- Rh(I)-catalyzed CO gas-free cyclohydrocarbonylation of alkynes with formaldehyde to α,β-butenolides
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The rhodium(I)-catalyzed reaction of alkynes with formaldehyde proceeds via the double incorporation of a carbonyl moiety from formaldehyde, resulting in a CO gas-free cyclohydrocarbonylation leading to α,β-butenolides. The Royal Society of Chemistry 2005.
- Fuji, Koji,Morimoto, Tsumoru,Tsutsumi, Ken,Kakiuchi, Kiyomi
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- Microwave-assisted copper(I) catalyzed A3-coupling reaction: Reactivity, substrate scope and the structural characterization of two coupling products
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The application of highly efficient catalyst [{Cu(μ ? I)2Cu}(PPh3)4] for the synthesis of biologically and pharmaceutically important propargylamine derivatives through microwave assisted A3-coupling reaction is
- Kashid, Vitthalrao S.,Balakrishna, Maravanji S.
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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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- 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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- Synthesis of 2,3-acetylenic amines by aminomethylation of acetylenes with geminal diamines
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A general and effective procedure has been developed for the synthesis of symmetrical and unsym- metrical 2,3-acetylenic amines by aminomethylation of terminal mono- and diacetylenes with geminal diamines in the presence of transition metal salts and complexes.
- Shaibakova,Titova,Makhmudiyarov,Ibragimov,Dzhemilev
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- Copper(II) carboxymethylcellulose (CMC-CuII) as an efficient catalyst for aldehyde-alkyne-amine coupling under solvent-free conditions
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A novel and eco-friendly three-component reaction of aldehydes, amines, and alkynes (A3 coupling) catalyzed by a recoverable copper(ii) carboxymethylcellulose (CMC-CuII) catalyst has been developed, producing a diverse range of propargylamines under solvent-free conditions in good yields. The CMC-CuII catalyzed reaction is especially effective for reactions involving aromatic and aliphatic aldehydes. High catalytic activity was obtained in the presence of 5 mol% CMC-CuII without any other co-catalyst, additives, or bases under aerobic conditions. Moreover, the catalyst can be easily recovered and reused for at least four cycles without significant decrease in its catalytic activity.
- Liu, Xiaoping,Lin, Bijin,Zhang, Zhuan,Lei, Hao,Li, Yiqun
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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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- Stable mesoporous Fe/TiO2 nanoparticles: A recoverable catalyst for solvent-free synthesis of propargylamine via C[sbnd]H activation
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Fe-doped mesoporous metal oxides (Fe/MO2, M = Si and Ti) were synthesized with particle size in the range of 10–15 nm via modified sol–gel method. The Fe modified SiO2 and TiO2 have proved to be very efficient catalysts in three-component coupling of aldehydes, alkynes and amines for the solvent-free synthesis of proargylamines. Among the two Fe-doped metal oxide catalysts, Fe/TiO2 gives 94% propargylamine yield at 245 W microwave power for few minutes under solvent free condition and found to be a better catalyst. With a Fe/TiO2 heterogeneous catalyst and in the absence of solvent, the proposed process for propargylamine synthesis is green and environmentally benign protocol.
- Kotadia, Deepali A.,Soni, Saurabh S.
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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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- Nano copper(I) oxide-zinc oxide catalyzed coupling of aldehydes or ketones, secondary amines, and terminal alkynes in solvent-free conditions
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A simple, efficient, and environmentally benign method has been described for the synthesis of propargylamines through a one-pot three-component coupling reaction of terminal alkynes, aldehydes or ketones, and secondary amines in excellent isolated yields, under solvent-free conditions, using a catalytic amount of nano Cu2O-ZnO as the recyclable, and heterogeneous catalyst. The catalyst can be reused in further catalytic reactions, and it was found that its activity remained largely unchanged for ten successive runs. The catalyst was characterized by using powder X-ray diffraction (XRD), a transmission electron microscopy (TEM), a scanning electron microscopy (SEM), BET surface area measurement and FT-IR spectroscopy.
- Hosseini-Sarvari, Mona,Moeini, Fatemeh
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- Self-Assembled Cyclophane-Type Copper(I) Complexes of 2,4,6-Tris(diphenylphosphino)-1,3,5-triazine and Their Catalytic Application
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The triazine-based trisphosphine, 2,4,6-tris(diphenylphosphino)-1,3,5-triazine (1) was prepared in improved yield by reacting cyanuric chloride with 3 equiv of trimethylsilyldiphenylphosphine. The solid-state structure of 1 showed short intermolecular P··
- Ananthnag, Guddekoppa S.,Mague, Joel T.,Balakrishna, Maravanji S.
