- Microwave-assisted facile synthesis of propargylamine library by robust nitro functionalized cross-linked polystyrene resin supported Cu NPs
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In the present investigation, we study catalytic activity of copper nanoparticles stabilized onto a nitro functionalized polystyrene resin (Cu NPs@ Nitro-Resin). The size of stabilized copper nanoparticles was found between 3 and 9?nm. This work reports a
- Sharma, Anuj S.,Kaur, Harjinder,Barot, Nirav
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- Gold nanoparticles immobilized on lipoic acid functionalized SBA-15: Synthesis, characterization and catalytic applications
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Gold nanoparticles immobilized on lipoic acid functionalized SBA-15 (SBA-LAG) catalyst was synthesized via functionalization of SBA-15 with propylamine followed by tethering of lipoic acid and immobilization of gold nanoparticles. The structural and texct
- Anand, Narani,Ramudu, Pochamoni,Reddy, Kannapu Hari Prasad,Rao, Kamaraju Seetha Rama,Jagadeesh, Bharatam,Babu, Vemulapalli Sahithya Phani,Burri, David Raju
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- Heavy metal removing by modified bentonite and study of catalytic activity
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Due to the high hydrophobicity and surface area, clays are efficient adsorbents for the removal of liquid impurities and purification of gases when they are modified. In this work, bentonite was modified with imidazole and imidazolium groups and resulting clays were characterized by different techniques such as 1H NMR, 13C NMR, TEM, SEM, XPS, TG, and FT-IR. Applications of these clays were studied in the removal of Co, Cu, and Pb in the wastewater. Effects of contact time, pH, initial heavy metal ions concentration, and kinetic were investigated. The catalytic activity of the metals adsorbed by imidazole modified bentonite was studied in A3 coupling reactions of various amines, aldehydes, and alkynes.
- Kakaei, Saeed,Khameneh, Elham Sattarzadeh,Rezazadeh, Fardin,Hosseini, Majid Haji
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- Magnetically separable ZnFe2O4 nanoparticles: A low cost and sustainable catalyst for propargyl amine and NH-triazole synthesis
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The multicomponent reaction (MCR) strategy for the construction of important molecular scaffolds is in trending nowadays and among them, A3-coupling stands in a significant position. Aldehyde, amine and alkynes are coupled in this particular reaction via C-H activation process. Herein, we have reported zinc ferrite nanoparticles as magnetically separable heterogeneous catalyst for A3-coupling reaction with attractive attributes like excellent productivity, selectivity and better reusability. Moreover, the catalyst can also be effectively applied for the synthesis of various NH-triazoles with quantitative yields of the products. A plausible mechanism has been proposed for the synthesis of NH-triazoles followed by validation with computational study.
- Bordoloi, Ankur,Chetia, Swadhin,Garg, Anirban,Guha, Ankur Kanti,Hazarika, Roktopol,Kalita, Amlan Jyoti,Kulshrestha, Akshay,Kumar, Arvind,Phukan, Parmita,Sarma, Diganta
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- Copper modified spherical MCM-41 nano particles: An efficient catalyst for the three-component coupling of aldehydes, amines and alkynes in solvent-free conditions
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Cu-MCM-41 nano particles have been shown to effectively catalyze the multi-component synthesis of propargylamines by the reaction of aldehydes, amines, and alkynes (A3coupling) effectively at 100 °C under solvent-free conditions. Spherical Cu-M
- Abdollahi-Alibeik, Mohammad,Moaddeli, Ali
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- Fibroin-functionalized magnetic carbon nanotube as a green support for anchoring silver nanoparticles as a biocatalyst for A3 coupling reaction
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Novel and powerful fibroin-functionalized magnetic carbon nanotube–supported silver nanoparticles (CNT–Fe3O4–fibroin–Ag) were successfully synthesized as a nontoxic and inexpensive biocatalyst. The structure of the organic–inorganic
- Akbarzadeh, Parisa,Koukabi, Nadiya
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- Solvent-free synthesis of propargylamines via A3 coupling reaction and organic pollutant degradation in aqueous condition using Cu/C catalyst
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The present report focuses on the efficient and operationally simple synthesis of biomass-derived carbon as support to immobilize copper particles as a catalyst for the one-pot synthesis of propargylamines from furfural via the A3 coupling reaction. This new catalyst showed remarkable catalytic performance leading to a 97% yield within 5 h at 80 °C using 5 mg (0.0022 mmol Cu) of Cu/C catalyst under solvent-free condition. Moreover, nitro-substituted compounds such as 4-nitrophenol (4-NP) are highly toxic and not easily degradable. Hence, a quick and effective method is required to neutralize these toxic compounds. The synthesized active support Cu/C catalyst having various electron-donating groups containing small amounts of Cu plays an essential role in the catalytic reduction of 4-NP (0.1 g). Using only 3 mg (0.0013 mmol Cu) of Cu/C catalyst and NaBH4 (10 mmol), a 99% yield (100% selectivity) in the aqueous condition at 25 °C was achieved. The catalytic reduction follows the pseudo-first-order kinetics with reaction rate constant of 0.028 s?1. Moreover, results demonstrate that the Cu/C catalyst has superior catalytic activity due to the presence of electron-donating molecules such as O, S, and N atoms, which enable synergistic effect in enhancing the overall catalytic performance. Notably, the recoverability and recyclability of the synthesized catalyst were evaluated for up to four cycles, which confirmed its stability in these cycles.
- Rathod, Pramod V.,Puguan, John Marc C.,Kim, Hern
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- Gold nanoparticle stabilized dithiocarbamate functionalized magnetite carbon as promise clean nanocatalyst for A3-coupling organic transformation
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A novel, efficient, and core/shell nanosphere catalyst (Fe3O4@C-NHCS-Au0) was successfully synthesized with a movable magnetite core encapsulated in a carbon shell. It was modified using APTES (3-aminopropyltriethoxysilane
- Aghbash, Khadijeh Ojaghi,Alamgholiloo, Hassan,Pesyan, Nader Noroozi,Khaksar, Samad,Rostamnia, Sadegh
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- Efficient three-component coupling catalysed by mesoporous copper-aluminum based nanocomposites
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Traditional synthesis methods for propargylamines have several drawbacks. A recently developed alternative route is the so-called "A3 coupling" in which an alkyne, an aldehyde, and an amine are coupled together. Typically, these reactions are c
- Dulle, Jana,Thirunavukkarasu,Mittelmeijer-Hazeleger, Marjo C.,Andreeva, Daria V.,Shiju, N. Raveendran,Rothenberg, Gadi
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- Nafion NR50 catalyzed A3-coupling for the synthesis of propargylamines via C-H activation
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A one-pot, three-component coupling reaction of aldehydes, amines and alkyne (A3-coupling) via C-H activation using perflorinated resinsulphonic acid (Nafion NR50) as a recyclable and environmentally benign catalyst for the synthesis of proparg
- Kidwai,Jahan
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- CuPy2Cl2: A novel and efficient catalyst for synthesis of propargylamines under the conventional method and microwave irradiation
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CuPy2Cl2 is an efficient catalyst for the preparation of propargylamines via three-component coupling reaction of aromatic aldehydes, amines, and aromatic alkynes stirred at 95°C without using any solvent to afford the corresponding products in good yields. The reaction mixture was irradiated at 450 W in a microwave oven to furnish the expected products in excellent yields. Copyright Taylor & Francis Group, LLC.
