- Mechanochemical click reaction as a tool for making carbohydrate-based triazole-linked self-assembling materials (CTSAMs)
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Various glycosides in which glycosylated triazole residues are anchored on to a central phenyl ring have been prepared under green reaction conditions by a solvent-free mechanochemical method. Some of the glycosides exhibited the ability to form gels when in contact with long chain hydrocarbons, e.g. hexane, heptane and octane, and this property was phase-selective. Thus, from a mixture of hexane-water, the compounds preferably absorbed the alkane to form a gel. The gelation ability was found to increase with an increasing number of substituents on the phenyl ring but only up to tetra-substitution. The hexa-substituted phenyl derivative did not swell in the hydrocarbon solvents investigated. The spontaneous self-assembling properties of these compounds in hexane have been investigated by transmission electron microscopy (TEM). Molecular modelling was used to optimize the structural geometry of these carbohydrate-based triazole-linked self-assembling materials (CTSAMs) and to rationalize their behaviour.
- Tyagi, Mohit,Taxak, Nikhil,Bharatam, Prasad V.,Nandanwar, Hemraj,Kartha, K.P. Ravindranathan
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Read Online
- Anti-Lung Cancer Activities of 1,2,3-Triazole Curcumin Derivatives via Regulation of the MAPK/NF-κB/STAT3 Signaling Pathways
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In this study, a series of curcumin derivatives containing 1,2,3-triazole were designed and synthesized, and their inhibitory activities against the proliferation of lung cancer cells were studied. Compound 5 k (3,4-dichlorobenzyltriazole methyl curcumin)
- Zhi, Tai Xin,Liu, Kai Qiang,Cai, Kun Yi,Zhao, Yu Chao,Li, Zhen Wang,Wang, Xin,He, Xin Hua,Sun, Xian Yu
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- Pyridinyl-triazole ligand systems for highly efficient CuI-catalyzed azide-alkyne cycloaddition
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Pyridinyl-triazole ligand systems (including N2-2-pyridinyl 1,2,3-triazoles and N1/N2-substituted 2-(NH-1,2,3-triazol-4-yl)pyridines) were found to be superior ligands for CuI-catalyzed azide-alkyne cycloaddition (CuAAC) r
- Chen, Yunfeng,Meng, Xianggao,Wang, Ye,Zheng, Lei
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- Copper(ii) complexes ofN-propargyl cyclam ligands reveal a range of coordination modes and colours, and unexpected reactivity
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The coordination chemistry ofN-functionalised cyclam ligands has a rich history, yet cyclam derivatives with pendant alkynes are largely unexplored. This is despite the significant potential and burgeoning application ofN-propargyl cyclams and related com
- Counsell, Andrew J.,Yu, Mingfeng,Shi, Mengying,Jones, Angus T.,Batten, James M.,Turner, Peter,Todd, Matthew H.,Rutledge, Peter J.
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supporting information
p. 3931 - 3942
(2021/03/29)
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- Tuning the optical properties of BODIPY dyes by N-rich heterocycle conjugation using a combined synthesis and computational approach
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The increased number of N-atoms induced a blueshift in absorption and a gain in fluorescence quantum yield, from 750 nm and ~0% for pyrrole to 635 nm and ~40% for triazole, respectively. DFT calculations indicated a decrease in HOMO energy levels with the
- Banala, Srinivas,Kiessling, Fabian,Merkes, Jean Michel,Ostlender, Tobias,Sun, Haitao,Wang, Fufang
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supporting information
p. 19641 - 19645
(2021/11/12)
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- Tris-isocyanide copper(I) complex enabling copper azide-alkyne cycloaddition in neat conditions
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The three-coordinated homoleptic Cu(I) complex with 2,6-dimethylphenyl isocyanide in the coordination sphere was easily synthesized and isolated as tetrafluoroborate salt. The structure of the compound was determined by single-crystal X-ray diffraction. T
- Ferraro, Valentina,Sole, Roberto,Bortoluzzi, Marco,Beghetto, Valentina,Castro, Jesús
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- Regioselective reduction of 1h-1,2,3-triazole diesters
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Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.
- Butler, Christopher R.,Bendesky, Justin,Schoffstall, Allen Milton
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- Immobilized galactose oxidase in alginate gel (GO-Bead): a versatile and efficient biocatalyst for the regioselective synthesis of 1,4-disubstitued-1,2,3-triazoles: click reaction
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Galactose oxidase (E.C. 1.1.3.9) is an extracellular oxidoreductase enzyme containing Cu(I) which is produced by some fungi like Fusarium species. The enzyme catalyzes the selective oxidation of primary alcohols like galactose. In this study, a heterogeneous enzymatic system for click reaction was prepared. The most important advantage of the heterogeneous catalyst is the ease of separation and their possible reusability. Therefore, galactose oxidase was immobilized by entrapment; for this purpose, alginate polysaccharide beads with different diameters were synthesized and galactose oxidase was immobilized into them to obtain galactose oxidase-bead (GO-Bead). Next, the catalytic activity of galactose oxidase-beads was examined in the one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles via click reaction comprising diversely benzyl halides, sodium azide and different alkynes in aqueous medium which need Cu(I) for their performance. The catalyst was conventionally recovered and effectively reused in several runs with no appreciable decrease in its catalytic activity.
