- Silver nanoparticles encapsulated by metal-organic-framework give the highest turnover frequencies of 105 h?1 for three component reaction by microwave-assisted heating
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Microwave (MW)-assisted heating, due to its unique properties has been used for synthesis of metal, oxide, zeolite, and metal-organic framework (MOF), and even to carry out organic reactions. However, less attention has been paid to integration of two or
- Li, Di,Dai, Xiaoping,Zhang, Xin,Zhuo, Hongying,Jiang, Yan,Yu, Yan-Bing,Zhang, Pengfang,Huang, Xingliang,Wang, Hai
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- New NHC- silver and gold complexes active in A3-coupling (aldehyde-alkyne-amine) reaction
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Silver and gold complexes bearing unsaturated N-heterocyclic carbene ligands, with unsymmetrical N-substituents and hydrogen or chlorine on backbone, have been synthetized and their efficiency tested in A3-coupling (aldehyde–alkyne–amine) react
- Mariconda, Annaluisa,Sirignano, Marco,Costabile, Chiara,Longo, Pasquale
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- A microwave-enhanced, solventless Mannich condensation on CuI-doped alumina
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Terminal alkynes react with secondary amines and paraformaldehyde to afford Mannich adducts in the presence of cuprous iodide on alumina under microwave irradiation and solvent free conditions.
- Kabalka,Wang,Pagni
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Read Online
- Synthesis and structural characterization of N-heterocyclic carbene silver complexes derived from N-ferrocenylmethyl-N′-(pyridylmethyl)imidazolium iodides
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A series of N-heterocyclic carbene (NHC) silver complexes derived from N-ferrocenylmethyl-N′-(pyridylmethyl)imidazolium iodides have been synthesized, which show remarkable structural diversity. Reaction of N-ferrocenylmethyl-N′-(2-pyridylmethyl)imidazoli
- Li, Qiang,Li, Xin,Yang, Jun,Song, Hai-Bin,Tang, Liang-Fu
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- Silver–N-heterocyclic carbene complexes-catalyzed multicomponent reactions: Synthesis, spectroscopic characterization, density functional theory calculations, and antibacterial study
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Nowadays, silver–N-heterocyclic carbene (silver–NHCs) complexes are widely used in medicinal chemistry due to their low toxic nature toward humans. Due to the success of silver–NHCs in medicinal applications, interest in these compounds is rapidly increas
- Mnasri, Aziza,Mejri, Amal,Al-Hazmy, Sadeq M.,Arfaoui, Youssef,?zdemir, Ismail,Gürbüz, Nevin,Hamdi, Naceur
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- Defect engineering: an effective tool for enhancing the catalytic performance of copper-MOFs for the click reaction and the A3coupling
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A series of Cu(i)-enriched metal-organic frameworks (MOF) of the type CuBTC (BTC = benzene-1,3,5-tricarboxylate) was prepared by a mixed-linker defect engineering technique, namely substituting a portion of a parent linker with truncated pyridine-3,5-dica
- Fan, Zhiying,Wang, Zheng,Cokoja, Mirza,Fischer, Roland A.
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- Dinuclear N-heterocyclic carbene silver complexes: Synthesis, luminescence and catalytic studies
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A new dibenzimidazole compound (1) and three dibenzimidazolium salts (2a-2c) were prepared. Reactions of these salts with silver(I) oxide in methanol led to dinuclear N-heterocyclic carbene silver complexes (3a-3c). All of the compounds were characterized
- Demir Atl?, Deniz,Gülle, Sibel
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Read Online
- Catalytic activity of N-heterocyclic carbene silver complexes derived from imidazole ligands
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The N-heterocyclic carbene (NHC)-silver(I) complexes, 3a–c of the type (NHC)AgCl were prepared from 1-(methyl)-3-(alkyl)-imidazolium chlorides (2a–c) by the reactions with Ag2O in dichloromethane as a solvent at room temperature. The complexes
- K?l?n?arslan, Rafet,Sad??, Naim
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Read Online
- Synthesis and Application of Silylene-Stabilized Low-Coordinate Ag(I)-Arene Cationic Complexes
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We report the first examples of N-heterocyclic silylene-stabilized monocoordinate Ag(I) cationic complexes weakly bound to the free arene rings (C6H6, C6Me6, and C7H8). Further, the application of these electrophilic Ag(I) complexes as catalysts has been investigated toward A3-coupling reactions, which afforded a series of propargylamines in good to excellent yields with low catalyst loading under a solvent-free condition (19 examples).
