- Copper- and amine-free Sonogashira reaction of N,N-disubstituted propargylamine: Synthesis of substituted aryl propargylamine
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A copper- and amine-free Sonogashira reaction of N,N -disubstituted propargylamine (DEP) is reported. The procedure was mild and tolerated a series of aryl bromides, affording the substituted aryl propargylic amines in good to excellent yield. Copyright T
- Zhang, Weiwei,Cheng, Jiang,Ding, Linya,Zhong, Ping,Zhao, Li,Wu, Huayue
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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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- Microwave-promoted, solvent-free, three-component coupling of aldehyde, alkyne, and amine catalyzed by AgNO3
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An efficient three-component coupling reaction of alkyne, aldehyde, and amine was carried out in one pot smoothly under the catalysis of AgNO3 and microwave irradiation. The scope of reaction substrates was extended. Moreover, the reaction can be performe
- He, Tingting,Zha, Zhenggen,Pan, Chongfeng,Wang, Zhiyong
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Read Online
- Heterogeneous catalyst Cu@COF-Me-M as well as preparation method and application thereof
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The invention particularly relates to a heterogeneous catalyst Cu@COF-Me-M as well as a preparation method and application thereof. An existing heterogeneous catalyst is low in diffusion speed and high in preparation difficulty. The invention provides a heterogeneous catalyst Cu@COF-Me-M, which is prepared by adding a compound shown in a formula I and triformyl phloroglucinol serving as raw materials into a mesitylene, dimethyl sulfoxide and acetic acid reaction system, heating, reacting, and cooling to room temperature to obtain a covalent organic framework COF-Me-M, and reacting with copper chloride to obtain the Cu@COF-Me-M. the heterogeneous catalyst can effectively catalyze a three-component coupling reaction. The heterogeneous catalyst is simpler in preparation process, low in dosage, high in catalytic efficiency and convenient to recover, and has important significance in industrial production.
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Paragraph 0079-0082
(2021/04/14)
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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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- 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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- 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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- 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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- 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 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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- 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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- Copper(II)-Schiff Base Complex-Functionalized Polyacrylonitrile Fiber as a Green Efficient Heterogeneous Catalyst for One-Pot Multicomponent Syntheses of 1,2,3-Triazoles and Propargylamines
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A series of copper(II)-Schiff bases-functionalized polyacrylonitrile fiber catalysts were successfully prepared using copper acetate as copper source and characterized by elemental analysis, fourier-transfer infrared spectroscopy, ultraviolet-visible spectroscopy, X-ray photoelectron spectroscopy and inductively coupled plasma analysis. Excellent physical strength and thermal stability of the fiber catalysts were demonstrated by scanning electron microscopy, X-ray diffraction, thermogravimetric/differential scanning calorimetry analysis and mechanical strength measurements. Furthermore, these catalysts were successfully applied to one-pot multicomponent copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and aldehyde, alkyne, amine (A3) coupling reaction in which the influences of different substituent groups on the catalytic activities of fiber catalysts were investigated in detail. Among them, the bis[N-ethyl-3,5-di-tert-butyl-salicylideneiminato]copper(II)-functionalized polyacrylonitrile fiber (PANS2F?Cu) as a green, efficient catalyst exhibited the best catalytic activity for its high hydrophobic micro-environment can aggregate the reactants to the catalytic sites and accelerate the reaction. In addition, the PANS2F?Cu has performed well in scaled-up experiment and shown excellent recyclability (at least ten times), and these enable it to have great potential for further applications. (Figure presented.).
- Li, Pengyu,Liu, Yuanyuan,Wang, Lu,Xiao, Jian,Tao, Minli
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p. 1673 - 1684
(2018/03/21)
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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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- 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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- Well-defined dinuclear silver phosphine complexes based on nitrogen donor ligand and their high efficient catalysis for A3-coupling reaction
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Nitrogen donor ligands HL1, HL3, HL4 and their silver complexes 1·OTf–4·OTf are prepared and fully characterized. Treatment of HL1-HL4 with AgOTf (OTf??=?triflato) in presence of base Etsu
- Chen, Jing-Jing,Gan, Zhi-Liang,Huang, Qi,Yi, Xiao-Yi
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- Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines
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A reduction of various aryl, alkyl, and α,β-unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism.