- Akbari Gourdani, Fateme,Ghadam, Parinaz,Heravi, Majid M.,Malmir, Masoume
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p. 1471 - 1478
(2021/01/09)
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- Pyrazine Based Type-I Sensitizing Assemblies for Photoreduction of Cu(II) in ‘One-Pot Three-Component’ CuAAC Reaction Under Aerial Conditions
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Photosensitizing assemblies of pyrazine derivative PDA have been developed which exhibit a high photostability, ‘lighted’ excited state, balanced redox potential, high transportation potential and activate oxygen via type-I pathway only. These PDA assemblies in combination with Cu(II) ions catalyze the CuAAC reaction via in situ reduction of Cu(II) ions without any reducing or stabilizing agent. The present protocol has wide substrate scope with recyclability of the catalytic system up to six catalytic cycles and is applicable to gram-scale synthesis.
- Kumar, Sourav,Kumar, Manoj,Bhalla, Vandana
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supporting information
p. 3944 - 3950
(2021/10/19)
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- Catalytic performance of Cu(II)-supported graphene quantum dots modified NiFe2O4 as a proficient nano-catalyst in the synthesis of 1,2,3-triazoles
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Abstract: NiFe2O4 nanoparticles are modified by graphene quantum dots (GQDs) and utilized to stabilize the Cu(II) nanoparticles as a novel magnetically retrievable catalytic system (Cu(II)/GQDs/NiFe2O4) for gree
- Deilam, Razieh,Moeinpour, Farid,Mohseni-Shahri, Fatemeh S.
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- Dinuclear Cu(I) Halides with Terphenyl Phosphines: Synthesis, Photophysical Studies, and Catalytic Applications in CuAAC Reactions
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Several dinuclear terphenyl phosphine copper(I) halide complexes of composition [CuX(PR2Ar′)]2 (X = Cl, Br, I; R = hydrocarbyl, Ar′ = 2,6-diarylterphenyl radical), 1-5, have been isolated from the reaction of CuX with 1 equiv of the phosphine ligand. Most
- Beltrán, álvaro,Gata, Inmaculada,Maya, Celia,Avó, Jo?o,Lima, Jo?o Carlos,Laia, César A. T.,Peloso, Riccardo,Outis, Mani,Nicasio, M. Carmen
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supporting information
p. 10894 - 10906
(2020/08/12)
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- A bile acid-based pyridino-triazole ligand for Cu(I)-stabilization and its application in Cu(I) catalyzed click reactions
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A bile acid based pyridino-triazole ligand to stabilize Cu(I) state has been developed. The ligand was found to catalyze click reactions of a number of alkynes and azides in presence of Cu(CH3CN)4.BF4 at very low catalyst
- Nayal, Aradhana,Pandey, Pramod S.
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- Triazole-based, optically-pure metallosupramolecules; highly potent and selective anticancer compounds
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Functionalised triazole aldehydes are used in the highly selective self-assembly of water-compatible, optically pure, low symmetry Fe(ii)- and Zn(ii)-based metallohelices. Sub-micromolar antiproliferative activity is observed against various cancerous cel
- Brabec, Viktor,Clarkson, Guy J.,Coverdale, James P. C.,Kostrhunova, Hana,Phillips, Roger M.,Postings, Miles,Rogers, Nicola J.,Scott, Peter,Shepherd, Samantha L.,Song, Hualong
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supporting information
p. 6392 - 6395
(2020/06/21)
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- Tailor-Made Polydiacetylene Micelles for the Catalysis of 1,3-Dipolar Cycloadditions in Water
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A colloidal catalyst was developed by complexation of copper chloride in polydiacetylene micelles. The latter were designed to accommodate and stabilize copper salts, by providing a suitable ligand environment. Micelles were valorized as nanoreactors for
- Kumar, Ramar Arun,Jawale, Dhanaji V.,Oheix, Emmanuel,Geertsen, Valérie,Gravel, Edmond,Doris, Eric
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supporting information
p. 4425 - 4431
(2020/09/11)
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- A Class of FeIII Macrocyclic Complexes with Alcohol Donor Groups as Effective T1 MRI Contrast Agents
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Early studies suggested that FeIII complexes cannot compete with GdIII complexes as T1 MRI contrast agents. Now it is shown that one member of a class of high-spin macrocyclic FeIII complexes produces more intense contrast in mice kidneys and liver at 30 minutes post-injection than does a commercially used GdIII agent and also produces similar T1 relaxivity in serum phantoms at 4.7 T and 37 °C. Comparison of four different FeIII macrocyclic complexes elucidates the factors that contribute to relaxivity in vivo including solution speciation. Variable-temperature 17O NMR studies suggest that none of the complexes has a single, integral inner-sphere water that exchanges rapidly on the NMR timescale. MRI studies in mice show large in vivo differences of three of the FeIII complexes that correspond, in part, to their r1 relaxivity in phantoms. Changes in overall charge of the complex modulate contrast enhancement, especially of the kidneys.
- Abozeid, Samira M.,Asik, Didar,Bateman, Gage,Burgio, Ariel,Morrow, Janet R.,Snyder, Eric M.,Spernyak, Joseph A.,Turowski, Steven G.