- Khan, Shabana,Muhammed, Shahila,Parameswaran, Pattiyil,Parvin, Nasrina,Sen, Nilanjana,Tothadi, Srinu
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supporting information
p. 1626 - 1632
(2021/06/28)
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- Synthesis, characterization and catalytic properties of cationic N-heterocyclic carbene silver complexes
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Three new dibenzimidazolium salts bridged by 2-methylenepropane-1,3-diyl group were synthesized. Their dinuclear N-heterocyclic carbene Ag(I) complexes were prepared by the reactions of these salts with Ag2O. The structures of the synthesized compounds were defined by nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FT-IR), elemental analysis, and LC-MSMS (for complexes) techniques. Stability of the silver complexes was confirmed by 1H NMR spectroscopy. Catalytic activities of Ag(I) compounds were tested for three-component coupling reaction of some aldehydes, amines, and phenylacetylene.
- Atli, Deniz Demir
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p. 577 - 584
(2021/07/26)
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- Dinuclear silver-bis(N-heterocyclic carbene) complexes: Synthesis, catalytic activity in propargylamine formation and computational studies
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Preparation of a series of 1,1′-dialkyl-3,3′-(2-methylenepropane-1,3-diyl)dibenzimidazolium salts (alkyl = ethyl, propyl, butyl) (2a-2c) and their dinuclear bis(N-heterocyclic carbene) silver complexes (3a-3c) is reported. The silver complexes were synthe
- Demir Atli, Deniz,?en, Betül
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p. 2289 - 2301
(2021/09/07)
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- NbCl5-Mg reagent system in regio-and stereoselective synthesis of (2Z)-alkenylamines and (3Z)-alkenylols from substituted 2-alkynylamines and 3-alkynylols
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The reduction of N,N-disubstituted 2-alkynylamines and substituted 3-alkynylols using the NbCl5 –Mg reagent system affords the corresponding dideuterated (2Z)-alkenylamine and (3Z)-alkenylol derivatives in high yields in a regio-and stereoselective manner through the deuterolysis (or hydrolysis). The reaction of substituted propargylamines and homopropargylic alcohols with the in situ generated low-valent niobium complex (based on the reaction of NbCl5 with magnesium metal) is an efficient tool for the synthesis of allylamines and homoallylic alcohols bearing a 1,2-disubstituted double bond. It was found that the well-known approach for the reduction of alkynes based on the use of the TaCl5-Mg reagent system does not work for 2-alkynylamines and 3-alkynylols. Thus, this article reveals a difference in the behavior of two reagent systems—NbCl5-Mg and TaCl5-Mg, in relation to oxygen-and nitrogen-containing alkynes. A regio-and stereoselective method was developed for the synthesis of nitrogen-containing E-β-chlorovinyl sulfides based on the reaction of 2-alkynylamines with three equivalents of methanesulfonyl chloride in the presence of stoichiometric amounts of niobium(V) chloride and magnesium metal in toluene.
- Dzhemilev, Usein M.,Gabdullin, Azat M.,Kadikova, Rita N.,Mozgovoj, Oleg S.,Ramazanov, Ilfir R.