- Madhav, J. Venu,Kuarm, B. Suresh,Someshwar,Rajitha,Reddy, Y. Thirupathi,Crooks, Peter A.
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- Comparison of the catalytic activity of gold nanoparticles supported in ceria and incarcerated in styrene copolymer
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The catalytic activity of gold nanoparticles supported on nanoparticulated ceria or incarcerated in a styrene copolymer has been compared for three general gold catalyzed reactions, namely the aerobic benzylamine and aniline oxidations and for phenylacetylene-aminebenzaldehyde coupling. Remarkable differences between the activity of both catalysts were observed.
- Perez, Yolanda,Aprile, Carmela,Corma, Avelino,Garcia, Hermenegildo
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- Disproportionation route to monodispersed copper nanoparticles for the catalytic synthesis of propargylamines
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By taking advantage of the coordination between a monovalent Cu+ precursor and trioctylphosphine, monodisperse Cu nanoparticles were synthesized via a disproportionation reaction. A Cu@SiO2 nanocatalyst was formed by supporting Cu na
- Guo, Huizhang,Liu, Xiang,Xie, Qingshui,Wang, Laisen,Peng, Dong-Liang,Branco, Paula S.,Gawande, Manoj B.
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- One-Pot Preparation of Propargylamines Catalyzed by Heterogeneous Copper Catalyst Supported on Periodic Mesoporous Organosilica with Ionic Liquid Framework
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Copper supported on periodic mesoporous organosilica (PMO) with alkylimidazolium frameworks is a highly efficient and recoverable catalyst for the preparation of propargylamines through the three-component coupling reaction of aldehydes, alkynes, and amin
- Gholinejad, Mohammad,Karimi, Babak,Aminianfar, Afsaneh,Khorasani, Mojtaba
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- Gold nanoparticles supported on mercaptoethanol directly bonded to MCM-41: An efficient catalyst for the synthesis of propargylamines
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Mercaptofunctionalized MCM-41 (MCM-SH) was obtained via reaction of MCM-chloride with mercaptoethanol. Then, gold nanoparticles supported on MCM-SH (Au@HS-MCM nanocomposite) were prepared by chemical reduction of HAuCl4 by NaBH4. The
- Feiz, Afsaneh,Bazgir, Ayoob
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- One-pot three-component synthesis of propargylamines using an efficient and reusable copper bio-functionalized magnetic graphene oxide nanocomposite
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In this work, magnetic graphene oxide was produced through chemical oxidation of the graphite powder, exfoliation under ultrasonic waves and then magnetization in the presence of ion salts. Magnetic graphene oxide was functionalized with cysteine and used
- Rafiee, Fatemeh,Khavari, Parvaneh
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- A green approach to the synthesis of Ag doped nano magnetic γ-Fe2O3@SiO2-CD core-shell hollow spheres as an efficient and heterogeneous catalyst for ultrasonic-assisted A3 and KA2 coupling reactions
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Using a green approach and ultrasonic-assisted template-free five-step process, a novel heterogeneous catalyst, γ-Fe2O3@SiO2-CD/Ag hollow spheres (h-Fe2O3@SiO2-CD/Ag), was fabricated. The d
- Sadjadi,Malmir,Heravi
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- Heterocyclic thiolates and phosphine ligands in copper-catalyzed synthesis of propargylamines in water
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The product obtained by reaction of deprotonation of 2-mercaptobenzothiazole or methimazole (2-mercapto-1-methylimidazole) with copper iodide in the presence of tertiary phosphines, PR2R' (R = R' = cyclohexyl; R = R' = phenyl; R = phenyl, R' = methyl) showed high catalytic activity in A3 coupling of a series of aldehydes with phenylacetylene and piperidine, yielding propargylamines. An investigation into the nature of active species carried out mainly by electrospray ionization mass spectrometry (ESI-MS) techniques underscores a crucial role played by organosulfur and organophosphorus compounds in the generation of active species responsible for these reactions. The coupling reactions were successfully carried out at low catalyst loadings in water/THF (20:1) and in relatively short reaction times. The scope of the reaction was also investigated with 20 examples.
- Neshat, Abdollah,Gholinejad, Mohammad,Afrasi, Mahmoud,Mastrorilli, Piero,Todisco, Stefano,Gilanchi, Shirin,Osanlou, Farzane
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- Nano-size ZnS: A novel, efficient and recyclable catalyst for A 3-coupling reaction of propargylamines
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Nano-size ZnS was prepared by a simple, economic and elegant chemical bath deposition technique and characterized by using SEM, TEM, XRD, and EDAX techniques. Prepared nano-size ZnS was found to be highly efficient novel heterogeneous catalyst for A3-coupling reaction of Propargylamines (4a-4l) using various aldehydes, amines and terminal alkyne groups through CH activation. The catalyst was recycled more than eight consecutive cycles and reused in the subsequent reactions without any loss in its activity. The developed protocol offers efficient synthesis of diverse propargylamines without using co-catalyst and any other activator, high catalytic activity and short reaction times were obtained when compared to other metal ion and/or metal oxide catalysts.
