the symbiotic combination of two events: viz., acidic hydrolysis of starch to form glucose and the subsequent formal reduction of Cu2+ by the in-situ generated monosaccharide reducing sugar (glucose) under the alkaline condition to produce Cu2O. Further, rice was also found to be effectively stabilizing the nanoparticles from agglomeration. Optical and microscopic techniques were suitably employed for the characterization of the nanoparticles of approximately 10 nm size. Furthermore, the specifically generated nanoparticles were found to be active catalysts in an aqueous medium for Azide-alkyne Huisgen cycloaddition (Click reaction) under base free condition via one-pot multi-component addition for the synthesis of mono-, bis- and tris-1,2,3-triazoles in good to excellent yields. Graphic abstract: Cu2ONPs synthesized using hydrolysed Rice, an active catalyst for synthesis of mono-, bis- and tris-1,4-disubstituted 1,2,3-triazoles via one pot multicomponent reactions in water.[Figure not available: see fulltext.].

Dendrimer-encapsulated copper(II) immobilized on Fe3O4@SiO2 NPs: a robust recoverable catalyst for click synthesis of 1,2,3-triazole derivatives in water under mild conditions

Abstract: In this paper, we have introduced Fe3O4@SiO2-dendrimer-encapsulated Cu(II) as a heterogeneous reusable catalyst for Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction in good to excellent yields at ambient

Synthesis and antimycobacterial activity of disubstituted benzyltriazoles

The increasing prevalence of multidrug-resistant strains of Mycobacterium tuberculosis (Mtb), the pathogen of human tuberculosis (TB), serves as a strong incentive for the discovery and development of new agents for the treatment of this plight. In search

Synthesis of heterogeneous Ru(ii)-1,2,3-triazole catalyst supported over SBA-15: Application to the hydrogen transfer reaction and unusual highly selective 1,4-disubstituted triazole formation: Via multicomponent click reaction

In the present study, we demonstrate a simple and efficient method for ligand formation and covalent anchoring to a heterogeneous support via click reaction. The complex tris(triphenylphosphine)ruthenium(ii) dichloride [RuCl2(PPh3)3] anchored over the click modified ligand of SBA-15 forms a new highly efficient heterogeneous SBA-15-Tz-Ru(ii)TPP catalyst. Solid state 13C, 29Si, and 31P CP-MAS NMR spectra provide evidence for the formation of the heterogeneous catalyst. SBA-15-Tz-Ru(ii)TPP catalyst was screened for the multicomponent click cycloaddition reaction in water medium as a green solvent and it exhibited unusual and excellent selectivity for the formation of 1,4-disubstituted triazole product under mild reaction condition. In addition, SBA-15-Tz-Ru(ii)TPP catalyst also catalyzed the hydrogen transfer reaction of various carbonyl compounds with excellent catalytic activity to give the corresponding alcohols. The heterogeneous catalyst can be recycled and reused several times (five) without a loss in reactivity.

Cu(II)-Catalyzed Oxidative Formation of 5,5′-Bistriazoles

Copper(II) acetate under aerobic conditions catalyzes the formation of 5,5′-bis(1,2,3-triazole)s (5,5′-bistriazoles) from organic azides and terminal alkynes. This reaction is an oxidative extension of the widely used copper-catalyzed azide-alkyne “click”

DERIVATIVES OF 1,2,3-TRIAZOLYL CYCLOHEXAN-1-OL AND ITS USE

1,2,3-triazolyl cyclohexanol derivatives have been disclosed and their use as ligands accelerating the copper(I)-catalyzed azide-alkyne cycloaddition and the zinc(II)-catalyzed azide-nitrile cycloaddition.

Recoverable Cu/SiO2 composite-catalysed click synthesis of 1,2,3-triazoles in water media

An eco-friendly multicomponent reaction for the synthesis of 1,2,3-triazoles using a recoverable and recyclable Cu/SiO2 composite as the catalyst is reported. The reaction proceeds by mixing the benzyl halide, sodium azide, the alkyne and the catalyst in an aqueous medium to afford the desired products in excellent yields. The heterogeneous catalytic system showed high efficiency, performing the multicomponent Huisgen reaction in a green approach based on recoverability, recyclability and avoidance of waste. Microwave irradiation was also applied, substituting for conventional heating, resulting in excellent yields of the products with a dramatic reduction in the reaction time.

Copper salt of 12-tungstophosphoric acid: An efficient and reusable heteropoly acid for the click chemistry

Three components coupling of alkyl bromide, sodium azide and alkyne has been achieved using a catalytic amount of copper-exchanged phosphotungstic acid (Cu-TPA) in the presence of triethyl amine in DMF to afford substituted triazoles in good yields with h