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- Mechanochemical Nucleophilic Substitution of Alcohols via Isouronium Intermediates**
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An expansion of the solvent-free synthetic toolbox is essential for advances in the sustainable chemical industry. Mechanochemical reactions offer a superior safety profile and reduced amount of waste compared to conventional solvent-based synthesis. Here
- Dalidovich, Tatsiana,Nallaparaju, Jagadeesh Varma,Shalima, Tatsiana,Aav, Riina,Kananovich, Dzmitry G.
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- Nano and Sub-nano Gold–Cobalt Particles as Effective Catalysts in the Synthesis of Propargylamines via AHA Coupling
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Abstract: Titania supported Au–Co catalysts with nano- and sub-nanoparticles, were prepared with 1% Au and different contents of cobalt by one pot deposition precipitation with urea. Monometallic gold and cobalt catalysts were also prepared by the same me
- Bensaad, Meriem,Berrichi, Amina,Bachir, Redouane,Bedrane, Sumeya
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p. 1068 - 1079
(2020/09/11)
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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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- 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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- 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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- 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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- Glyoxylic Acid: A Carboxyl Group-Assisted Metal-Free Decarboxylative Reaction Toward Propargylamines
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Readily available propargylamines are not only fundamental building blocks in organic synthesis, but also possess many prominent biological activities. A highly efficient, concise and environmentally benign decarboxylative reaction of glyoxylic acid monohydrate with secondary amines and alkynes has been elaborated, and a variety of propargylamines are delivered in moderate to good yields under metal-free conditions. A mechanism involving a carboxyl group that assists the reactivity of alkynes, which makes the procedure of Michael addition proceeded smoothly, has been proposed.
- Huang, Liliang,Xie, Yujuan,Ge, Panyuan,Huang, Junhai,Feng, Huangdi
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supporting information
p. 2448 - 2451
(2021/06/28)
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- Gram-Scale Synthesis of Cu(II)@COF via Solid-State Coordination Approach for Catalysis of Alkyne-Dihalomethane-Amine Coupling
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A novel covalent organic framework material COF-DM, which contains chelating coordination environments, was synthesized at the gram level under mild conditions. In addition, its Cu(II)-loaded complex of Cu(II)@COF-DM was prepared by impregnating COF-DM in
- Kan, Xuan,Wang, Jian-Cheng,Kan, Jing-Lan,Shang, Jin-Yan,Qiao, Hua,Dong, Yu-Bin
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p. 3393 - 3400
(2021/03/08)
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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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- 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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- Easy Access to 2,4-Disubstituted Cyclopentenones by a Gold(III)-Catalyzed A3-Coupling/Cyclization Cascade
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An efficient and convenient synthesis of 2,4-disubstituted cyclopentenones has been achieved through a Au(III)-catalyzed isomerization-A3-coupling/cyclization cascade. A possible mechanism involving an initial Au(III)-catalyzed isomerization, A3-type coupling, and cyclization via an enol intermediate is postulated.
- Hu, Xiwen,Li, Jian,Liu, Li,Xu, Yue,Zhu, Shangrong
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supporting information
p. 9478 - 9483
(2020/12/21)
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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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- 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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- 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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- 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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- 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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- Construction of four copper coordination polymers derived from a tetra-pyridyl-functionalized Calix[4]arene: Synthesis, structural diversity, and catalytic applications in the A3 (Aldehyde, Alkyne, and Amine) coupling reaction
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Solvothermal reactions of CuX2 (X = NO3, Cl, Br, I) with tetra-pyridyl-functionalized calix[4]arene at 130 °C afforded four novel coordination polymers, {[(CuNO3)2L]·MeOH}n (1), [(CuCl2)-L0.5]n (2), [(Cu3Br3)L]n (3), and [(Cu3I3)L]n (4), where L = 25,26,27,28-tetra[(3-pyridylmethyl)oxy]calix[4]arene. All the products were characterized by infrared spectroscopy, thermogravimetric analysis, single-crystal X-ray diffraction, and powder X-ray diffraction. Crystal structure analysis reveals that 1 holds a one-dimensional (1D) double-chain constructed by mononuclear [Cu(NO3)] units and L linkers, while 2 features a 1D chain and its bowl-shaped L ligands work as linkers to connect the dinuclear [Cu2Cl4] units. Compounds 3 and 4 bear similar two-dimensional networks, in which each trinuclear [Cu3Br3]/[Cu3I3] unit works as a three-connecting node to connect its six equivalents by sharing L ligands. These results demonstrate that different anions have a significant effect on the final structure formation. Compounds 1?4 were employed as catalysts for the A3 coupling reaction under microwave irradiation. Notably, 3 showed the best catalytic properties for the synthesis of versatile propargylamines (yield up to 94% in only 10 min) from the A3 reaction of formaldehyde with a variety of alkynes and amines.