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- Decavanadate-based Transition Metal Hybrids as Bifunctional Catalysts for Sulfide Oxidation and C—C Bond Construction
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The development of bifunctional catalysts has drawn much attention in realizing efficient and feasible catalytic systems to meet the diverse demand of potential industrial applications. Design of stable and powerful bifunctional catalysts for various cata
- Chen, Yifa,Duan, Wenzeng,Gong, Shuwen,Gu, Xiaoyu,Huang, Xianqiang,Qi, Yuquan,Shen, Guodong,Xue, Zechun,Yang, Bingchuan,Zhang, Yanru
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p. 2495 - 2503
(2021/07/31)
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- A green approach for A3-coupling reactions: an experimental and theoretical study on NHC silver and gold catalysts
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The synthesis of propargylamines by traditional methods is limited by several drawbacks such as anhydrous conditions, low temperatures and by-products. A3-coupling reactions (aldehydes, amines, and alkynes), that involve a catalytic amount of m
- Costabile, Chiara,Crispini, Alessandra,Longo, Pasquale,Mariconda, Annaluisa,Scarpelli, Francesca,Sirignano, Marco
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p. 18509 - 18517
(2021/10/19)
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- Self-assembly of three Ag-polyoxovanadates frameworks for their efficient construction of C–N bond and detoxification of simulant sulfur mustard
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Three imidazole-modified Ag-polyoxovanadates frameworks (APFs) with a controllable molar ratio of Ag+ to polyoxovanadates (POVs) [Ag(IM)2]2V4O12?2Ag(IM)2 (APF-1), [Ag2(1-eIM)sub
- Cui, Yanan,Huang, Xianqiang,Li, Jikun,Shen, Guodong,Xue, Zechun,Yang, Guoping,Yao, Qingxia,Zhang, Yalin,Zhou, Jinhong
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supporting information
(2021/11/18)
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- Synthesis and characterization of magnetic glycocyamine-modified chitosan as a biosupport for the copper immobilization and its catalytic activity investigation
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Trichloro-1,3,5-triazine agent was used for chitosan functionalization and as a bridge between the functionalized chitosan and glycocyamine to form a bio ligand for the copper coordination. The magnetization of modified chitosan was done using of Fe3
- Rafiee,Karder, F. Rezaie
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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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- 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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- Reduced graphene oxide-immobilized iron nanoparticles Fe(0)@rGO as heterogeneous catalyst for one-pot synthesis of series of propargylamines
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Abstract: Iron nanoparticles immobilized on reduced graphene oxide (rGO), nanocomposite Fe(0)@rGO 1, were prepared in situ by reduction of GO and FeCl3·6H2O using sodium borohydride under nitrogen atmosphere. The nanocomposite 1 was
- Kujur, Shelly,Pathak, Devendra Deo
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p. 369 - 384
(2019/08/28)
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- Two inorganic-organic hybrid silver-polyoxometalates as reusable catalysts for one-pot synthesis of propargylamines: Via a three-component coupling reaction at room temperature
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By the combination of Ag-complexes and Keggin POMs, two novel inorganic-organic silver-polyoxometalates hybrids, [Ag3L2(DMSO)2][PW12O40]·4DMSO (1) and [(Ag2L2)2][SiWs
- Dou, Ming-Yu,Huang, Xian-Qiang,Yang, Guo-Yu
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p. 2642 - 2648
(2020/04/24)
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- Copper-Catalyzed Tandem Sulfuration/Annulation of Propargylamines with Sulfur via C-N Bond Cleavage
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Copper-catalyzed aerobic oxidative sulfuration and annulation of propargylamines with elemental sulfur is described. The tandem reaction involves C-N bond cleavage and the formation of multiple C-S bonds, affording 1,2-dithiole-3-thiones in good to excellent yields with good functional group tolerance.
- Xu, Hong-Hui,Zhang, Xiao-Hong,Zhang, Xing-Guo
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p. 7894 - 7900
(2019/06/27)
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- Heterogeneous bimetallic Au–Co nanoparticles as new efficient catalysts for the three-component coupling reactions of amines, alkynes and CH2Cl2
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Abstract: Propargylamines are key intermediates for the synthesis of many biologically active molecules. A new synthesis of propargylamines via a three component-coupling reactions of amines, alkynes and dichloromethane (AHA) using bimetallic nanoparticle
- Berrichi,Bachir,Bedrane,Choukchou-Braham,Belkacemi
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p. 3481 - 3495
(2019/09/03)
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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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- Practical synthesis of silyl-protected and functionalized propargylamines using nanostructured Ag/TiO2 and Pt/TiO2 as active recyclable catalysts
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Abstract: Herein we report the use of Ag/TiO2 and Pt/TiO2 nanocatalysts to promote the synthesis of a series of silyl-protected and functionalized propargylamine derivatives through alkyne–amine–aldehyde (A3) coupling unde