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p. 2414 - 2419
(2020/01/02)
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- Synthesis and Characterization of Copper(I)‐Cysteine Complex Supported on Magnetic Layered Double Hydroxide as an Efficient and Recyclable Catalyst System for Click Chemistry Using Choline Azide as Reagent and Reaction Medium
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Abstract: In this study, Fe3O4@LDH@cysteine–Cu(I) nanoparticles as a novel and recyclable catalytic system was designed and successfully synthesized. These nanoparticles show high catalytic activity for preparation of the triazole fa
- Pazoki, Farzane,Salamatmanesh, Arefe,Bagheri, Sepideh,Heydari, Akbar
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p. 1186 - 1195
(2019/11/16)
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- Design, synthesis, and functional evaluation of a novel series of phosphonate-functionalized 1,2,3-triazoles as positive allosteric modulators of α7 nicotinic acetylcholine receptors
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The α7 nicotinic acetylcholine receptor is a pentameric ligand-gated ion channel widely distributed in the central nervous system, mainly in the hippocampus and cortex. The enhancement of its activity by positive allosteric modulators (PAMs) is a promising therapeutic strategy for cognitive deficits and neurodegenerative disorders. With the aim of developing novel scaffolds with PAM activity, we designed and synthesized a series of phosphonate-functionalized 1,4-disubstituted 1,2,3-triazoles using supported copper nanoparticles as the cycloaddition reaction catalyst and evaluated their activity on α7 receptors by single-channel and whole-cell recordings. We identified several triazole derivatives that displayed PAM activity, with the compound functionalized with the methyl phosphonate group being the most efficacious one. At the macroscopic level, α7 potentiation was evidenced as an increase of the maximal currents elicited by acetylcholine with minimal effects on desensitization, recapitulating the actions of type I PAMs. At the single-channel level, the active compounds did not affect channel amplitude but significantly increased the duration of channel openings and activation episodes. By using chimeric and mutant α7 receptors, we demonstrated that the new α7 PAMs share transmembrane structural determinants of potentiation with other chemically nonrelated PAMs. To gain further insight into the chemical basis of potentiation, we applied structure-activity relationship strategies involving modification of the chain length, inversion of substituent positions in the triazole ring, and changes in the aromatic nucleus. Our findings revealed that the phosphonate-functionalized 1,4-disubstituted 1,2,3-triazole is a novel pharmacophore for the development of therapeutic agents for neurological and neurodegenerative disorders associated with cholinergic dysfunction.
- Nielsen, Beatriz Elizabeth,Stabile, Santiago,Vitale, Cristian,Bouzat, Cecilia
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p. 2688 - 2704
(2020/10/13)
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- Synthesis, characterization and catalytic properties of a new binuclear copper(II) complex in the azide–alkyne cycloaddition
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A new binuclear copper(II)–oxalate complex containing 2,9-dimethyl-1,10-phenanthroline (dmp), was synthesized via a simple and one-pot reaction. [Cu2(dmp)2(ox)Cl2]·H2O (1) was characterized by single-crystal X-ray crystallography and IR methods. The complex 1 was been used to efficiently catalyze the three-component 1,3-Dipolar cycloaddition CuAAC reaction to produce 1,4-disubstituted 1,2,3‐triazoles in good to excellent yields from aromatic or aliphatic halide, sodium azide, and acetylene in water as a green solvent with low catalyst amount.
- Akbar Khandar, Ali,Amini, Mojtaba,Ellern, Arkady,Keith Woo, L.,Sheykhi, Ayda
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- Synthesis, Characterisation and Crystal structure of a New Cu(II)-carboxamide Complex and CuO nanoparticles as New Catalysts in the CuAAC reaction and Investigation of their Antibacterial activity
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The bidentate carboxamide ligand N-(thiazole-2-yl) picolinamide (LH) was synthesized in the environmentally friendly ionic liquid TBAB, and the five-coordinated CuII-complex, [Cu(L)2(H2O)].CHCl3 (1) was synthesized from LH and copper(II)acetate. Cupric oxide [CuO] nanoparticles (2) have been prepared by the thermal decomposition of (1) as a new precursor at 600 °C for 3 h under air atmosphere. (1) was characterised using FT-IR spectroscopy, elemental analyses and its solid state structure was confirmed by single crystal X-ray diffraction. (2) were identified by FT-IR spectroscopy, X-ray powder diffraction, scanning electron microscopy, energy dispersive X-ray analysis and thermo-gravimetric differential thermal analyses. The electrochemical behaviour of LH and (1) has been investigated by cyclic voltammetry: irreversible CuII/I reductions were observed. The catalytic activity of (1) and (2) were evaluated in the one-pot azide–alkyne cycloaddition click reaction in water without additional agents. LH, (1) and (2) were also screened for their in vitro antibacterial activity: they showed promising antibacterial activity comparable to that of the antibiotic penicillin.
- Kiani, Mahsa,Bagherzadeh, Mojtaba,Meghdadi, Soraia,Fadaei-Tirani, Farzaneh,Babaie, Maryam,Schenk-Jo?, Kurt
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- Azide–Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex
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A highly efficient and environmentally benign protocol for copper-catalyzed alkyne–azide cycloaddition (CuAAC) in industrially important alkane solvents was developed. New copper(I) complexes bearing NHC ligands decorated with bulky hexafluoroisopropylalk
- Topchiy, Maxim A.,Ageshina, Alexandra A.,Gribanov, Pavel S.,Masoud, Salekh M.,Akmalov, Timur R.,Nefedov, Sergey E.,Osipov, Sergey N.,Nechaev, Mikhail S.,Asachenko, Andrey F.