- Eagalapati, Nageswar Pandit,Rajack, Abdul,Murthy
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- Gold Nanoparticles Supported on Polyacrylamide Containing a Phosphorus Ligand as an Efficient Heterogeneous Catalyst for Three-Component Synthesis of Propargylamines in Water
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Gold nanoparticles supported on a polyacrylamide containing a phosphinite ligand have been synthesized and characterized using different techniques such as TEM, SEM, EDX, XPS, and solid UV analyses. The new material was successfully applied as a heterogen
- Gholinejad, Mohammad,Hamed, Fatemeh,Nájera, Carmen
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- Layered double hydroxide-supported gold catalyst for three-component aldehyde-amine-alkyne coupling
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A three-component coupling of aldehydes, amines and an alkyne to generate propargylic amines in nearly quantitative yields, using a layered double hydroxide-supported gold (LDH-AuCl4) catalyst is described. Both aromatic and aliphatic aldehydes
- Kantam, M. Lakshmi,Prakash, B. Veda,Reddy, Chinta Reddy Venkat,Sreedhar
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- Palladium(II) pyridoxal thiosemicarbazone complexes as efficient and recyclable catalyst for the synthesis of propargylamines by a three‐component coupling reactions in ionic liquids
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The palladium(II) complexes (1 and 2) were obtained from the reaction of [PdCl2(PPh3)2] with the tridentate Schiff base ligands, pyridoxal thiosemicarbazone (L1), and pyridoxal N-methyl thiosemicarbazone (L
- Manikandan, Rajendran,Anitha, Panneerselvam,Viswanathamurthi, Periasamy,Malecki, Jan Grzegorz
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- Silver chloride supported on Vitamin B1 -Organometallic magnetic catalyst: synthesis, density functional theory study and application in A3-coupling reactions
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A highly efficient Fe3O4@VitB1–Ag(I) magnetic catalyst has been obtained using surface modification of Fe3O4. To this end, silver chloride was immobilized on Fe3O4 nanoparticles
- Esfandiary, Naghmeh,Pazoki, Farzane,Nakisa, Athar,Azizi, Kobra,Radfar, Iman,Heydari, Akbar
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- Nanocrystalline magnesium oxide stabilized gold nanoparticles: An advanced nanotechnology based recyclable heterogeneous catalyst platform for the one-pot synthesis of propargylamines
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A simple and elegant synthesis of gold nanoparticles via counter ion stabilization of AuCl4- on nanocrystalline magnesium oxide support followed by sodium borohydride reduction is described here. A thorough characterization of the re
- Layek, Keya,Chakravarti, Rajashree,Lakshmi Kantam,Maheswaran,Vinu, Ajayan
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- Multifunctional phosphine stabilized gold nanoparticles: An active catalytic system for three-component coupling reaction
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Multifunctional phosphine based ligands, 1,1,1- tris(diphenylphosphinomethyl)ethane [CH3C(CH2 PPh 2)3][P3] and 1,1,1- tris(diphenylphosphinomethyl)ethane trisulphide [CH3C(CH 2P(S)Ph2)3][P3S3] have been introduced to stabilize Au°-nanoparticles having small core diameter and narrow size distribution. The Au°-nanoparticles were synthesized by the reduction of HAuCl4 precursor with NaBH4 in the presence of ligand P3 or P3S3 using two phases, one pot reaction at room temperature. The Au°-nanoparticles exhibit face centered cubic (fcc) lattice having different crystalline shape i.e., single crystallite stabilized by P3 while P3S3 forms decahedral shapes. Surface plasmon bands at ~520 nm and TEM study indicate particle size below 2 and 4 nm for Au°-nanoparticles stabilized by P3 and P3S3 respectively, which are attributable to the stronger interaction of Au° (Soft) with P (Soft) than Au° (Soft) with S (less Softer than P). Au°-nanoparticles stabilized by P3S3 shows higher thermal stability than that of P3. The synthesized Au°-nanoparticles serve as an efficient catalyst for one-pot, three-component (A3) coupling of an aldehyde, an amine and an alkyne via C H alkyne-activation to synthesize propargylamines (85-96%) without any additives and precaution to exclude air. Copyright
- Borah, Bibek Jyoti,Borah, Subrat Jyoti,Dutta, Dipak Kumar
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- Acridine based (S,N,S) pincer ligand: Designing silver(i) complexes for the efficient activation of A3 (aldehyde, alkyne and amine) coupling
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Complexes [AgL(NO3)CH3CN](1) and [AgLNO3] (2) were formed on reacting AgNO3 with L in acetonitrile for 12 h (at room temperature) and 24 h (at 90 °C), respectively, where L is a (S,N,S) pincer ligand, 4,5-bis(ph
- Prakash, Om,Joshi, Hemant,Kumar, Umesh,Sharma, Alpesh K.,Singh, Ajai K.
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- Gold(III) salen complex-catalyzed synthesis of propargylamines via a three-component coupling reaction
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Propargylamines have been synthesized by a gold(III) salen complex-catalyzed three-component coupling reaction of aldehydes, amines, and alkynes in water in excellent yields at 40 °C. With chiral prolinol derivatives as the amine component, excellent diastereoselectivities (up to 99:1) have been attained. This coupling reaction has been applied to the synthesis of propargylamine-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. Cytotoxicities with IC50 values up to 1.1 μM against a human hepatocellular carcinoma cell line (HepG2) were exhibited by these artemisinin derivatives.
- Lo, Vanessa Kar-Yan,Liu, Yungen,Wong, Man-Kin,Che, Chi-Ming
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- Copper nanoparticles supported on starch micro particles as a degradable heterogeneous catalyst for three-component coupling synthesis of propargylamines
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Novel copper nanoparticles supported on starch micro particles (CuNPs@MS) were prepared successfully and characterized by SEM, EDX, TEM, SAED, TGA, XPS, and XRD analyses. The easily synthesized and thermally stable CuNPs@MS have been applied as a green, d
- Gholinejad, Mohammad,Saadati, Fariba,Shaybanizadeh, Shahram,Pullithadathil, Biji
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- Solvent-free synthesis of propargylamines catalyzed by an efficient recyclable ZnO-supported CuO/Al2O3 nanocatalyst
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An efficient nanocatalyst of ZnO-supported CuO/Al2O3 (CuO/ZnO/Al2O3 nanocatalyst) was prepared by the co-precipitation method and characterized by scanning electron microscopy, energy-dispersive X-ray spectrosco
- Sotoudehnia, Zohreh,Albadi, Jalal,Momeni, Ahmad Reza
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- Covalently Copper(II) Porphyrin Cross-Linked Graphene Oxide: Preparation and Catalytic Activity
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Abstract: In this study, copper(II)-coordinated 5,10,15,20-tetrakis(aminophenyl)porphyrin (CuPPh) as a macrocyclic copper complex was covalently linked to the surface of graphene oxide (GO–CuPPh). This covalently cross-linked catalyst was characterized with various analysis such as FT-IR, SEM, TEM, EDS, ICP, TGA and UV–Vis. All analysis confirm the successful covalently immobilization of CuPPh on the GO. Then, the activity of catalyst has been tested for the preparation of propargylamine derivatives by the reaction of different aldehydes/ketones various amines and phenylacetylene via A3 and KA2 coupling reactions. The catalytic system indicated great catalytic activity in this reaction and the yields of the products were good to marvelous. The results of this work are hoped to aid the establishment of new class of heterogeneous catalysts as the high performance and low-cost candidates for industrial applications. Graphical Abstract: [Figure not available: see fulltext.].
- Khojastehnezhad, Amir,Bakavoli, Mehdi,Javid, Ali,Khakzad Siuki, Mohammad Mehdi,Moeinpour, Farid
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- The silver salt of 12-tungstophosphoric acid: an efficient catalyst for the three-component coupling of an aldehyde, an amine and an alkyne
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A three-component coupling of an aldehyde, an alkyne and an amine to prepare propargylamines was performed using the silver salt of 12-tungstophosphoric acid (Ag3PW12O40) as a heterogeneous catalyst under mild reaction conditions in the absence of any co-catalyst. A variety of aldehydes and amines were converted to the corresponding propargylamines demonstrating the versatility of the reaction. The Ag3PW12O40 (AgTPA) catalyst was recovered quantitatively by a simple filtration and reused several times.