- Mohamed, Yasser M. A.,El Nazer, Hossam A.,Solum, Eirik Johansson
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p. 435 - 445
(2019/02/12)
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- Preparation method and uses of 4,6-bis(pyridine-2-yl)pyrimidine-2-amine copper coordination compound
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The invention discloses a 4,6-bis(pyridine-2-yl)pyrimidine-2-amine copper coordination compound preparation method, which comprises: placing copper chloride, 4,6-di(pyridine-2-yl)pyrimidine-2-amine and dimethyl sulfoxide in a beaker, carrying out a reacti
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Paragraph 0044-0046
(2019/11/04)
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- Recyclable Cu/C3N4 composite catalyzed AHA/A3 coupling reactions for the synthesis of propargylamines
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The heterogeneous Cu/C3N4 catalyst was found to be efficient for the synthesis of propargylamines using a three-component coupling reaction of alkynes, CH2Cl2 and amines (AHA) without additional base. Moreover,
- Xu, Hang,Wang, Jun,Wang, Peng,Niu, Xiyu,Luo, Yidan,Zhu, Li,Yao, Xiaoquan
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p. 32942 - 32947
(2018/10/15)
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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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- 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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supporting information
(2017/12/18)
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- Construction of polymeric Cu(I) N-heterocyclic carbene complex utilizing terpyridine-Fe(II) as linkers: formation of an efficient and recyclable catalyst
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A metal-coordination-driven self-assembly using the predesigned building block has been developed. Herein, the catalytic active NHC–Cu(I) units were introduced into the terpyridine metal coordination polymers. The self-assembled architecture, as a heterog
- Yang, Jin
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p. 155 - 163
(2018/02/09)
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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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- Ultrasonic and bio-assisted synthesis of Ag@HNTs-T as a novel heterogeneous catalyst for the green synthesis of propargylamines: A combination of experimental and computational study
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A novel heterogeneous catalyst is prepared through functionalization of halloysite nanotube with 1H-1,2,3-triazole-5-methanol and subsequent immobilization of silver nanoparticles through bio-assisted approach using Arctiumplatylepis extract. The resulting catalyst, Ag@HNTs-T, was characterized by using SEM/EDX, BET, XRD, FTIR, ICP-AES, TGA, DTGA and elemental mapping analysis. Moreover, we computationally assessed metal-ligand interactions in Ag@HNTs-T complex model to interpret the immobilization behavior of silver nanoparticles on HNTs surface via quantum chemistry computations. The catalytic activity of the catalyst was studied for the synthesis of propargylamines via A3 and KA2 coupling reactions under ultrasonic irradiation. The results demonstrated that Ag@HNTs-T could efficiently promote these reactions to furnish the corresponding products in high yields and short reaction times. The study of the recyclability of the catalyst and Ag(0) leaching confirmed that the catalyst was recyclability up to four reaction runs with slight Ag(0) leaching.
- Malmir, Masoumeh,Heravi, Majid M.,Sadjadi, Samahe,Hosseinnejad, Tayebeh
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- Post-synthetically modified MOF for the A3-coupling reaction of aldehyde, amine, and alkyne
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A new heterogeneous NHC catalyst (Ag-NHC-MOF) was synthesized by the post-synthetic modification of an azolium-containing metal-organic framework. The structure of the catalyst was well defined and fully characterized using various techniques such as PXRD, FE-SEM, HR-TEM, XPS, FT-IR, TGA, BET, 1H-NMR, 13C-NMR, EDS, and ICP. The catalyst showed an excellent activity towards the A3-coupling reaction with a broad substrate scope. The A3-coupling reaction was performed under ambient conditions and full conversion was reached within just 1 hour for the model reaction. The heterogeneous silver NHC MOF (Ag-NHC-MOF) catalyst can be recycled and reused at least four times without a significant loss of activity. In comparison with previously reported heterogeneous catalysts applied for the A3-coupling reaction, the Ag-NHC-MOF demonstrates a superior performance for the A3-coupling reaction.
- Kassymova, Meruyert,De Mahieu, Alaric,Chaemchuen, Somboon,Demeyere, Patrick,Mousavi, Bibimaryam,Zhuiykov, Serge,Yusubov, Mekhman S.,Verpoort, Francis
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p. 4129 - 4140
(2018/08/24)
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- [Zn(l-proline)2] Catalyzed One-Pot Synthesis of Propargylamines Under Solvent-Free Conditions
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A simple, one-pot, three-component, green synthesis of a wide range of propargylamines is reported by A3-coupling (aldehyde, alkyne and amine) via C–H activation of alkynes using [Zn(l-proline)2] as an efficient and reusable heteroge
- Layek, Samaresh,Agrahari, Bhumika,Kumari, Shweta,Anuradha,Pathak, Devendra D.