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supporting information
p. 1016 - 1020
(2018/12/11)
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- Cu nanoparticles immobilized on modified magnetic zeolite for the synthesis of 1,2,3-triazoles under ultrasonic conditions
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Magnetically recoverable copper nanoparticle-loaded natural zeolite (CuNPs/MZN) as an efficient catalyst was synthesized. The Fe3O4 magnetic nanoparticles were immobilized into the pores of natural clinoptilolite zeolite, which were
- Khakzad Siuki, Mohammad Mehdi,Bakavoli, Mehdi,Eshghi, Hossein
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- Synthesis of a novel resorcin[4]arene-glucose conjugate and its catalysis of the CuAAC reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water
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The Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) in aqueous media using resorcin[4]arene glycoconjugate (RG) is reported. The eight β-d-glucopyranoside moieties constructed on the resorcin[4]arene upper rim provide a pseudo-saccharide cavity that offers a suitable host environment for water-insoluble hydrophobic azido and/or alkyne substrates in water. The utility of RG was established as an efficient inverse phase transfer catalyst for the CuAAC in water as a green approach for the synthesis of 1,4-disubstituted 1,2,3-triazole species. The catalytic utility of RG (1 mol%) was demonstrated in a multicomponent one-pot CuAAC for various azido/alkyne substrates. The RG acts as a molecular host and a micro-reactor resulting in the 1,4-disubstituted 1,2,3-triazoles in excellent yield.
- Husain, Ali A.,Bisht, Kirpal S.
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p. 10109 - 10116
(2019/04/10)
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- Synthesis, characterization, and investigation of catalytic activity of copper(II) porphyrin graphene oxide for azide–alkyne cycloaddition
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Abstract: A covalently cross-linked graphene oxide (GO) catalyst was prepared by a cross-linking process using nucleophilic reaction of copper(II)‐coordinated 5,10,15,20-tetrakis(aminophenyl)porphyrin (CuPPh) with carboxyl groups at the edges of GO (GO–CuPPh). The structure of the catalyst was characterized using different techniques such as Fourier-transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive x-ray spectroscopy (EDS), thermogravimetric analysis (TGA), and inductively coupled plasma (ICP) spectroscopy. All analyses confirmed successful covalent immobilization of CuPPh on GO. The activity of the catalyst was then studied for synthesis of 1,4-disubstituted 1,2,3-triazoles derivatives by reaction of various aryl azides and different terminal alkynes in mild reaction condition with good to excellent yield. Graphical abstract: [Figure not available: see fulltext.].
- Khojastehnezhad, Amir,Bakavoli, Mehdi,Javid, Ali,Khakzad Siuki, Mohammad Mehdi,Shahidzadeh, Mansour
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p. 4473 - 4485
(2019/05/17)
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- CuI/L-proline catalyzed click reaction in glycerol for the synthesis of 1,2,3-triazoles
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Despite the apparent simplicity of the copper(I) iodide catalyzed CuAAC reaction, the conversion of the catalytic species, i.e. Cu(I) to thermodynamically more stable Cu(II), via aerial oxidation or disproportionation is a major issue. To stabilize the Cu
- Pasupuleti, Bala Gangadhar,Bez, Ghanashyam
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p. 142 - 146
(2018/12/11)
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- Ag-NHC anchored on silica: An efficient ultra-low loading catalyst for regioselective 1,2,3-triazole synthesis
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A silica-supported silver complex, Ag-NHC@SiO2, was prepared by an anchoring coordination technique, which was successfully employed for the click reaction under mild reaction conditions. The protocol offered the remarkable advantages of operat
- Garg, Anirban,Khupse, Nagesh,Bordoloi, Ankur,Sarma, Diganta
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supporting information
p. 19331 - 19337
(2019/12/24)
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- Preparation method for synthesizing 1,4-substituted 1,2,3-triazole from organic azide and terminal alkynes
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The invention belongs to the technical field of nitrogen-containing compound preparation, discloses a preparation method for synthesizing 1,4-substituted 1,2,3-triazole from organic azide and terminalalkynes, provides a method which is used for preparing
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Paragraph 0094; 0095
(2019/12/25)
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- Triazolyl RuII, RhIII OsII, and IrIII Complexes as Potential Anticancer Agents: Synthesis, Structure Elucidation, Cytotoxicity, and DNA Model Interaction Studies
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Novel conjugated ruthenium(II), rhodium(III), and iridium(III) organometallic complexes of triazoles 1 and 2 synthesized and evaluated for anticancer activity against cervical (HeLa), kidney (HEK293), nonsmall lung cancer (A549), and leukemia (MT4) cancer cell lines are reported herein. The complexes are κ2-N,C coordinated and have the formula [ML(Ar)Cl] (where L is 1-benzyl-4-phenyl-1H-1,2,3-triazole for 1 and 1-benzyl-4-hydroxymethyl-1H-1,2,3-triazole for 2, Ar is p-cymene for RuII and OsII and Cp? for RhIII and IrIII, and M is metal). NMR studies, including HMBC and NOESY, were employed to unambiguously elucidate their structures and provide their conformational information in solution. Single-crystal X-ray diffraction data have been used to establish the solid-state structures of selected complexes, which further confirm the structural elucidation by NMR. Dynamic NMR studies, such as differential transferred NOE, have been employed to distinguish between isomers 1a_I and 1a_II of ruthenium(II) complexes of triazole 1. The rhodium(III) (1b) and iridium(III) (1c) complexes exhibited good cytotoxic activities (CC50 = 4-6 μM) comparable to that of the drug auranofin against lung cancer A549 cell lines (CC50 = 4.69 μM). While triazole 1 based ruthenium(II) (1a) and osmium(II) (1d) complexes displayed modest anticancer activities against HeLa and HEK293 cell lines, the analogous rhodium(III) and iridium(III) complexes exhibited good potential (CC50 = 9-54 μM versus auranofin (3-9 μM)) against these cancer cell lines. Insightful NMR studies on the interaction between the DNA model guanosine 5′-GMP and the complexes 1b,c reveal a possible mode of action of the aquated complexes involving carbenylation with DNA bases or purines through the triazolyl proton H-5. From the findings, these complexes could possibly confer their cytotoxic activities through intercalation with the DNA of pathological cells. Therefore, carbenylation of the triazolylrhodium(III) and iridium(III) complexes by DNA guanosine 5′-GMP is proposed as a novel mode of DNA intercalation of these complexes in cancer cells.