- Mohan Reddy,Seshu Babu,Suryanarayana,Sai Prasad,Lingaiah
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- Recyclable ZnO nano particles: Economical and green catalyst for the synthesis of A3 coupling of propargylamines under solvent free conditions
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Recyclable ZnO nano particles (ZnO NPs) provide an efficient and economic route for synthesis of multi component A3 coupling reaction of propargylamines under solvent free condition. It was found that without using co-catalyst and any other act
- Satyanarayana,Ramaiah, P. Atchuta,Murty,Chandra, M. Ravi,Pammi
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- Unprecedented one-pot multicomponent synthesis of propargylamines using Amberlyst A-21 supported CuI under solvent-free conditions
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Amberlyst A-21 supported CuI was found to be a highly efficient novel heterogeneous catalyst for the three-component reaction between amines, aldehydes and alkynes, commonly called A3-coupling. An environmentally benign, one-pot, A3-
- Bosica, Giovanna,Gabarretta, John
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- CuI@Sulfur-functionalized halloysite nanoclay: a novel recyclable catalyst for the ultrasonic-assisted synthesis of propargylamines: a combination of experimental and DFT simulation
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A novel heterogeneous catalyst, CuI supported on sulfur functionalized halloysite (CuI@HNTs-S), was designed and synthesized through functionalization of the halloysite nanoclay surface with 3-mercaptopropyl trimethoxysilane and subsequent immobilization of CuI. The catalyst was characterized by using various characterization techniques such as FTIR, SEM/EDS, XRD, ICP and TGA. The catalytic activity of CuI@HNTs-S for the synthesis of propargylamines through ultrasonic-assisted multi-component A3 coupling reaction of aldehydes, phenyl acetylene and amines was also studied. The results established that CuI@HNTs-S could efficiently catalyze the reaction to furnish the desired products in excellent yield and in short reaction time. Notably the catalyst was recyclable and could be recycled with slight loss of the catalytic activity for five reaction runs. Then, the ability of pristine HNTs and sulfur functionalized HNTs toward CuI grabbing was compared quantitatively using molecular simulation. Calculated energies confirmed better performance of HNTs-S toward CuI physisorption, which decreases its leaching during catalytic reaction. This result was experimentally confirmed by observing the superior recyclability and low copper leaching of CuI@HNTs-S compared to CuI@HNTs.
- Bahri-Laleh, Naeimeh,Sadjadi, Samahe
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- Tunable Prussian blue analogues for the selective synthesis of propargylamines through A3 coupling
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M1[Co(CN)6]2/3-type Prussian blue analogues (M1-Co PBAs) were studied as catalysts for the synthesis of propargylamines via A3 coupling of phenylacetylene, benzaldehyde and piperidine. Cu0.86/su
- Marquez, Carlos,Cirujano, Francisco G.,Van Goethem, Cédric,Vankelecom, Ivo,De Vos, Dirk,De Baerdemaeker, Trees
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- Eco-friendly magnetic clinoptilolite containing Cu(0) nanoparticles (CuNPs/MZN): as a new efficient catalyst for the synthesis of propargylamines via A3 and KA2 coupling reactions
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In this reaserch a new and eco-friendly magnetic catalyst for the synthesis of propargylamines is reported. Initial incorporation of Fe3O4 magnetic nanoparticles (MNPs) into the pores of the natural clinoptilolite zeolite followed by
- Khakzad Siuki, Mohammad Mehdi,Bakavoli, Mehdi,Eshghi, Hossein
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- Investigation into the Catalytic Performance of Cu(II) Supported Graphene Quantum Dots Modified NiFe2O4 as a Proficient Nano-Catalyst in the Synthesis of Propargylasmines
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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
- Monajjemifar, Soudabeh,Moeinpour, Farid,Mohseni-Shahri, Fatemeh S.
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- N-Heterocyclic carbene–copper complex supported on ionic liquid-modified graphene oxide: versatile catalyst for synthesis of (i) 1,2,3-triazole and (ii) propargylamine derivatives
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A N-heterocyclic carbene–copper complex grafted on graphene oxide with an ionic liquid framework was prepared. The synthesis of (i) 1,2,3-triazole derivatives by ‘Click reaction’ and (ii) propargylamine derivatives by ‘A3 coupling reaction’ in
- Dabiri, Minoo,Alavioon, Seyed Iman,Movahed, Siyavash Kazemi
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- Gold immobilized onto poly(ionic liquid) functionalized magnetic nanoparticles: A robust magnetically recoverable catalyst for the synthesis of propargylamine in water
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Supported gold(III) on poly(ionic liquid) coated on magnetic nanoparticles produced a highly active, stable, recoverable and high loading for the synthesis of propargylamines (A3 coupling reaction) under green conditions. The reaction of aldehy
- Moghaddam, Firouz Matloubi,Ayati, Seyed Ebrahim,Hosseini, Seyed Hassan,Pourjavadi, Ali
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- Synthesis and crystal structures of salen-type Cu(II) and Ni(II) Schiff base complexes: application in [3+2]-cycloaddition and A3-coupling reactions
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The synthesis of two new salen-type Schiff base complexes of the type [Cu(L)]·0.5H2O, 1, and [Ni(L)], 2, from the reaction of a 6,6′-[(1E,1′E)-(cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene)bis(3-(diethylamino)phenol)] salen-type Schiff base ligand (H2L) with Cu(OAc)2·H2O and Ni(OAc)2·4H2O in methanol at room temperature, respectively, is described. The complexes are isolated as coloured crystalline solids and characterized by elemental analysis, FT-IR spectroscopy, UV-visible spectroscopy and single crystal X-ray diffraction studies. The paramagnetic nature of complex 1, having giso = 2.076, was confirmed by EPR studies, which indicated a distorted square planar geometry of the complex. In contrast to this, the nickel complex was found to be diamagnetic in nature and it was additionally characterized by 1H NMR. The crystal structures of complexes 1 and 2 confirm the distorted square planar geometry of both the complexes. Complex 1 was found to be a better catalyst for the synthesis of a series of 5-substituted 1H-tetrazoles from nitriles and sodium azide via [3+2]-cycloaddition and for the A3-coupling reaction of aldehydes, secondary amines and terminal alkynes with a low catalyst loading (0.7 and 0.9 mol%, respectively) as compared to complex 2. Complex 1 is novel in the sense that, being a homogeneous catalyst, it can be recovered almost quantitatively in both reactions and recycled up to four times to afford good yields of the corresponding products.
- Agrahari, Bhumika,Layek, Samaresh,Ganguly, Rakesh,Pathak, Devendra D.
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- Functionalized Polystyrene Supported Copper(I) Complex as an Effective and Reusable Catalyst for Propargylamines Synthesis in Aqueous Medium
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Abstract: An efficient procedure for the one-pot synthesis of propargylamines is A3 coupling in which an alkyne, an aldehyde, and an amine are coupled together. Here, we report that polystyrene supported Cu(I) catalyst is excellent for A3 coupling in water without using any additives or hazardous organic solvents. The polystyrene supported Cu(I) catalyst was synthesized and its catalytic activity was also evaluated in the synthesis of propargylamines in oxidative A3-coupling reaction with benzyl alcohols instead of their aldehydes in water. This protocol offers several advantages such as high yields of the desired product, reaction in aqueous medium and recyclability of the catalyst. It gives well to excellent yields for a variety of substrates. As it acts as heterogeneous catalyst, it can be easily separated from the reaction mixture and reused without appreciable loss of activity. Graphical Abstract: Polymer supported copper catalyst, Cu-PS-ala, acts as a heterogeneous catalyst for the one pot synthesis of propargylamines via A3 coupling reaction in water using aldehydes or alcohols, amines and alkynes.[Figure not available: see fulltext.]
- Islam, Md. Mominul,Roy, Anupam Singha,Islam, Sk. Manirul
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- Amino acid ionic liquid bound copper Schiff base catalyzed highly efficient three component A3-coupling reaction
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Amino acid ionic liquid Schiff base derived from dl-threonine and salicylaldehyde was complexed with copper (II) ions and used as an efficient and reusable catalyst for multicomponent synthesis of propargylamines via A3 coupling of aldehydes, a
- Varyani, Manish,Khatri, Praveen K.,Jain, Suman L.
