Copper(I)-doped Wyoming’s montmorillonite for the synthesis of disubstituted 1,2,3-triazoles

Jlalia, Ibtissem; Elamari, Hichem; Meganem, Faouzi; Herscovici, Jean; Girard, Christian

doi:10.1016/j.tetlet.2008.09.031

Cited by 55 publications

(24 citation statements)

References 37 publications

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“…So, immobilization of catalysts on suitable insoluble supports is one of the most reliable methods for improving the efficiency and recovery of catalysts and strongly recommended from the viewpoint of green chemistry . Zeolites, montmorillonite, polystyrene, chitosan and modified KIT‐5 are some of the notable supports that bring about the heterogeneous catalysis of regioselective, three‐component reactions of alkyl halides, sodium azide and terminal alkynes.…”

Section: Introductionmentioning

confidence: 99%

Copper(I) iodide supported on modified cellulose‐based nano‐magnetite composite as a biodegradable catalyst for the synthesis of 1,2,3‐triazoles

Sabaqian

Nemati

Heravi

et al. 2016

Applied Organom Chemis

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Nano‐Fe3O4@Cellulose‐NH2‐CuI as a novel magnetically separable composite was prepared and fully characterized using various techniques including Fourier transform infrared, X‐ray photoelectron and energy‐dispersive X‐ray spectroscopies, X‐ray diffraction, field‐emission scanning and transmission electron microscopies, thermogravimetric analysis and vibrating sample magnetometry. To obtain an appropriate structure and also to describe to some extent the different kinds of metal–ligand interactions present in the nano‐Fe3O4@Cellulose‐NH2‐CuI composite, covalent and electrostatic interactions, density functional theory model chemistry and quantum theory of atoms in molecules method were employed, respectively. This cellulose‐based heterogeneous catalyst can effectively promote the one‐pot three‐component reaction of a variety of terminal alkynes bearing substituted phenyls or propargylic alcohol together with substituted benzyl halides and sodium azide, so‐called click reaction, in water to afford the corresponding 1,4‐disubstituted 1,2,3‐triazoles with improved yields and regioselectivity. The magnetic catalyst was conventionally recovered using an external magnet and reused in at least four successive runs under the optimal reaction conditions, without appreciable loss of its activity.

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Section: Introductionmentioning

confidence: 99%

Copper(I) iodide supported on modified cellulose‐based nano‐magnetite composite as a biodegradable catalyst for the synthesis of 1,2,3‐triazoles

Sabaqian

Nemati

Heravi

et al. 2016

Applied Organom Chemis

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“…Synthesis and applications of copper nanoparticle catalysts is reviewed recently . Cu or Cu(I) nanoparticles supported on ionic polymer, zeolite, Wyoming's montmorillonite clay, silica, activated carbon and charcoal are reported to catalyze click reactions and hence it is very much imperative on our part to compare the CNOFs with these catalysts. In few of the above cases the catalyst preparation required harsh conditions such as heating at 500–600 ° C. Cu supported on ionic polymer and zeolite required azides for the reaction and reactions were carried out in DMF:water (4:1) or methanol‐water mixtures.…”

Section: Resultsmentioning

confidence: 99%

Highly Stable Copper Nanoparticles Linked to Organic Frameworks as Recyclable Catalyst for Three‐Component Click Cycloaddition in Water

Prakash

Gopidas

2016

ChemistrySelect

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Synthesis, characterization and catalytic applications of highly stable copper‐nanoparticles linked to aromatic frameworks are reported. Synthesis of these nanoparticles was achieved in a one‐pot reaction which involved the simultaneous reduction of CuCl2.2H2O and 4,4’‐biphenylene‐bis‐diazonium tetrafluoroborate using sodium borohydride. Copper atoms formed upon reduction of Cu ions undergo clustering, leading to the formation of copper nanoparticles. At the same time, 4,4’‐biphenylene‐bis‐diazonium tetrafluoroborate are converted to biphenylene biradicals, which undergoes rapid addition reactions with each other and also on to the nanoparticle surfaces resulting in the formation of aromatic framework linked Cu nanoparticles. Four different types of nanoparticles were prepared by varying the concentration of the metal salts and the ligands. The structure and morphology of these materials were studied using XRD, XPS, SEM and HRTEM analysis. The materials were found to be very good catalysts for click reactions between azides and alkynes and exhibited TOF values as high as 305400 h−1. They also efficiently catalyzed the one‐pot click reactions involving azide precursors, sodium azide and alkyne. TOF up to 99000 h−1 were observed for these reactions.