- Rono, Charles K.,Chu, William K.,Darkwa, James,Meyer, Debra,Makhubela, Banothile C. E.
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p. 3197 - 3211
(2019/09/07)
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- An Efficient Mesoporous Cu-Organic Nanorod for Friedl?nder Synthesis of Quinoline and Click Reactions
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Within the green chemistry context, heterogeneous catalysis for the synthesis of N-heterocycles from renewable resources using non-precious metals has garnered great interest in terms of economic and environmental perspectives. Herein, we present a triazine functional hierarchical mesoporous organic polymer (HMOP) with nanorod morphology together with large BET surface area ~1218 m2 g?1, huge pore volumeγτ“;6 mL g?1 and dual micro/mesopore architectures. Subsequent Cu-coordination with nitrogen atoms of the HMOP provides a robust catalyst (Cu-HMOP) to accomplish multi-step cascade reactions for preparation of N-heterocycles by different routes. For instance, the Cu-HMOP efficiently catalyzes one-pot sequential multi-step oxidative dehydrogenative coupling of 2-aminobenzyl alcohol with diverse aromatic ketones to afford corresponding quinolines in excellent isolated yields (up to 97 %). Secondly, the present catalyst exhibits good aerobic oxidative dehydrogenation activity of amines to imines. Thirdly, for “click” reaction involving azides-alkynes, the Cu-HMOP produced quantitative yield for 1,4-disubstituted 1,2,3-triazole derivatives at room temperature using water as solvent. Verification of active metal leaching by a hot filtration test as well as reusability of the retrieved Cu-HMOP catalysts shows a consistent activity in the multi-component quinoline synthesis as model reaction.
- Elavarasan, Samaraj,Bhaumik, Asim,Sasidharan, Manickam
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p. 4340 - 4350
(2019/08/12)
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- 1. 2, 3 - Triazole alcohol derivatization ibuprofen and its preparation method (by machine translation)
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The invention of 1, 2, 3 - triazole alcohol derivatization ibuprofen and its preparation method belongs to the technical field of organic synthesis. The 1, 2, 3 - triazole alcohol derivatization ibuprofen, has the following structural formula: The prepar
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Paragraph 0020; 0021; 0023
(2019/04/11)
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- Oxidation of 1,4-disubstituted-1,2,3-triazoles with H2O2–CF3CO2H: efficient synthesis of 1,2,3-triazole 3-oxides
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A collection of 1,2,3-triazole-3-oxides was obtained from oxidation of the corresponding 1,4-disubstituted-1,2,3-triazoles mediated by a H2O2–CF3CO2H system through a simple protocol in good yields showing high
- González-Mojica, Norberto,Almazán-Sánchez, Leticia,García-Torres, Jesús G.,Santana-Martinez, Ivette,Martínez-Otero, Diego,Sánchez-Carmona, Miguel A.,Cuevas-Ya?ez, Erick
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supporting information
p. 679 - 687
(2019/02/16)
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- Synthesis and characterization of active cuprous oxide particles and their catalytic application in 1,2,3-triazole synthesis via alkyne-azide cycloaddition reaction in water
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Active cuprous oxide materials are synthesized from CuSO4.5H2O using sodium stannite as reducing agent in the presence of various stabilizers, viz., cetyl trimethyl ammonium bromide, sodium dodecyl sulphate, and polyvinyl pyrrolidone
- Sawkmie, Micky Lanster,Paul, Dipankar,Kalita, Gitumoni,Agarwala, Khushboo,Maji, Pradip K.,Chatterjee, Paresh Nath
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p. 3277 - 3288
(2019/11/11)
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- In situ preparation and characterization of novel CuI-functionalized poly[(methyl methacrylate)-co-maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3-triazoles via click reaction: Experimental and computational chemistry
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A CuI-functionalized poly[(methyl methacrylate)-co-maleimide] (CuI@[PMMA-co-MI]) nanocatalyst was prepared from in situ polymerization and functionalization of poly[(methyl methacrylate)-co-(maleic anhydride)] and well characterized using various techniques. From a computational viewpoint, we assessed two complexation models between copper nanoparticles and [PMMA-co-MI]. In this line, the metal–ligand interaction strength was also studied via density functional theory calculations and frontier molecular orbital analysis. Moreover, for presenting a quantitative description of the electronic features of immobilization of copper nanoparticles on polymeric support, the topological analysis of electron density and its Laplacian was performed through quantum theory of atoms in molecules. Finally, the catalytic activity of CuI@[PMMA-co-MI] as a heterogeneous nanocatalyst was successfully examined in the highly regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles via click reaction.