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p. 2675 - 2682
(2018/06/20)
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- A facile synthesis methodology for preparation of Ag-Ni-reduced graphene oxide: a magnetically separable versatile nanocatalyst for multiple organic reactions and density functional study of its electronic structures
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Here, we report a simple ‘in situ' co-precipitation reduction synthesis method for the preparation of nanocatalysts composed of Ag, Ni nanoparticles, and reduced graphene oxide (RGO). First-principles calculations based on Density Functional Theory (DFT) were performed to obtain the electronic structures and properties of Ag-Ni-graphene superlattice and to understand the interfacial interactions which exist at the interface between Ag, Ni, and graphene. The catalytic performance of the synthesized catalysts (AgxNi(1?x))yRGO(100?y) were evaluated for four reactions (i) reduction of 4-nitrophenol (4-NP) in the presence of excess NaBH4 in aqueous medium, (ii) A3 coupling reaction for the synthesis of propargylamines, (iii) epoxidation of styrene, and (iv) ‘Click reaction' for the synthesis of 1,2,3-triazole derivatives. For all of these reactions the catalyst composed of Ag, Ni, and RGO, exhibited significantly higher catalytic activity than that of pure Ag, Ni, and RGO. Moreover, an easy magnetic recovery of this catalyst from the reaction mixture after completion of the catalytic reactions and the good reusability of the recovered catalyst is also reported here. To the best of our knowledge, this is the first time the demonstration of the versatile catalytic activity of (AgxNi(1?x))yRGO(100?y) towards multiple reactions, and the DFT study of its electronic structure have been reported.
- Chandel, Madhurya,Makkar, Priyanka,Ghosh, Barun Kumar,Moitra, Debabrata,Ghosh, Narendra Nath
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p. 37774 - 37788
(2018/11/26)
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- Naked Au nanoparticles monodispersed onto multifunctional cellulose nanocrystal-graphene hybrid sheets: Towards efficient and sustainable heterogeneous catalysts
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A simple, clean, and efficient synthesis method has been developed for deposition of ~3 nm monodisperse "naked" gold nanoparticles (Au NPs) onto cellulose nanocrystal-graphene (CNC-G) hybrid sheets without the use of additional reducing and capping agents. The as-prepared catalysts (Au@CNC-G) were examined using FT-IR spectroscopy, thermogravimetric analysis (TGA), atomic force microscopy, electron microscopy, wide-angle X-ray diffraction, and X-ray photoelectron spectroscopy (XPS). After some optimization, the Au@CNC-G catalyst exhibited robust catalytic activity, impressive stability, and good flexibility for the "one-pot" reaction of an alkyne, an amine, and an aldehyde (A3-coupling) in water. The catalytic activity of the Au@CNC-G catalyst could be attributed to the synergistic effect derived from the coexistence of CNC and graphene. The Au3+ ions could be in situ reduced to create fine Au NPs and simultaneously anchored on the surface of CNC-G hybrid sheets through coordination, leading to the uniform dispersion of the Au NPs. Moreover, the Au@CNC-G catalyst could be conveniently recycled and reused many times, thus lowering the cost and minimizing the environmental pollution caused by organic solvents and heavy metal ions.
- Wang, Yameng,Zhang, Huinian,Lin, Xiangjun,Chen, Shuai,Jiang, Zhongjie,Wang, Junzhong,Huang, Jianlin,Zhang, Fang,Li, Hexing
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p. 2197 - 2203
(2018/02/07)
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- Magnetically recoverable Fe3O4@Au-coated nanoscale catalysts for the A3-coupling reaction
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The utility of novel Fe3O4@Au nanoparticles as magnetically separable and recyclable heterogeneous catalysts for the A3-coupling reaction of aldehydes, amines and terminal alkynes to yield the corresponding propargylamines
- Munshi, Alaa M.,Shi, Mingwen,Thomas, Sajesh P.,Saunders, Martin,Spackman, Mark A.,Iyer, K. Swaminathan,Smith, Nicole M.
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p. 5133 - 5137
(2017/04/27)
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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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- Cu (I)-based metal organic coordination polymer and preparation method and application thereof
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The invention discloses organic ligand L for synthesizing Cu (I)-based metal organic coordination polymer, and Cu (I)-based metal organic coordination polymers Cu-CPs; the meal organic coordination polymers Cu-CPs are synthesized through the organic ligand L and are of 1D single-stranded structure, having two crystallographically independent Cu metal centers, with one center positioned on 1D strand and connecting imidazole N atoms on two ligands, and with the other positioned outside the 1D strand and having two Br ligands present in the form of [CuBr2]-. There is weak M-M action between the two Cu metal centers. The Cu-CPs are efficient in catalyzing phenylethylene oxide ring-opening reaction, p-bromophenol acetylization and Mannich reaction with no need for heavy metals to engage in catalyst reaction, environmental damage due to heavy metals is reduced, reaction temperature is medium, reaction time is short, little catalyst is used, no other additives are used, and compared with free heavy metal salts, the polymers are available for more than 5 times of reuse.