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- An efficient synthesis of propargylamines using a silica gel anchored copper chloride catalyst in an aqueous medium
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The design and development of a silica gel anchored copper chloride heterogeneous catalyst for the synthesis of propargylamines using an amine, an aldehyde, and an alkyne through C-H activation in water is described. Both aliphatic and aromatic aldehydes and amines are used for the reaction. The catalyst was recovered quantitatively by simple filtration and reused several times.
- Sreedhar,Surendra Reddy,Vamsi Krishna,Vijaya Babu
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- Amine-functionalized MIL-101(Cr) embedded with Co(II) phthalocyanine as a durable catalyst for one-pot tandem oxidative A3 coupling reactions of alcohols
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A novel porous postsynthetic-modified metal-organic framework (MIL-101(Cr)-NH2) was fabricated via covalent immobilization of cobalt(ii) phthalocyanine and characterized by a variety of techniques, including FTIR, XRD, TGA, SEM, EDS and ICP-OES
- Shaabani, Ahmad,Mohammadian, Reza,Hashemzadeh, Alireza,Afshari, Ronak,Amini, Mostafa M.
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- Synthesis, characterization, and application of zinc supported on ionic liquid‐based periodic mesoporous organosilica (Zn?PMO-IL) in A3-coupling reaction for the synthesis of propargylamines
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Abstract: The present paper shows the preparation of a highly porous periodic mesoporous organosilica (PMO) including the ionic liquid pore walls that supported with zinc ions onto PMO-IL (Zn?PMO-IL). Moreover, the material was characterized using field e
- Allahgholipour, Seyedeh Leila,Baharfar, Robabeh
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- Core-shell iron oxide@cathecol-polymer@palladium/copper nanocomposites as efficient and sustainable catalysts in cross-coupling reactions
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Magnetic core-shell Fe2O3@polymer-Pd/Cu nanocomposites (NCs) were developed as efficient and sustainable nanocatalysts for cross-coupling reactions. The designed NCs consisted of three components: i) a magnetic core (Fe2O3 nanoparticle), which allowed the recovery and reuse of the NCs, enhancing thus their attractiveness as green catalysts; ii) a catechol-based polymer coating, chosen because of its strong chelating ability towards metal ions, and its potential to be obtained from biomass (lignin depolymerization); and iii) catalytically active metal nanoparticles (Pd and Cu NPs) immobilized via in situ formation onto the polymeric shell. As-prepared Pd-based NCs successfully catalyzed Suzuki-Miyaura cross-coupling reactions, achieving yields between 87% and 97% in only 20–40 min depending on the aryl halides and boronic acid derivatives. Similarly, Cu-based NCs exhibited a quite good catalytic efficiency (> 80%) in the synthesis of propargylamines via A3 coupling reaction of phenylacetylene with various aldehydes and amines. Importantly, these NCs presented a good reusability, without significant decrease in efficiency after several cycles. However, the major advantage of the designed NCs is the lower Pd or Cu content (1.5 wt% and 2.6 wt%, respectively) as compared to most of the reported similar catalysts (between 3 – 6 wt% for Pd and > 5 wt% for Cu), which is a key challenge in view of developing cost-effective and environment-friendly catalysts while maintaining a high efficiency.
- Ostovar, Somayeh,Rezvani, Alireza,Luque, Rafael,Carrillo-Carrión, Carolina
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- Nano-NiZr4(PO4)6 as a superior catalyst for the synthesis of propargylamines under ultrasound irradiation
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An easy and rapid method for the synthesis of propargylamines has been achieved through a three-component reaction of phenylacetylene, aromatic aldehydes, and morpholine or piperidine using nano-NiZr4(PO4)6 under ultrasound irradiation. Atom economy, a wide range of products, excellent yields in short times, reusability of the catalyst, and low catalyst loading are some of the important features of this protocol.
- Shahbazi-Alavi, Hossein,Nazemzadeh, Seyed Hadi,Ziarati, Abolfazl,Safaei-Ghomi, Javad
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- Iron oxide modified with pyridyl-triazole ligand for stabilization of gold nanoparticles: An efficient heterogeneous catalyst for A3 coupling reaction in water
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Fe3O4 nanoparticles were modified with pyridyl-triazole ligand and the new magnetic solid was applied for the stabilization of very small and uniform gold nanoparticles. The resulting magnetic material, Fe3O4@PT
- Gholinejad, Mohammad,Zareh, Fatemeh,Najera, Carmen
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- Solvent-free coupling of aldehyde, alkyne, and amine over a versatile catalyst: Ag-functionalized mesoporous S, P-doped g-C3N4
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In the present study, we introduce mesoporous g-C3N4/Ag co-doped with P and S which was designed and acquired by using mesoporous silica (SBA-15) as a hard templating agent and thiourea and chitosan phosphate as the dopants. The prep
- Bagherzade, Azra,Nemati, Firouzeh
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- Ag2CO3-catalyzed efficient synthesis of internal or terminal propargylicamines and chalcones via A3-coupling under solvent-free condition
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Several simple, fast and practical protocols have been developed to synthesize internal or terminal propargylamines and chalcones via A3-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag2CO3 under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated. Furthermore, plausible mechanisms for the synthesis of different products have been proposed.
- Li, Ningbo,Xu, Shitang,Wang, Xueyan,Xu, Li,Qiao, Jie,Liang, Zhiwu,Xu, Xinhua
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p. 3993 - 3997
(2021/05/31)
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- Magnetic AgNPs/Fe3O4@chitosan/PVA nanocatalyst for fast one-pot green synthesis of propargylamine and triazole derivatives
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A new green magnetic nanocatalyst was introduced for one-pot fast synthesis of propargylamine and triazole derivatives. Chitosan bio-polymeric chains were functionalized with polyvinyl alcohol (PVA) and then templated with silver nanoparticles (AgNPs) and magnetic Fe3O4to obtain the AgNPs/Fe3O4@chitosan/PVA composite. Spectral and analytical examinations were conducted using X-ray diffraction, Fourier transform-infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, vibrating sample magnetometry, and energy-dispersive X-ray spectroscopy for understanding the structural, morphological and physiochemical features of the obtained magnetic nanocomposite and the homogeneous distribution of AgNPs on the surface of nanocomposite with Fe3O4nucleus. The AgNPs/Fe3O4@chitosan/PVA nanocatalyst was used in the synthesis of biologically active compounds such as propargylamine and triazole derivatives through multicomponent A3-coupling and click reactions. The catalyzed products were obtained in high yields under ambient conditions through a low-cost, facile, one-pot, and environmentally friendly protocol. The reusability of the heterogeneous magnetic catalyst was also confirmed up to six cycles without any significant loss in the catalytic activity, as well as easy separation of the catalyst.