- Pourmohammad, Nargess,Heravi, Majid M.,Ahmadi, Shervin,Hosseinnejad, Tayebe
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- Method used for synthesizing 1, 4-substituted 1, 2, 3-triazole from terminal alkyne multiple components
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The invention belongs to the technical field of nitrogen containing compound preparation, and discloses a method used for synthesizing 1, 4-substituted 1, 2, 3-triazole from terminal alkyne multiple components. The method comprises following steps: 1.2 eq
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Paragraph 0090; 0091
(2019/12/08)
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- Copper aluminate spinel in click chemistry: An efficient heterogeneous nanocatalyst for the highly regioselective synthesis of triazoles in water
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An expeditious protocol for the one-pot synthesis of 1,4-disubstituted (β-hydroxy)-1,2,3-Triazoles in an aqueous medium has been developed using copper aluminate nanoparticles. This heterogeneous catalytic system was found to drive a multicomponent click reaction between organic azides (generated in situ from epoxides or halides) and terminal aliphatic or aromatic alkynes in up to 96percent yield without the need for a reducing agent. Structurally diverse 1,2,3-Triazoles were synthesized in good to excellent yields, and the catalyst could be easily separated by simple filtration, recycled, and reused in six subsequent cycles.
- Kavoosi, Leila,Khalafi-Nezhad, Ali,Khalili, Dariush
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supporting information
p. 2136 - 2142
(2019/11/25)
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- Free-radical-mediated copper-catalyzed triazole formation under UV-irradiation
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Methoxy-polyethylene glycol (MPEG)-doped Cu (I)-polyaniline acts as an efficient catalyst for the 1,2,3-triazole formation reaction. The catalyst shows excellent performance when the reaction was carried out under ultraviolet irradiation conditions due to
- Nandi, Debkumar,Taher, Abu,Isalm, Rafique Ul,Mallick, Kaushik
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- Preparation and investigation of copper–manganese mixed oxides as a high-efficiency catalyst for the azide-alkyne 1,3-dipolar cycloaddition reaction
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The present work is developed for the catalysis of azide-alkyne 1,3-dipolar cycloaddition reaction with the aid of copper–manganese mixed oxides nanoparticles. The Cu/MnOx nanoparticles have been synthesized by a coprecipitation procedure. Characterizatio
- Amini, Mojtaba,Salmani, Somaiyeh,Gautam, Sanjeev,Chae, Keun Hwa
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- Silver and copper nanoparticles stabilized on ionic liquids-functionalized polyhedral oligomeric silsesquioxane (POSS): Highly active and recyclable hybrid catalysts
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Two novel heterogeneous hybrid catalysts were successfully synthesized using octa-aminopropyl polyhedral oligomeric silsesquioxane hydrochloride salt (OA-POSS) and ionic liquids, followed by immobilization of Cu and Ag nanoparticles. The obtained hybrid catalysts, Cu@POSS-ILs and Ag@POSS-ILs, were characterized using FT-IR, SEM, EDX, TEM, XRD and TGA. Catalytic studies demonstrated that Cu@POSS-ILs was an excellent catalyst for click reaction in aqueous medium. Furthermore, Ag@POSS-ILs was also exhibited to be an active catalyst for 4-nitrophenol (4-NP) reduction. Simple preparation and easy catalysts recovery and recyclability of Cu@POSS-ILs and Ag@POSS-ILs for at least 3 and 6 runs, respectively, without loss of catalytic activity could be considered as important advantageous from catalytic application point of view.
- Akbari, Ali,Naderahmadian,Eftekhari-Sis, Bagher
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p. 228 - 236
(2019/08/07)
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- Synthesis, characterization, and comparison of two new copper(II)complexes containing Schiff-base and diazo ligands as new catalysts in CuAAC reaction
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Two copper(II)complexes were synthesized through the reaction of Cu(OAc)2·H2O with a Schiff-base ligand (1-(((3,4-dichlorophenyl)imino)methyl)naphthalen-2-ol)and a diazo ligand (1-((3,4-dichlorophenyl)diazenyl)naphthalen-2-ol)in methanol. The complexes and ligands were characterized employing elemental analysis and electronic spectra. In addition, the ligands were fully characterized by using several 1D and 2D NMR techniques. Single crystal X-ray crystallography was also used for the characterization of some of these materials. Due to finding out the effect of Schiff-base and diazo ligands nature on the catalytic activity, the complexes were catalytically compared in one-pot azide-alkyne cycloaddition reaction in water. Furthermore, computational studies were performed on ligands and complexes for further understanding of the relationship between structure, bonding, and reactivity of these new materials.