- Chardon, Aurélien,Mohy El Dine, Tharwat,Legay, Rémi,De Paolis, Micha?l,Rouden, Jacques,Blanchet, Jér?me
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p. 2005 - 2009
(2017/02/19)
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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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- 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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- 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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- 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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- 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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- Catalyst-free activation of methylene chloride and alkynes by amines in a three-component coupling reaction to synthesize propargylamines
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Propargylamines are synthesized via metal-free activation of the C-halogen bond of dihalomethanes and the C-H bond of terminal alkynes in a three-component coupling without catalyst or additional base and under mild reaction conditions. The dihalomethanes
- Rawat, Vikas S.,Bathini, Thulasiram,Govardan,Sreedhar, Bojja
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supporting information
p. 6725 - 6729
(2014/08/18)
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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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- 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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- 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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- 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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- 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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- Three-component coupling of aldehydes, amines, and alkynes catalyzed by oxidized copper nanoparticles on titania
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Copper nanoparticles (mainly as Cu2O) on titania have been shown to catalyze the multicomponent synthesis of propargylamines from aldehydes, amines, and alkynes (A3 coupling) effectively at 70 °C under solvent-free conditions. Both aromatic and aliphatic aldehydes and alkynes have been combined with secondary amines to provide a wide range of propargylamines in moderate to excellent yields. Two examples of ketone/amine/alkyne (KA 2) coupling are also included. The catalyst is easy to prepare, reusable at a low copper loading (0.5 mol-%), and exhibits higher catalytic activity than some commercially available copper sources. Some mechanistic aspects of the reaction have also been examined, which have unveiled the participation of copper(I) acetylides in a heterogeneous process. Copyright
- Albaladejo, Maria Jose,Alonso, Francisco,Moglie, Yanina,Yus, Miguel
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experimental part
p. 3093 - 3104
(2012/06/30)
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- Cobalt-catalyzed alkyne-dihalomethane-amine coupling: An efficient route for propargylamines
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A cobalt-catalyzed three-component coupling of terminal alkynes, dihalomethanes, and amines was developed. This method offers an efficient way for propargylamines via the dual activation of C-H and C-halogen bond. The reaction uses cheap CoBr2
- Tang, Yanchi,Xiao, Tiebo,Zhou, Lei
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supporting information
p. 6199 - 6201,3
(2012/12/12)
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- PROPARGYLAMINE SYNTHESIS USING A COPPER (I) CATALYSED THREE COMPONENT COUPLING REACTION
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The present invention relates to a three component coupling reaction. In this reaction a terminal alkyne or a salt thereof, a geminal dihalide and a primary or secondary amine are reacted in the presence of a copper (I) catalyst to produce a propargylamin
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Page/Page column 8; 12
(2012/02/01)
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- Efficient iron(iii)-catalyzed three-component coupling reaction of alkynes, CH2Cl2 and amines to propargylamines
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An iron(iii)-catalyzed three-component coupling reaction of alkynes, CH2Cl2 and amines was developed for facile synthesis of propargylamines. Preliminary mechanism investigation using in situ FT-IR reveals that the crucial Fe-acetyli
- Gao, Jian,Song, Qing-Wen,He, Liang-Nian,Yang, Zhen-Zhen,Dou, Xiao-Yong
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supporting information; experimental part
p. 2024 - 2026
(2012/03/27)
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- Copper-catalyzed three-component coupling of terminal alkyne, dihalomethane and amine to propargylic amines
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The direct C-H and C-halogen activation for C-C bond formation is one of the most interesting reactions in organic chemistry. C-C bond formation using alkynes as a carbon nucleophilic source is a very useful method in synthesis. Herein, a copper(I) chlori
- Yu, Dingyi,Zhang, Yugen
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experimental part
p. 163 - 169
(2011/03/22)
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- Mesoporous SBA-15 supported silver nanoparticles as environmentally friendly catalysts for three-component reaction of aldehydes, alkynes and amines with glycol as a "green" solvent
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The mesoporous SBA-15 supported silver nanoparticles catalyst system with a highly ordered hexagonal mesostructure was prepared by an in situ reduction method using hexamethylenetetramine as mild and efficient reducing agent. These AgSBA-15 materials act
- Yong, Guo-Ping,Tian, Dong,Tong, Hong-Wu,Liu, Shao-Min
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experimental part
p. 40 - 44
(2010/09/04)
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- Effects of a flexible alkyl chain on an imidazole ligand for copper-catalyzed mannich reactions of terminal alkynes
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Copper-catalyzed Mannich reactions of terminal alkynes and secondary amines with aqueous formaldehyde can be accelerated by the use of a catalytic amount of an imidazole ligand carrying a long alkyl chain. The alkyl chain shows an efficient steric effect
- Okamura, Takaaki,Asano, Keisuke,Matsubara, Seijiro
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experimental part
p. 3053 - 3056
(2011/02/25)
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- Palladium-catalyzed cross-coupling reaction of aryl trimethoxysilanes with terminal alkynes
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A palladium-catalyzed cross-coupling reaction of aryl trimethoxysilanes with terminal alkynes was described. Thus, di-substituted alkynes were prepared in moderate to good yields. The electron-deficient terminal alkynes also worked well in the procedure.
