ChemInform Abstract: A Cu(I) Catalyzed Mild and General Synthesis of 1,4‐Disubstituted‐1,2,3‐triazoles from Terminal Acetylenes and in situ Generated Alkyl Azides.

López-Ruíz, Heraclio; Rojas‐Lima, Susana; Cerda-Pedro, José Emilio de la; Amador‐Sánchez, Yoarhy A.; Cortés-Hernández, Mayra; Perez‐Perez, Jovana

doi:10.1002/chin.201424144

Cited by 6 publications

(8 citation statements)

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“…The crude product was purified by column chromatography (CH 2 Cl 2 -MeOH 96 : 4 v/v) and its characterization is consistent with the literature. 14,24 Ligand exchange reactions. To a 20 mL round-bottom flask equipped with a magnetic stirrer were charged 0.5 mmol of the copper complex and stoiquiometric amounts of the respective triazole I or II.…”

Section: Synthesis Of Complexes 5-8mentioning

confidence: 99%

Copper(ii) complexes supported by click generated mixed NN, NO, and NS 1,2,3-triazole based ligands and their catalytic activity in azide–alkyne cycloaddition

et al. 2014

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The preparation and characterization of four new copper(ii) complexes supported by click generated mixed NN, NO, and NS 1,2,3-triazoles are reported. The four complexes display a 1 : 2 copper/ligand ratio and give monomeric units in the solid state. Crystal structures demonstrate that depending on the flexibility of the ligand NX (X = O, N, S) pendant arm, the coordination environment around the metal center can feature square planar or octahedral geometries. All four complexes are catalytically active at room temperature in a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction using sodium ascorbate as a reducing agent and water-ethanol as a solvent mixture. Complex 8 supported by the NS ligand displayed the best catalytic performance of the series allowing for the easy and high yielding preparation of a variety of mono-, bis- and tris-1,2,3-triazoles under low catalyst loadings.

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Section: Synthesis Of Complexes 5-8mentioning

confidence: 99%

Copper(ii) complexes supported by click generated mixed NN, NO, and NS 1,2,3-triazole based ligands and their catalytic activity in azide–alkyne cycloaddition

et al. 2014

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“…Besides some rare examples of special copper complexes, e.g. Cu(I)(tris(2‐dioctadecylaminoethyl)amine)Br that shows unusual solubility‐based thermomorphic properties in polar solvents that allows recovery of the active form by simple filtration, the most prevailing solution for effective catalyst recycling is the immobilisation of the active species on a solid support, such as charcoal, graphene oxide, alumina, clays or organic/inorganic hybrid materials . Among them, SiO 2 with grafted imidazolium cations was proved to be an excellent support, resulting in a stable catalyst that could be used several times under solvent‐free conditions.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous azide–alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material

Fehér

Nagy

Szabó

et al. 2018

Applied Organom Chemis

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Heterogeneous copper catalysts were prepared by the deposition of CuI on a hybrid material consisting of silica and a polymer with imidazolium moieties.The solid materials were characterised using solid-phase NMR, Fourier transform infrared, Raman and X-ray photoelectron spectroscopies and Brunauer-Emmett-Teller measurements. The formation of copper-carbene complexes was proved from Raman spectra and the results were supported by density functional theory calculations. The catalyst could be recycled efficiently with low loss of copper. Metal leaching was proved to be facilitated by the use of conditions typical for a homogeneous system (the presence of a polar solvent or the addition of a tertiary amine). Besides simple model reactions, the best catalyst was found to be suitable for the synthesis of triazoles of more elaborate structure, such as ferrocene or steroid derivatives.

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“…Heterocyclic compounds containing nitrogen or sulfur in their structure have attracted a great deal of attention, particularly in the pharmaceutical fields owing their abundance and their various biological properties . Among them, triazole, a class of heterocyclic compounds rich in nitrogen, has several applications such as, anti‐inflammatory,, anticonvulsant, antimicrobial,, anti‐cancer,, antiviral,, potent HIV integrase inhibitor,‐ antitubercular,,, antibacterial,,, herbicide, photosensitizers and fluorescent whitening ,. The interesting point for widespread uses of 1,2,3‐triazoles, particularly regarded in health applications, relies on their persistence, nontoxicity, higher solubility in aqueous media than other aromatic compounds, and sustainability in biological systems …”

Section: Introductionmentioning

confidence: 99%

“…The high price of nano‐copper powders, however, limits their application. Alongside of all these mentioned methods, researchers are still attempting to create new catalytic systems to replace copper ,,,,…”

Section: Introductionmentioning

confidence: 99%

Natural Polymer‐Based Copper/ Sandarac Resin Catalyzed Regioselective One‐Pot Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles under Ultrasonic Irradiation

2018

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A simple ultrasonic‐assisted method was developed for click synthesize of natural polymer based copper/sandarac resin (CuO/SD) by linking two different unit sandarac resin powder and Cu(CH3COO)2. The CuO/SD nanocomposite was characterized by Fourier‐transform infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), X‐ray photoelectron spectroscopy (XPS), energy‐dispersive X‐ray spectroscopy (EDX) and X‐ray diffraction (XRD). All these analysis, showed that the surface of sandarac resin was uniformly covered by a layer of CuO nanoplates. Subsequently, its catalytic activity was studied in the synthesis of 1,4‐disubstituted 1,2,3‐triazoles via a one‐pot three‐component reaction among benzyl halides, sodium azide and terminal alkynes in water under ultrasonic irradiation. The reduction of copper (II) complexes of terpene acids to catalytic species Cu (I) occurred under ultrasonic conditions during cavitation. The use of natural CuO/SD catalyst in combination with ultrasonic irradiation eliminated the need of a reducing agent, moreover, it is easily separable, and recyclable so made this already efficacious click reaction, even more user‐friendly.

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ChemInform Abstract: A Cu(I) Catalyzed Mild and General Synthesis of 1,4‐Disubstituted‐1,2,3‐triazoles from Terminal Acetylenes and in situ Generated Alkyl Azides.

Cited by 6 publications

References 1 publication

Copper(ii) complexes supported by click generated mixed NN, NO, and NS 1,2,3-triazole based ligands and their catalytic activity in azide–alkyne cycloaddition

Copper(ii) complexes supported by click generated mixed NN, NO, and NS 1,2,3-triazole based ligands and their catalytic activity in azide–alkyne cycloaddition

Heterogeneous azide–alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material

Natural Polymer‐Based Copper/ Sandarac Resin Catalyzed Regioselective One‐Pot Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles under Ultrasonic Irradiation

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