- Bagherzadeh, Mojtaba,Mahmoudi, Hamed,Ataie, Saeed,Hafezi-Kahnamouei, Mohammad,Shahrokhian, Saeed,Bellachioma, Gianfranco,Vaccaro, Luigi
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supporting information
p. 213 - 220
(2019/05/01)
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- Copper(II) Nitrate Catalyzed Azide–Alkyne Cycloaddition Reaction: Study the Effect of Counter Ion, Role of Ligands and Catalyst Structure
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Abstract: For the first time, CuAAC reaction catalyzed by copper(II) nitrate and counter ion effect of various copper(II) salts are reported. Use of a novel copper complex 1, derived from the reaction of copper(II) nitrate with 5-acetyl-2-amino-6-methyl-4
- Bihani, Manisha,Pasupuleti, Bala G.,Bora, Pranjal P.,Bez, Ghanashyam,Lal, Ram A.
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p. 1315 - 1323
(2018/05/03)
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- Photoredox Catalysis at Copper(II) on Chitosan: Application to Photolatent CuAAC
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In this article we report the first example of a heterogeneous photolatent catalyst for the copper-catalyzed azide-alkyne cycloaddition (CuAAC) that is supported on chitosan. The heterogeneous copper(II) precatalyst was easily prepared by reaction of [Cu
- Jennah, Oumayma,Beniazza, Redouane,Lozach, Cédric,Jardel, Damien,Molton, Florian,Duboc, Carole,Buffeteau, Thierry,El Kadib, Abdelkrim,Lastécouères, Dominique,Lahcini, Mohammed,Vincent, Jean-Marc
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p. 4615 - 4624
(2018/10/26)
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- A recyclable/reusable hydrotalcite supported copper nano catalyst for 1,4-disubstituted-1,2,3-triazole synthesis via click chemistry approach
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Using hydrotalcite as solid support, copper nano particles were synthesized and used in azide-alkyne cycloaddition reaction en route to the synthesis of 1,4-disubstituted-1,2,3-triazoles. The catalyst is heterogeneous and can be recycled and reused easily
- Chetia, Mitali,Singh Gehlot, Praveen,Kumar, Arvind,Sarma, Diganta
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supporting information
p. 397 - 401
(2018/01/01)
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- CTAB promoted CuI catalyzed green and economical synthesis of 1,4-disubstituted-1,2,3-triazoles
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A practical, straightforward, and highly efficient CuI mediated green protocol for the regioselective synthesis of 1,4-disubstituted-1,2,3-triazole was developed using cetyltrimethylammonium bromide as a cheap additive in good to excellent yields. Low cat
- Ali, Abdul Aziz,Sharma, Rahul,Saikia, Prakash J.,Sarma, Diganta
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supporting information
p. 1206 - 1212
(2018/04/02)
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- Synthesis, spectroscopic characterization, and DFT studies of 1,2,3-triazole-based organosilicon compounds
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A series of triorgnosilicon compounds containing 1,2,3-triazole cores, tris(trimethylsilyl)ethyl) 1,2,3-triazoles (TTMSTs), tris(dimethyl(phenyl)silyl)ethyl) 1,2,3-triazoles (TDMPSTs), and bis(trimethylsilyl)vinyl) 1,2,3-triazoles (BTMSVTs) was synthesized and characterized by elemental analysis, FT-IR, 1H, 13C NMR spectroscopy, and density functional theory (DFT). The structure of the synthesized compounds was optimized using the B3LYP method of DFT at 6–311++G(d) basis set. Conjugate interactions or charge transfer in molecular systems was investigated using natural bond orbital (NBO) analysis. In addition, the FMOs (frontier molecular orbitals) and the associated band gaps were calculated and depicted. The mapped molecular electrostatic potential (MEP) surfaces of the title compounds were also calculated with the same level of theory.
- Mousazadeh, Hanieh,Safa, Kazem D.,Ghadari
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p. 200 - 208
(2018/06/19)
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- NHC-copper complexes immobilized on magnetic nanoparticles: Synthesis and catalytic activity in the CuAAC reactions
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A series of N-heterocyclic carbene copper(I) and rare copper(II) complexes (NHCCuCl or NHCCuCl2) were covalently immobilized directly on the surface of magnetic nanoparticles (MNPs) for the first time. The physicochemical properties were investigated by a broad range of techniques, including SEM and TEM microscopy, and TG analysis. The supported complexes exhibited excellent activity in the Huisgen cycloaddition with in situ generated azides. Unexpectedly, a direct comparison of NHCCuCl and NHCCuCl2 complexes anchored to the magnetic nanoparticles confirmed the higher activity of the latter for the formation of 1,2,3-triazoles, also under ascorbate-free conditions.
- Misztalewska-Turkowicz,Markiewicz,Michalak,Wilczewska
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- A one-pot method for synthesis of reduced graphene oxide-supported Cu–Cu2O and catalytic application in tandem reaction of halides and sodium azide with terminal alkynes
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Reduced graphene oxide (RGO)-supported Cu–Cu2O nanocomposite material (Cu-Cu2O@RGO) was prepared through a one-pot reflux synthesis method. The morphology, crystal structure and composition of the prepared Cu-Cu2O@RGO were characterized using transmission electron microscopy, X-ray diffraction, and X-ray photoelectron, infrared and Raman spectroscopies. Cu-Cu2O@RGO as a heterogeneous catalyst was applied to tandem reactions of halides and sodium azide with terminal alkynes to synthesize effectively 1,4-disubstituted 1,2,3-triazoles. Moreover, the catalyst showed excellent recyclability performance with very little leaching of the metal. Compared with homogeneous catalysts, Cu-Cu2O@RGO as a green and efficient catalyst was recoverable, easy to separate and highly stable in the tandem method for the synthesis of 1,2,3-triazole compounds.