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Paragraph 0053; 0056; 0094; 0095; 0110; 0125
(2017/08/27)
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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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- 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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- Cu@furfural imine-decorated halloysite as an efficient heterogeneous catalyst for promoting ultrasonic-assisted A3 and KA2 coupling reactions: A combination of experimental and computational study
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Halloysite nanoclays (HNTs) were functionalized with (3-chloropropyl) trimethoxysilan and subsequently reacted with thiosemicarbazide and furfural to furnish furfural imine functionalized HNTs, which could serve as an efficient support for immobilization
- Sadjadi, Samahe,Hosseinnejad, Tayebeh,Malmir, Masoumeh,Heravi, Majid M.
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p. 13935 - 13951
(2017/11/27)
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- Based on double-pyrazole methyl phenoxy methyl imidazole nitrogen heterocyclic cabeen silver complex and its preparation method and application
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The invention relates to a nitrogen heterocyclic carbene silver complex based on bispyrazole methyl phenoxy methylimidazole and a preparation method and application thereof. The preparation method of the nitrogen heterocyclic carbene silver complex is as follows: at room temperature in dark conditions, a bispyrazole methyl phenoxy methyl substituted imidazolium salt and silver oxide in the molar ratio of 1 to 0.7 are dissolved in an organic solvent for reaction for 24 hours, then filtered and concentrated to prepare the nitrogen heterocyclic carbene silver complex. The nitrogen heterocyclic carbene silver complex has strong capability of emission fluorescence and catalyzing of coupled reaction of acetylene, amine and aldehyde three components, and can be mainly used in fluorescent materials and organic catalysis technology field.
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Paragraph 0031-0033
(2017/01/17)
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- A Versatile CuII Metal-Organic Framework Exhibiting High Gas Storage Capacity with Selectivity for CO2: Conversion of CO2 to Cyclic Carbonate and Other Catalytic Abilities
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A linear tetracarboxylic acid ligand, H4L, with a pendent amine moiety solvothermally forms two isostructural metal-organic frameworks (MOFs) LM (M=ZnII, CuII). Framework LCu can also be obtained from
- De, Dinesh,Pal, Tapan K.,Neogi, Subhadip,Senthilkumar,Das, Debasree,Gupta, Sayam Sen,Bharadwaj, Parimal K.
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p. 3387 - 3396
(2016/03/05)
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- Synthesis, structure and multifunctional catalytic properties of a Cu(i)-coordination polymer with outer-hanging CuBr2
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A 1D Cu(i)-coordination polymer [(CuL1)(CuBr2), 1] carrying external copper bromide moieties was synthesized. The outer-hanging [CuBr2]- moiety is attached to the 1D Cu(i)-CP backbone via a Cu?Cu bonding interaction, which makes it look like a coordination polymer supported CuBr2 species. 1 exhibits excellent multifunctional catalytic activity for phenol acetylation, A3-coupling (aldehyde-alkyne-amine) and styrene oxide methanolysis reactions. Its heterogeneous catalytic nature was confirmed by solution leaching experiment and it can be reused without significant loss of its catalytic activity and selectivity for the above reactions.
- Zhu, Neng-Xiu,Zhao, Chao-Wei,Yang, Jing,Wang, Xue-Ru,Ma, Jian-Ping,Dong, Yu-Bin
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p. 108645 - 108653
(2016/11/30)
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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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p. 1128 - 1138
(2016/06/01)
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- Zn(OTf)2-Mediated Expeditious and Solvent-Free Synthesis of Propargylamines via C-H Activation of Phenylacetylene
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Zn(OTf)2-mediated expeditious and solvent-free synthesis of propargylamines via A3 coupling of aldehydes, amines, and phenylacetylene has been described. The described protocol proceeds effectively with variety of substituted benzaldehydes, enolizable aldehyde, and formaldehyde. Recyclability of the catalyst, low catalyst loading, and use of inexpensive catalyst are the key features of the present protocol.