- Amini, Abbas,Cheng, Chun,Darroudi, Mahdieh,Ghasemi, Kousar,Gupta, Anju R.,Rahimi, Marjan,Rouh, Hossein
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supporting information
p. 16119 - 16130
(2021/09/22)
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- A core-shell superparamagnetic metal-organic framework: a recyclable and green catalyst for the synthesis of propargylamines
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In this research, an efficient and reusable magnetic metal-organic framework (MOF) catalyst has been developed with a core-shell structure. Afterwards, the chemical and physical structures of the catalyst have been confirmed completely and successfully by
- Arefi, Elham,Khojastehnezhad, Amir,Shiri, Ali
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p. 21342 - 21349
(2021/12/09)
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- Amino acid-assisted ferrite/MOF composite formation for visible-light induced photocatalytic cascade C=C aerobic oxidative cleavage functionalization
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Due to their high variability and extraordinary features, the MOF-based nanomaterials are regarded as promising photocatalysts in organic reactions. In this study, the magnetic Co-MOF-based nanocomposite (denoted by Cys-CoFe/HK) was prepared through a facile sonochemical method. The composite design was based on the integration and synergy of the desired properties of the components, i.e., optical properties of the magnetic substrate and its separation capability, desirability of metal-organic framework to promote A3-coupling reaction, and use of cysteine ??amino acid as a natural modifier to modify nanoparticles and make an efficient charge transfer. The information about their structural features was obtained using various characterization methods. In addition to the high photocatalytic activity of the developed composite in the aerobic oxidative propargylic functionalization of styrene under visible light illumination, the composite showed a high capability to interact with a wide range of amines, styrene, and terminal alkynes as participants in A3-coupling reaction. Furthermore, the developed catalyst demonstrated high accessibility of active sites, reusability, and magnetic properties, which accelerated the efficiency of the A3-coupling reaction. Moreover, the mechanistic investigations, including trapping experiments, confirmed the presence of superoxide radical (O2●[sbnd]) and holes (h+) as essential species to perform the considered reaction. Our methodical approach to the fabrication of Cys-CoFe/HK composite provided optimal conditions for improving previous studies and thus the industrial processes in environmentally sensitive areas.
- Al-Mubaddel, Fahad S.,Gavinehroudi, Reza Ghahremani,Heydari, Akbar,Karimi, Meghdad,Mahjoub, Alireza,Marzouki, Riadh,Mohebali, Haleh,Ouni, M. H. El,Sadeghi, Samira
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- Gold nanoparticles stabilized by PEG-tagged imidazolium salts as recyclable catalysts for the synthesis of propargylamines and the cycloisomerization of γ-alkynoic acids
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We report the synthesis of PEGylated imidazolium (bromide and tetrafluoroborate) and tris-imidazolium (bromide) salts containing triazole linkers, and their use as stabilizers for the preparation of water-soluble gold nanoparticles by reduction of tetrachloroauric acid with sodium borohydride. The nanomaterials have been characterized. The X-Ray Photoelectron Spectroscopy (XPS) indicated the presence of Au(i) and Au(0) species, the oxidized form being more abundant in the nanomaterial derived from the tris-imidazolium bromide. The catalytic activity of these gold nanoparticles has been proved in the A3 coupling between carbonyl compounds, terminal alkynes and amines to afford propargylamines, and in the cycloisomerization of γ-alkynoic acids to enol lactones. The nanomaterial derived from the PEG-tagged tris-imidazolium bromide provided the best performance and it has been recycled in both reactions (up to four and six runs) taking advantage of its solubility properties.
- Bernardo, Laura,Fernández, Guillem,Pleixats, Roser,Villanueva, Ana
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p. 6130 - 6141
(2020/05/13)
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- Study on the A3-coupling reaction catalyzed by readily available copper-containing minerals. Synthesis of propargylamines
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The highly atom efficient three-component reaction of aldehydes, secondary amines and acetylenes to form propargylamines (A3-coupling) has been studied with twelve readily available copper-containing minerals. It was found that the reaction could easily be performed in the presence of malachite, brochantite, chrysocolla and azurite in toluene at reflux. The desired products were obtained in good to excellent yields.
- Milen, Mátyás,Gy?rke, Gábor,Dancsó, András,Volk, Balázs
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supporting information
(2020/01/13)
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- Copper-based catalysts derived from salen-type ligands: Synthesis of 5-substituted-1: H-tetrazoles via [3+2] cycloaddition and propargylamines via A3-coupling reactions
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Base-metal copper(ii) complexes derived from unsymmetrical salen-type ligands were designed and synthesized using ligands L1H to L4H in moderate yield. The synthesized unsymmetrical ligands L1H to L4H and the corresponding copper complexes (1-4) were characterized by UV-visible, IR and ESI-MS spectroscopic studies. Molecular structures of complexes 1, 2 and 4 were determined by X-ray crystallography. Copper complexes 1-4 were employed as catalysts for [3+2] cycloaddition and A3-coupling reactions. The mutual approach of salen-type ligands and metals via active participation of ligands allow to achieve the catalytic reactions. Reaction pathways were proposed and possible intermediate species during the catalytic cycle were successfully characterized by ESI-MS spectroscopic studies. This journal is
- Singh, Anshu,Maji, Ankur,Mohanty, Aurobinda,Ghosh, Kaushik
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p. 18399 - 18418
(2020/11/13)
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- 1D Fe3O4&at;CuSiO3 composites catalyzed decarboxylative A3-coupling for propargylamine synthesis
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Highly active and stable magnetic copper catalysts were successfully achieved by magnetic induced St?ber method and subsequent hydrothermal reaction with copper ions in alkaline condition. The high content of Cu2+ as well as the unique structures of hierarchical copper silicate in the as-prepared catalysts endowed their outstanding catalytic performance. Efficient decarboxylative A3-coupling of α-keto acid, amine and alkyne was realized with the low Fe3O4&at;CuSiO3 loading. A range of propargylamines were produced in good to excellent yields under solvent-free condition. Moreover, the catalyst can be easily separated from the final organic product with an external magnet. Also, this kind of catalyst could be recycled up to six times while maintaining its activity.
- Cao, Tiantian,Feng, Huangdi,Li, Huiqiong,Miao, Teng,Wang, Fang,Zhang, Min
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p. 1558 - 1563
(2020/07/30)
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- Metal ion exchange in Prussian blue analogues: Cu(ii)-exchanged Zn-Co PBAs as highly selective catalysts for A3 coupling
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The occurrence of metal ion exchange in Zn3[Co(CN)6]2 and Cu3[Co(CN)6]2 Prussian blue analogues (Zn-Co and Cu-Co PBAs) was demonstrated for the first time. While Cu(ii) ion exchange easily occurs in Zn-Co PBA, the exchange of Cu(ii) atoms in Cu-Co PBA by Zn(ii) proved to be more difficult. At low to medium Cu(ii) loadings, the catalytic activity of the exchanged PBAs for the A3 coupling reaction of benzaldehyde, piperidine and phenylacetylene was higher than that of the bimetallic PBAs and that of multi metal PBAs of similar composition prepared by co-precipitation. This result showcases the benefits of the ion exchange process as a preparation method of PBA catalysts, since it is believed to lead to the incorporation of the desired metal in a more accessible position for reactant molecules. At higher Cu(ii) loadings, ion exchange with Cu(CH3COO)2·H2O also resulted in co-incorporation of CH3COO-. This incorporation considerably boosted the catalytic activity of the PBAs by providing a basic function that facilitates the C-H activation of phenylacetylene. The most active of the studied PBAs, catallytically outperforms other Cu(ii) based A3 coupling catalysts and completely suppresses the activity for the homocoupling of phenylacetylene, even under oxidative conditions. Furthermore, the basicity of the PBAs was investigated in the nitroaldol (Henry) reaction, where a clear effect of the presence of CH3COO- was observed. The CH3COO- containing PBAs exhibited an activity three times higher than the rest of the PBAs. The presence of the basic CH3COO- groups represents the first case of basic functionalization of PBAs.