- Yu, Cai-Xia,Hu, Fei-Long,Liu, Meng-Yu,Zhang, Cai-Wen,Lv, Yun-He,Mao, Shu-Kuan,Liu, Lei-Lei
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p. 5441 - 5448
(2018/03/02)
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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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- 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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- 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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- 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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- 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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- Cu2O/nano-CuFe2O4: A novel and recyclable magnetic catalyst for three-component coupling of carbonyl compounds-alkynes-amines under solvent-free condition
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Cu2O/nano-CuFe2O4 magnetic composite with different loadings of Cu2O has been synthesized by feasible and low-cost method. The as-prepared composite was fully characterized by FT-IR, XRD, FEG-SEM, EDS and VSM analyzer. The catalytic activity of magnetic composite for synthesis of propargylamines was evaluated. The catalyst has many obvious advantages and easily separated via an external magnet. It can be reused for five successive runs.
- Nemati, Firouzeh,Elhampour, Ali,Farrokhi, Hadi,Bagheri Natanzi, Mahshid
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- Highly efficient and scale-up synthesis of propargylamines catalyzed by graphene oxide-supported CuCl2 catalyst under microwave condition
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An efficient, green and practical approach was developed to synthesize propargylamines using recyclable GO-CuCl2 via a one-pot multicomponent aldehyde-alkyne-amine (A3) coupling reaction. The propargylamines are readily obtained in g
- Xiong, Xingquan,Chen, Huixin,Zhu, Rongjun
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- Methods for Preparating Propargylamines through Metal-Free Decarboxylative Three-Component Coupling Reaction
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The present invention relates to a method for producing propargylamine or derivatives thereof through a decarboxylative reaction without using a metal catalyst by making alkynyl carboxylic acid, aldehyde and amine react. According to the method of the pre
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Paragraph 0126-0129; 0132-0134
(2016/10/09)
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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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- Supported nano gold catalyzed three-component coupling reactions of amines, dichloromethane and terminal alkynes (AHA)
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A simple and efficient method for the synthesis of pharmaceutically relevant propargylamines through one-pot three-component coupling reactions of amines, CH2Cl2, and terminal alkynes (AHA) using nano Au/CeO2 as a heteroge
- Berrichi, Amina,Bachir, Redouane,Benabdallah, Mohamed,Choukchou-Braham, Noureddine
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p. 1302 - 1306
(2015/03/04)
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- Oyster shell waste supported CuCl2 for aldehyde-alkyne-amine coupling reaction to propargylamines
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The development of an economic and simple heterogeneous oyster shell waste supported CuCl2 catalyst for the aldehyde-alkyne-amine (A3) coupling reaction was reported. The waste oyster shell powder (OSP) supported CuCl2 (OSP-CuCl
- Xiong, Xingquan,Chen, Huixin,Zhu, Rongjun
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p. 2006 - 2013
(2015/09/28)
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- One-pot multi-component route to propargylamines using zinc oxide under solvent-free conditions
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In this paper, commercially available ZnO was found to be a highly effective catalyst for three-component coupling reactions of alkynes, aldehydes/or ketone and amines (A3-coupling) via C-H activation. The reactions could be applied to both aromatic and aliphatic aldehydes. Nearly quantitative yields of the desired products were obtained in most cases. No co-catalyst or activator is required, and water is the only by-product in the reactions. Heterogeneous nature of the catalyst made it reusable for further chemical reactions.
- Hosseini-Sarvari, Mona,Moeini, Fatemeh
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p. 439 - 449
(2014/07/21)
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- Highly efficient and scale-up synthesis of propargylamines catalyzed by graphene oxide-supported CuCl2 catalyst under microwave condition
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An efficient, green and practical approach was developed to synthesize propargylamines using recyclable GO-CuCl2 via a one-pot multicomponent aldehyde-alkyne-amine (A3) coupling reaction. The propargylamines are readily obtained in g
- Xiong, Xingquan,Chen, Huixin,Zhu, Rongjun
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- Efficient synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines over silver catalysts
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A simple, efficient and highly functional group compatible method for the synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines using silver catalysts has been developed.