- Sarode, Prashant B.,Bahekar, Sandeep P.,Chandak, Hemant S.
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supporting information
p. 2209 - 2212
(2016/10/12)
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- Nano-Fe3O4@TiO2/Cu2O Core-shell Composite: A Convenient Magnetic Separable Catalyst for A3 and KA2 Coupling
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An eco-efficient one-pot three component reaction between different aldehydes or ketones with alkynes and amines for the synthesis of propargylamines was performed using Fe3O4@TiO2/Cu2O as a nano-magnetic composite under solvent free condition. The catalyst showed remarkable catalytic activity by decreasing the time of the reaction in comparison of other reported magnetic catalysts. In addition, the Fe3O4@TiO2/Cu2O can be easily recycled and reutilized for five times without apparent loss of catalytic activity.
- Elhampour, Ali,Nemati, Firouzeh
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p. 653 - 659
(2016/09/03)
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- Ag-doped nano magnetic γ-Fe2O3@DA core-shell hollow spheres: An efficient and recoverable heterogeneous catalyst for A3 and KA2 coupling reactions and [3 + 2] cycloaddition
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An effective protocol for the fabrication of Ag-doped nano magnetic γ-Fe2O3@DA core-shell hollow spheres (h-Fe2O3@DA/Ag) by a simple hydrothermal method is demonstrated without any templates in the reaction system. The synthesized core-shell structure was successfully characterized in terms of the chemical composition, surface morphology, and magnetic properties using FT-IR, VSM, TGA, TEM, FE-SEM, EDS, and XRD patterns. The possible formation mechanism of this magnetic γ-Fe2O3@DA/Ag hollow sphere structure is described based on the experimental results. In addition, as a physical property, the apparent shell density was determined using the specific surface area (BET) and shell thickness (BJH). The important, novel and unique catalyst with a hollow structural character and strong magnetic behavior exhibited a high catalytic activity in the A3 and KA2 coupling reactions and [3 + 2] cycloaddition for the synthesis of 1H-tetrazoles. Furthermore, the recovered catalyst of the reaction mixture was facilitated by a magnetic field and multiple recycling was carried out without any significant loss in the catalytic activity.
- Elhampour,Malmir,Kowsari,Boorboor Ajdari,Nemati
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p. 96623 - 96634
(2016/10/25)
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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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p. 300 - 306
(2016/10/04)
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- Ag(I) complexes of benzimidazol-2-ylidene ligands: A study of catalytic efficiency towards three-component coupling reactions
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The N -heterocyclic carbene (NHC)-Ag(I) complexes 3a-c were synthesized from benzimidazolium chlorides (2a-c = NHC.HCl), incorporating benzyl derivatives and a 2-methoxyethyl group (a: 3N = 2,4,6-trimethylbenzyl; b: 3N = 2,3,5,6-tetr
- Kilin?arslan, Rafet,Sadi?, Naim,?etinkaya, Bekir
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p. 681 - 687
(2016/07/06)
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- Aggregates of perylene bisimide stabilized superparamagnetic Fe3O4 nanoparticles: an efficient catalyst for the preparation of propargylamines and quinolines via C-H activation
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Aggregates of the perylene bisimide derivative 3 act as reactors and stabilizers for the preparation of superparamagnetic Fe3O4 nanoparticles (NPs) which exhibit excellent catalytic efficiency in (i) A3-coupling and aldehyde free coupling reactions for the preparation of propargylamines and (ii) tandem intramolecular cyclization reaction for the synthesis of quinolines via C-H activation.
- Kaur, Sandeep,Kumar, Manoj,Bhalla, Vandana
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supporting information
p. 16327 - 16330
(2015/11/16)
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- Continuous flow reactions in water for the synthesis of propargylamines via a metal-free decarboxylative coupling reaction
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Abstract A range of propargylamines was synthesized via the metal-free decarboxylative coupling of alkynyl carboxylic acids with amines and paraformaldehyde in water, using a continuous flow reaction system. Aryl- and alkyl-substituted propiolic acids were found to react with secondary amines in the presence of paraformaldehyde, at 140°C in water to give the desired propargylamines in good yield.
- Jung, Bongkyun,Park, Kyungho,Song, Kwang Ho,Lee, Sunwoo
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p. 4697 - 4700
(2015/07/28)
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