- Li, Zhuofei,Zhao, Hongyan,Han, Huatao,Song, Jinyi,Liu, Yang,Guo, Weihao,Sun, Zhizhong,Chu, Wenyi
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- Copper(I)–Caffeine Complex Immobilized on Silica-Coated Magnetite Nanoparticles: A Recyclable and Eco-friendly Catalyst for Click Chemistry from Organic Halides and Epoxides
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Abstract: Copper(I)–caffeine complex immobilized on silica-coated magnetite nanoparticles was successfully synthesized and fully characterized by analyzing FT-IR, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray, inductively couple
- Salamatmanesh, Arefe,Kazemi Miraki, Maryam,Yazdani, Elahe,Heydari, Akbar
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p. 3257 - 3268
(2018/09/06)
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- CuI-functionalized halloysite nanoclay as an efficient heterogeneous catalyst for promoting click reactions: Combination of experimental and computational chemistry
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Amine-functionalized halloysite nanotubes (HNTs-2?N) were prepared and further modified by introduction of salicylaldehyde and formation of imine functionality (HNTs-2?N-Sal). The latter was subsequently used for immobilization of CuI and formation of CuI@HNTs-2?N-Sal, which could effectively promote click reactions of terminal alkynes, sodium azide and α-haloketones or alkyl halides in aqueous media and under mild reaction conditions to afford 1,2,3-triazoles in relatively short reaction times. Notably, the catalyst could be recycled in up to six reaction runs with negligible loss of catalytic activity and CuI leaching. Also, the geometry of CuI adsorption on the modified HNTs surface was explored by molecular simulation with density functional theory. Furthermore, topographic steric maps of possible coordination modes were obtained using the recently released SambVca2 web application tool. Based on obtained results, a catalytic site with superior performance was suggested.
- Bahri-Laleh, Naeimeh,Sadjadi, Samaheh,Heravi, Majid M.,Malmir, Masoumeh
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- Simple preparation of cuprous oxide nanoparticles for catalysis of azide–alkyne cycloaddition
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Cuprous oxide (Cu2O) nanoparticles were prepared by two simple methods and their structural, morphological and electronic properties were investigated by X-ray diffraction analysis, X-ray absorption near-edge structure, energy dispersive X-ray analysis and scanning electron microscopy. Cuprous oxide nanoparticles efficiently catalyse 1,3-dipolar cycloaddition of a variety terminal alkynes and organic azides producing the corresponding 1,2,3-triazole derivatives in excellent yields without use of any additives. Phenylacetylene and benzyl chloride were chosen as model starting compounds for the optimisation of the reaction conditions, such as effect of solvent, reaction temperature and time of reaction in the presence of a-Cu2O nanoparticles as a catalyst. The results showed that using cuprous oxide nanoparticles (0.035 mmol) and heating at 70 °C in water, the reaction of phenylacetylene with benzyl chloride and sodium azide gave 1-benzyl-4-phenyl-1H-1,2,3-triazole almost quantitatively in 6 h of reaction time. A study of the recyclability and reusability of the catalyst revealed that a-Cu2O could be reused at least five times without significant loss of yield.
- Amini, Mojtaba,Ramezani, Sakine,Anbari, Alireza Pourvahabi,Beheshti, Abolghasem,Gautam, Sanjeev,Chae, Keun Hwa
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p. 166 - 169
(2018/04/20)
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- Carbon nanotube-copper ferrite-catalyzed aqueous 1,3-dipolar cycloaddition of: In situ -generated organic azides with alkynes
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A novel nanohybrid catalyst was developed by assembling copper ferrite nanoparticles on carbon nanotubes. The supramolecular catalyst was applied to the one-pot azidation/1,3-dipolar cycloaddition of various substrates, at room temperature, and in an aqueous medium. The nanohybrid could also be recycled and reused by means of magnetic recovery.
- Prakash, Praveen,Kumar, Ramar Arun,Miserque, Frédéric,Geertsen, Valérie,Gravel, Edmond,Doris, Eric
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supporting information
p. 3644 - 3647
(2018/04/12)
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- Copper (I) complex of 2,9-dimethyl-1,10-phenanthroline: Synthesis, structure, and catalytic properties
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A copper (I) complex containing 2,9-dimethyl-1,10-phenanthroline (dmph), [Cu(dmph)2]Cl·6H2O, was prepared by reaction of CuCl2·2H2O and 2,9-dimethyl-1,10-phenanthroline in an aqueous solution at pH = 11 and characterized using elemental analysis, IR, EDX and X-ray crystallography. The complex consists of a mononuclear copper (I) surrounded by four coordinating nitrogen atoms of two dmph ligands, one Cl? anion and six H2O molecules. This novel cupper (I) complex was used as a catalyst for alkyne-azide cycloaddition (CuAAC) reaction to produce several 1,2,3-triazoles in high yields. The presented catalytic system fulfils the requirements of “click chemistry” with its soft and appropriate conditions, notably in water as solvent with low catalyst amount without any co-catalyst or activator.
- Amini, Mojtaba,Najafi, Shabnam,Janczak, Jan
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p. 333 - 339
(2018/06/29)
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