- Marquez, Carlos,Cirujano, Francisco G.,Smolders, Simon,Van Goethem, Cédric,Vankelecom, Ivo,De Vos, Dirk,De Baerdemaeker, Trees
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supporting information
p. 3946 - 3954
(2019/03/26)
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- Multi-component reaction-functionalized chitosan complexed with copper nanoparticles: An efficient catalyst toward A3 coupling and click reactions in water
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A novel bio-nanocomposite nanocatalyst with highly dispersed particles is synthesized through covalent functionalization of chitosan biopolymer by the multicomponent reaction (MCR) strategy. Surface functionalization of chitosan through MCR is led to the
- Shaabani, Ahmad,Shadi, Mehrdad,Mohammadian, Reza,Javanbakht, Siamak,Nazeri, Mohammad Taghi,Bahri, Fereshteh
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- Expeditious and highly efficient synthesis of propargylamines using a Pd-Cu nanowires catalyst under solvent-free conditions
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A heterogeneous Pd-Cu NWs-catalyzed expeditious and solvent-free synthesis of propargylamines via A3-coupling of aldehydes, alkynes, and amines has been proposed. A wide range of aldehydes, alkynes and amine substrates undergo A3-coupling to produce propargylamines in good to excellent yields with good functional tolerance, such as that towards alkoxy, hydroxy, C-X (X?=?F, Cl, Br) as well as amide and C=C bonds. Furthermore, the catalyst could be recovered easily and reused for at least 5?cycles without showing significant loss of catalytic activity.
- Yi, Rongnan,Wang, Zheng-Jun,Liang, Zhiwu,Xiao, Min,Xu, Xinhua,Li, Ningbo
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- MIL-101 supported highly active single-site metal catalysts for tricomponent coupling
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Metal-organic frameworks with regular pore structures provide powerful platforms for the design of single-site metal catalysts for chemical transformation. In this paper, we develop a facile, stable and recyclable MOF-supported Cu(II) catalyst, MIL-101-SO3Cu. It shows extremely high activity for the A3 coupling of alkynes, aldehydes and amines. The turnover frequency can reach 6.8 × 105 h?1 under neat conditions, which is the highest so far reported for the reaction. The high activity is because the specific structure of the MIL-101-SO3 support enables a single-site dispersion and an unhindered open environment for the metal ion. MIL-101-SO3Cu also exhibits high activity for the one-pot cascade reactions combining A3 coupling and 5-endo-dig cyclization.
- Sun, Weng-Jie,Gao, En-Qing
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p. 110 - 116
(2018/11/10)
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- From Zn(II) to Cu(II) framework via single-crystal to single-crystal metathesis with superior gas uptake and heterogeneous catalytic properties
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In this work, a Zn(II) framework, {[Zn2(L)4(H2O)4]·(7DMF)(7H2O)}n (1Zn), has been synthesized using a bent tetracarboxylic acid ligand (H4L). The structure of 1Zn contains [Zn2(COO)4] paddle-wheel secondary building units with axial sites occupied by water molecules. Interestingly, the isostructural Cu(II) framework {[Cu2(L)4(H2O)4]·(7DMF)(7H2O)}n (1Cu) has been obtained via single-crystal to single-crystal metathesis reaction. The activated 1Cu (denoted as a1Cu; a stands for activated) has open coordination sites. This species showed enhanced CO2 adsorption and heterogeneous catalytic properties for the Hantzsch coupling reaction involving condensation of an aldehyde with ethyl acetoacetate and ammonium acetate to produce 1,4-dihydropyridines, and three-component coupling of amines, aldehydes and alkynes to generate propargylic amines with high efficiency.
- Gupta, Mayank,De, Dinesh,Tomar, Kapil,Bharadwaj, Parimal K.
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p. 925 - 934
(2018/08/06)
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- Efficient method for the synthesis of propargylamines using a biomaterial containing copper nanoparticles as impressive and reusable nanocatalyst
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Preparation and catalytic performance of nanosized copper particles supported on expanded corn starch (ECS) was investigated. The catalyst was characterized by inductively coupled plasma optical emission spectrometry (ICP-OES), X-ray powder diffraction (X
- Saadati, Fariba,Gholinejad, Mohammad,Janmohammadi, Hadiseh,Shaybanizadeh, Shahram
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- New method for synthesis of propargylamine compound
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The invention relates to a new method for synthesis of a propargylamine compound. The method is characterized by: under a solvent-free condition, taking Ag2CO3 as the catalyst, using terminal alkyne,aldehyde and amine as starting materials, and carrying out efficient and rapid reaction at 60-110DEG C by "one-pot method" to synthesize a propargylamine compound.
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Paragraph 0017-0018
(2018/07/15)
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- Preparation of Ag-doped g-C3N4 Nano Sheet Decorated Magnetic γ-Fe2O3@SiO2 Core–Shell Hollow Spheres through a Novel Hydrothermal Procedure: Investigation of the Catalytic activity for A3, KA2 Coupling Reactions and [3?+?2] Cycloaddition
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Taking advantageous of both g-C3N4 and magnetic core-shell hollow spheres, for the first time a heterogeneous and magnetically separable hybrid system was prepared through a novel and simple hydrothermal procedure and used for immobilization of bio-synthesized Ag(0) nanoparticles. The hybrid system was fully characterized by using SEM/EDS, FTIR, VSM, TEM, XRD, TGA, DTGA, ICP-AES, BET and elemental mapping analysis. The catalytic utility of the obtained system, h-Fe2O3@SiO2/g-C3N4/Ag, for promoting ultrasonic-assisted A3, KA2 coupling reactions and [3?+?2] cycloaddition has been confirmed. The results established that the catalyst could efficiently catalyze the reaction to afford the corresponding products in high yields in short reaction times. The reusability study confirmed that the catalyst could be recovered and reused for at least five reaction runs with only slight loss of the catalytic activity. The hot filtration test also proved low silver leaching, indicating the heterogeneous nature of the catalysis.
- Sadjadi, Samahe,Malmir, Masoumeh,Heravi, Majid M.
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- Green bio-based synthesis of Fe2O3@SiO2-IL/Ag hollow spheres and their catalytic utility for ultrasonic-assisted synthesis of propargylamines and benzo[b]furans
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A novel magnetic hybrid system containing nano-magnetic Fe2O3 hollow spheres, silica shell, [pmim]Cl ionic liquid and silver nanoparticles was synthesized and characterized. The silver nanoparticles were prepared via biosynthesis usi
- Sadjadi, Samahe,Heravi, Majid M.,Malmir, Masoumeh
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- Gold Nanoparticles Supported on Imidazole-Modified Bentonite: Environmentally Benign Heterogeneous Catalyst for the Three-Component Synthesis of Propargylamines in Water
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Gold nanoparticles supported on imidazole-modified bentonite, Bent@Im@Au NPs, has been developed for the first time as an effective heterogeneous catalyst for the synthesis of propargylamines under mild reaction conditions in water at a loading of 0.07 mol % of Au. Various techniques such as X-ray diffraction, high-resolution transmission electron microscopy, Fourier transform infrared spectroscopy, and element mapping by scanning electron microscopy were used to determine the physicochemical properties of the catalysts. The new gold catalyst was found to be highly active providing high to excellent yields of A3 coupling products via the reactions of various aldehydes, having electron-withdrawing as well as electron-donating substituents, with different amines and alkynes. The catalysts can be easily recovered and reused without significant loss of activity and the recycled catalyst was characterized.