- Ye, Zhishi,Liu, Miaochang,Lin, Baoda,Wu, Huayue,Ding, Jinchang,Cheng, Jiang
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scheme or table
p. 530 - 532
(2009/04/14)
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- Silver nanoparticles supported by novel nickel metal-organic frameworks: An efficient heterogeneous catalyst for an A3 coupling reaction
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A novel heterogeneous catalyst of silver nanoparticles was prepared by using a nickel metal-organic framework (Ni-MOF) as a template. The catalyst has a very high catalytic activity and a strict structural selectivity towards linear aliphatic aldehydes in
- Wang, Sujing,He, Xiaoxiao,Song, Lexin,Wang, Zhiyong
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scheme or table
p. 447 - 450
(2009/07/25)
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- Synthesis of mono- and 1,3-disubstituted allenes from propargylic amines via palladium-catalysed hydride-transfer reaction
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Mono- and 1,3-disubstituted allenes were synthesized from the corresponding propargylamines via palladium-catalysed hydride-transfer reaction. In the current transformation, propargylic amines can be handled as allenyl anion equivalents and introduced int
- Nakamura, Hiroyuki,Ishikura, Makoto,Sugiishi, Tsuyuka,Kamakura, Takaya,Biellmann, Jean-Francois
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experimental part
p. 1471 - 1477
(2008/10/09)
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- Reusable polymer-anchored amino acid copper complex for the synthesis of propargylamines
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An amino acid was anchored to chloroacetylated polystyrene beads and the polymeric ligand containing N, O donor sites was treated with a solution of Cul to form the supported copper complex. The one-pot synthesis of propargylamines was then achieved efficiently via a three-component coupling of aldehydes, alkynes and amines using the supported copper catalyst under mild conditions. The catalyst could be recovered by simple filtration and reused several times without significant loss of activity.
- Wang, Liang,Cai, Chun
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experimental part
p. 538 - 541
(2009/04/06)
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- A facile solvent-free one-pot three-component Mannich reaction of aldehydes, amines and terminal alkynes catalysed by CuCl2
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A solventless Mannich condensation of aldehydes, amines, and terminal alkynes catalysed by 10 mol% of CuCl2 was investigated. The components were simply mixed and heated together under vacuum, without any need of solid-support or solvent. This results in the formation of Mannich products in high yields.
- Sharifi, Ali,Mirzaei, Mojtaba,Naimi-Jamal, M. Reza
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p. 129 - 132
(2008/02/05)
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- Alkynylation of aryl bromides with propargylamines catalyzed by a palladium-tetraphosphine complex
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The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for the alkynylation of aryl bromides with propargylamines. Higher reactions rates were observed with N,N- dialkylpropargylamines than with N-methylpropargylamine or propargy lamine. A wide variety of substituents such as alkyl, phenyl, methoxy, dimethylamino, fluoro, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, or nitrile, on the aryl bromides are tolerated. High turnover numbers can be obtained with most of these aryl bromides. The coupling reaction of sterically very congested aryl bromides such as 9-bromoanthracene or 2,4,6- triisopropylbromobenzene also proceeds in good yields. Georg Thieme Verlag Stuttgart.
- Lemhadri, Mhamed,Doucet, Henri,Santelli, Maurice
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p. 1359 - 1367
(2007/10/03)
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