- Chen, Xiuling,Chen, Tieqiao,Zhou, Yongbo,Au, Chak-Tong,Han, Li-Biao,Yin, Shuang-Feng
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supporting information
p. 247 - 250
(2014/01/06)
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- Silica nanospheres supported diazafluorene iron complex: An efficient and versatile nanocatalyst for the synthesis of propargylamines from terminal alkynes, dihalomethane and amines
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We present the synthesis of an efficient heterogeneous silica nanosphere supported iron catalyst (SiO2@APTES@DAFO-Fe) and its catalytic application in a one pot three-component coupling reaction of terminal alkynes, dihalomethane and secondary
- Sharma,Sharma, Shivani,Gaba, Garima
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p. 49198 - 49211
(2014/12/11)
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- Efficient one-pot synthesis of propargylamines from Mannich bases through a retro-Mannich-type fragmentation
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An efficient one-pot synthesis of propargylamines is achieved by copper-catalyzed coupling of phenylacetylenes with Mannich bases through a chlorine(1+) or bromine(1+) ion-initiated retro-Mannich-type fragmentation under mild conditions. The Mannich bases are easily prepared from an electron-rich phenol, formaldehyde, and an amine. The protocol provides an appealing alternative for the construction of propargylamines by a simple one-pot procedure. Georg Thieme Verlag Stuttgart - New York.
- Zhu, Yefeng,Zhao, Huishuang,Wei, Yunyang
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p. 952 - 958
(2013/05/09)
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- Synthesis of [Zn(II)BHPPDAH] as new heterogeneous catalyst without being immobilized on any support and applied for mannich reaction
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In this paper, a novel heterogeneous complex of zinc with N,N-bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide(BHPPDAH) was synthesized. The catalyst was found to be a highly effective catalyst for the three-component coupling reactions of aldehydes, alkynes, and amines (A3 coupling) via C-H activation. The reactions could be applied to both aromatic and aliphatic aldehydes and alkynes. Nearly quantitative yields of the desired products were obtained in most cases. The reaction proceeds without any cocatalyst or activator, and water is the only byproduct. The catalyst was quantitatively recovered from the reaction by a simple filtration and reused for five cycles with almost consistent activity.
- Khalifeh, Reza,Sharghi, Hashem,Rashidi, Zahra
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p. 372 - 383
(2013/09/23)
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- A3-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films
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We decorated HS-functionalized cellulose nanocrystallite (CNC) films with monodisperse Au nanoparticles (AuNPs) to form a novel nanocomposite catalyst AuNPs@HS-CNC. The uniform, fine AuNPs were made by the reduction of HAuCl4 solution with thiol (HS-) group-functionalized CNC films. The AuNPs@HS-CNC nanocomposites were examined by X-ray photoelectron spectroscopy (XPS), TEM, ATR-IR and solid-state NMR. Characterizations suggested that the size of the AuNPs was about 2-3 nm and they were evenly distributed onto the surface of CNC films. Furthermore, the unique nanocomposite Au@HS-CNC catalyst displayed high catalytic efficiency in promoting three-component coupling of an aldehyde, an alkyne, and an amine (A3-coupling) either in water or without solvent. Most importantly, the catalyst could be used repetitively more than 11 times without significant deactivation. Our strategy also promotes the use of naturally renewable cellulose to prepare reusable nanocomposite catalysts for organic synthesis.
- Huang, Jian-Lin,Gray, Derek G.,Li, Chao-Jun
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p. 1388 - 1396
(2013/08/23)
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- Metal-free decarboxylative three-component coupling reaction for the synthesis of propargylamines
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A metal-free decarboxylative three-component coupling reaction was developed. When alkynyl carboxylic acids, paraformaldehyde, and amines were reacted in CH3CN at 65 °C for 3 h, the desired propargylamines were obtained in good yields. This coupling reaction also showed good yield in water solvent. This reaction showed higher selectivity toward alkynyl carboxylic acids than a terminal alkyne.
- Park, Kyungho,Heo, Yumi,Lee, Sunwoo
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supporting information
p. 3322 - 3325
(2013/07/26)
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- Nickel-catalyzed three-component coupling reaction of terminal alkynes, dihalomethane and amines to propargylamines
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Direct C - H and C - halogen activation is an important and practical task in C - C, C - N bond formation reactions using alkynes. Propargylic amines are synthetically versatile intermediates for the preparation of many nitrogen-containing biologically ac
- Lanke, Satish R.,Bhanage, Bhalchandra M.
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p. 729 - 733
(2013/12/04)
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