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“…10 However, most of the existing methods involve handling of unstable, toxic organic azides and using homogeneous catalysts which cannot be separated easily from the reaction media. For this purpose, immobilization of Cu(I) species on various supports such as alumina, 12 polymers, 13 Amberlyst, 14 zeolites, 15 activated charcoal, 16 titanium dioxide, 17 silica-supported N-heterocyclic carbene, 18 clay, 19 magnetic materials, 20 and aluminum oxyhydroxide nanofibers, 21 has received a remarkable attention in the Huisgen1,3-dipolar cycloaddition. Using heterogeneous catalysts is accompanied with several advantages such as fast and efficient recyclability of the catalyst, as well as facile separation of the products.…”

Section: Introductionmentioning

confidence: 99%

Direct access to stabilized Cu^I using cuttlebone as a natural-reducing support for efficient CuAAC click reactions in water

2016

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Cuttlebone@CuCl2 has efficiently catalyzed the one-pot azidonation of organic bromides, followed by regioselective azidealkyne 1,3-dipolar cycloaddition (CuAAC) reaction to produce the corresponding 1,4-disubstituted 1,2,3-triazole derivatives in excellent yields, in water. Importantly, cuttlebone not only used for successful immobilization of CuCl2 in order to its heterogenation, but also utilized as a natural-reducing platform which can reduce Cu II to the click-active stabilized Cu I . This mild three component synthetic approach avoids handling of hazardous and toxic azides, because of their in situ generation. Moreover, the catalyst has the advantages of being ligand-free, leaching-free, thermal stable, easy to synthesize from inexpensive commercially available precursors, environmentally friendly and recyclable for at least seven times without a significant decrease in its activity and selectivity.Scheme 1 Preparation of catalyst. Experimental MaterialsAll chemical reagents and solvents were purchased from Merck and Sigma-Aldrich chemical companies and were used as received without further purification. Cuttlebone was taken out from cuttlefish (Sepia esculenta), 25-28 which is commonly found in saltwater beaches like Persian Gulf in Iran. Instrumentation analysisThe purity determinations of the products and the progress of the reactions were accomplished by TLC on silica gel polygram STL G/UV 254 plates. The melting points of the products were determined with an Electrothermal Type 9100 melting point apparatus. The FT-IR spectra were recorded on pressed KBr pellets using an AVATAR 370 FT-IR spectrometer (Therma Nicolet spectrometer, USA) at room temperature in the range between 4000 and 400 cm -1 with a resolution of 4 cm -1 , and each spectrum was the average of 32 scans. NMR spectra were recorded on a NMR Bruker Avance spectrometer at 400 and 300 MHz in CDCl 3 as solvent in the presence of tetramethylsilane as the internal standard and the coupling constants (J values) are given in Hz. Elemental analyses were performed using a Thermo Finnigan Flash EA 1112 Series instrument (furnace: 900 ˚C, oven: 65 ˚C, flow carrier: 140 mL min -1 , flow reference: 100 mL min -1 ). Mass spectra were recorded with a CH7A Varianmat Bremem instrument at 70 eV electron impact ionization, in m/z (rel %). Elemental compositions were determined with an SC7620 Energy-dispersive X-ray analysis (EDX) presenting a 133 eV resolution at 20 kV. Surface analysis spectroscopy of the catalyst was performed in an ESCA/AES system. This system was equipped with a concentric hemispherical (CHA) electron energy analyzer (Specs model EA10 plus) suitable for X-ray photoelectron spectroscopy (XPS). Inductively coupled plasma (ICP) was carried out on a Varian, VISTA-PRO, CCD, Australia and 76004555 SPECTRO ARCOS ICP-OES analyzer. All yields refer to isolated products after purification by recrystallization.

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Copper(I)-doped Wyoming’s montmorillonite for the synthesis of disubstituted 1,2,3-triazoles

Cited by 55 publications

References 37 publications

Copper(I) iodide supported on modified cellulose‐based nano‐magnetite composite as a biodegradable catalyst for the synthesis of 1,2,3‐triazoles

Copper(I) iodide supported on modified cellulose‐based nano‐magnetite composite as a biodegradable catalyst for the synthesis of 1,2,3‐triazoles

Highly Stable Copper Nanoparticles Linked to Organic Frameworks as Recyclable Catalyst for Three‐Component Click Cycloaddition in Water

Direct access to stabilized Cu^I using cuttlebone as a natural-reducing support for efficient CuAAC click reactions in water

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Copper(I)-doped Wyoming’s montmorillonite for the synthesis of disubstituted 1,2,3-triazoles

Cited by 55 publications

References 37 publications

Copper(I) iodide supported on modified cellulose‐based nano‐magnetite composite as a biodegradable catalyst for the synthesis of 1,2,3‐triazoles

Copper(I) iodide supported on modified cellulose‐based nano‐magnetite composite as a biodegradable catalyst for the synthesis of 1,2,3‐triazoles

Highly Stable Copper Nanoparticles Linked to Organic Frameworks as Recyclable Catalyst for Three‐Component Click Cycloaddition in Water

Direct access to stabilized CuI using cuttlebone as a natural-reducing support for efficient CuAAC click reactions in water

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Direct access to stabilized Cu^I using cuttlebone as a natural-reducing support for efficient CuAAC click reactions in water