- Gholinejad, Mohammad,Bonyasi, Reza,Najera, Carmen,Saadati, Fariba,Bahrami, Maedeh,Dasvarz, Neda
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p. 431 - 438
(2018/06/04)
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- N-Heterocyclic Carbene-Protected Ag Nanoparticles Immobilized on Polyacrylonitrile Fiber as Efficient Catalysts for a Three-Component Coupling Reaction
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Metal nanoparticles (NPs) are routinely stabilized by the introduction of capping agents or their distribution on supports. In this context, we report the preparation and characterization of N-heterocyclic carbene (NHC)-stabilized silver NPs supported on
- Cao, Jian,Tian, Hongqi
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p. 1561 - 1569
(2018/06/26)
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- Nano Ag-doped magnetic-Fe3O4@mesoporous TiO2 core–shell hollow spheres: synthesis and enhanced catalytic activity in A3 and KA2 coupling reactions
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Abstract: Nano Ag-doped Fe3O4@mesoporous TiO2 core–shell hollow spheres (h-Fe3O4@m-TiO2/Ag) were efficiently prepared. They were fully characterized by FT-IR, FE-SEM, EDX, ICP, TGA, XRD, and BET methods. In addition, their magnetic properties were determined by means of the VSM method. Also, the ρshell of the prepared hollow Fe3O4 micro-particles was calculated, being found just slightly lighter than that of solid sphere-like Fe3O4. The catalytic activity of this novel catalyst system was successfully examined as a novel catalyst system in A3 coupling reactions (aldehyde?+?amine?+?acetylene). This highly active magnetic catalyst was easily separated using an external magnet and re-used in five consecutive runs in the model reaction without appreciable loss of its catalytic activity. Graphical abstract: [Figure not available: see fulltext.].
- Elhampour, Ali,Nemati, Friuozeh,Heravi, Majid M.
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p. 1793 - 1805
(2017/09/26)
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- Efficient multicomponent synthesis of propargylamines catalyzed by copper nanoparticles supported on metal-organic framework derived nanoporous carbon
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Cu nanoparticles were deposited on nanoporous carbon, MOF-5-C, which was fabricated by direct carbonization of MOF-5 without any additional carbon sources. The as-obtained catalyst (Cu@MOF-5-C) exhibited high catalytic activity due to the high surface area as well as hierarchical pores of MOF-5-C, and the synergetic interaction between the metal nanoparticles and support.
- Cheng, Saisai,Shang, Ningzhao,Feng, Cheng,Gao, Shutao,Wang, Chun,Wang, Zhi
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- Assembling Porphyrins into Extended Network Structures by Employing Aromatic Dicarboxylates: Synthesis, Metal Exchange, and Heterogeneous Catalytic Studies
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Three new metal–organic porphyrinic framework compounds of zinc and 5,10,15,20-tetrakis(4-pyridyl)porphyrin (TPyP) have been synthesized under solvothermal conditions. The compounds [Zn5(C40H24N8)(C8H4O4)2(NO3)6(DMA)2] (DMA)3(H2O)8 (1; DMA=dimethylacetamide), [Zn3(C40H24N8)(C8H4O4)2(DMF)](DMF)5(H2O)12 (2), and [Zn3(C40H24N8)(C12H6O4)2(DMA)2](H2O)7 (3) have two (1) and three dimensionally (2 and 3) extended structures. All the three structures contain porphyrinic units connected through the carboxylate linkers. The nitrates bind the metal centers and are not hydrogen bonded. The different binding modes of nitrate in the structure of 1 are observed for the first time in a porphyrin-based MOF. The openness of the structure allowed us to explore metal exchange through a room-temperature metathetic route. Compound 2 undergoes 100 % exchange with copper, whereas compound 3 exchanges 70 % with copper. The copper-exchanged compounds Cu∈2 and Cu∈3 were observed to be good heterogeneous catalysts for many important organic reactions. The chemo and regioselective enamination of β-ketoesters, preparation of propargylamine derivatives as well as regioselective cycloadditions of alkyne and azide (click reactions) have been carried out with good yields and selectivity. All the compounds have been characterized by PXRD, IR, UV/Vis, atomic absorption spectroscopy (AAS), and energy-dispersive X-ray spectroscopy (for Cu exchange).
- Dutta, Gargi,Jana, Ajay Kumar,Natarajan, Srinivasan
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supporting information
p. 8932 - 8940
(2017/07/11)
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- Magnetically recoverable graphene-based nanocomposite material as an efficient catalyst for the synthesis of propargylamines: Via A3 coupling reaction
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The magnetically separable Au NPs-Fe3O4-rGO catalyst provides a robust and efficient route for the A3 coupling reaction of secondary amines, terminal alkynes and aldehyde with tolerance of diverse functional groups for the
- Hussain, Najrul,Das, Manash R.
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p. 12756 - 12766
(2017/11/06)
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- A novel tetramer copper(I) complex containing diallylphosphine ligands: Synthesis, characterization and catalytic application in A3-coupling (Aldehyde-Amine-Alkyne) reactions
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A novel tetrameric copper(I) complex containing tert-butyldiallylphosphine ligands, [CuCl{tBu-P(CH2CH = CH2)2}]4 (2), has been synthesized and characterized by structural and spectroscopic methods. X-ray diffraction analysis showed that 2 has a cubane-like solid structure of formula [CuCl{κ1(P)-tBu-P(CH2CH = CH2)2}]4. In solution, a dynamic behavior generated by the cubane ? chair isomerization was detected by variable temperature NMR analysis. DFT calculations have been performed to explain the observed dynamic equilibrium in solution. The use of copper(I) complex 2 as catalyst for the synthesis of propargylamines via A3-coupling reactions has been tested. Complex 2 is capable of promoting A3-coupling reactions of both aromatic and aliphatic aldehydes with cyclic secondary amines and phenylacetylene. The reaction proceeds under mild condition and absence of solvent.
- Rosales, Jennifer,Garcia, Juan M.,ávila, Edward,González, Teresa,Coll, David Santiago,Ocando-Mavárez, Edgar
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p. 155 - 162
(2017/09/02)
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- Single and double A3-coupling (aldehyde-amine-alkyne) reaction catalyzed by an air stable copper(I)-phosphole complex
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An air stable copper(I)-phosphole complex, [CuCl{2,5-bis(2-thienyl)-1-phenylphosphole}2] (1), was utilized as a catalyst in single and double A3-coupling reactions for preparing mono- and bi-propargylamines. A variety of aldehydes, a
- Cammarata, José Ricardo,Rivera, Rocío,Fuentes, Franmerly,Otero, Yomaira,Ocando-Mavárez, Edgar,Arce, Alejandro,Garcia, Juan M.
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supporting information
p. 4078 - 4081
(2017/09/27)
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