- Efficient nickel(II) immobilized on EDTA‐modified Fe3O4?SiO2 nanospheres as a novel nanocatalyst for amination of heteroaryl carbamates and sulfamates through the cleavage of C-O bond
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In this report, there was immobilized Nickel(II) on EDTA‐modified Fe3O4?SiO2 nanospheres and catalytic activity of which was described in the arylation reaction of nitrogen nucleophiles via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates. This protocol was applied to various nitrogen nucleophiles such as amines, anilines and N-heterocyclic compounds (pyrroles, indoles and imidazoles) in good to excellent yields. This reaction was promoted without the use of any external ligands under simple and mild conditions. The synthesized catalyst was well characterized by FT‐IR, XRD, TEM, FE-SEM, TGA, DLS,XPS, VSM, EDX, ICP and nitrogen adsorption-desorption isotherm analysis. The recycling studies revealed that the catalyst could be easily recovered by used the external magnetic field and directly reused for at least 7 times without the significant decrease in its catalytic activity.
- Dindarloo Inaloo, Iman,Eslahi, Hassan,Esmaeilpour, Mohsen,Majnooni, Sahar
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Read Online
- Synthesis and Physical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs)
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Tunable aryl alkyl ionic liquids (TAAILs) based on the imidazolium cation were first reported in 2009. Since then, a series of TAAILs with different properties due to the electron-donating or -withdrawing effect of the substituents at the aryl ring has be
- Lerch, Swantje,Strassner, Thomas
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supporting information
p. 15554 - 15557
(2021/10/06)
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- L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols
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A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield.
- Ding, Zhiqiang,Nie, Nan,Chen, Tian,Meng, Lingxin,Wang, Gongshu,Chen, Zhangpei,Hu, Jianshe
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supporting information
(2020/12/21)
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- Peripheral Ligand Effect on the Photophysical Property of Octahedral Iridium Complex: O-Aryl Substitution on the Phenyl Units of Homoleptic IrIII(C)3Complexes (CC = 1-Phenyl-3-methylimidazolin-2-ylidene- C, C2′) for Deep B
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To evaluate the efficacy of ortho-arylation in the second coordination sphere of octahedral iridium complex, a series of homoleptic N-heterocyclic carbene (NHC)-based Ir(CCR)3-type complexes were designed and prepared by introducing various substituents (
- Choi, Sunghan,Kang, Sang Ook,Kim, Jin-Hyoung,Kim, So-Yoen,Son, Ho-Jin
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p. 246 - 262
(2021/01/13)
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- N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst
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An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is
- Dindarloo Inaloo, Iman,Majnooni, Sahar,Eslahi, Hassan,Esmaeilpour, Mohsen
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p. 13266 - 13278
(2020/10/07)
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- Intercalation of copper salt to montmorillonite K-10 and its application as a reusable catalyst for Chan–Lam cross-coupling reaction
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A simple and efficient catalytic system has been developed by adsorption of copper salt in the interlayers of montmorillonite K-10. The catalytic system impressively exercises the green chemistry perspective leading to effortless recovery and recyclabilit
- Sarmah, Manashi,Dewan, Anindita,Boruah, Purna K.,Das, Manash R.,Bora, Utpal
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- Facile synthesis of hydrochar supported copper nanocatalyst for Ullmann C–N coupling reaction in water
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The exploration of inexpensive and stable heterogeneous catalysts and application of green solvents for Ullmann C–N coupling reaction remain challenging. We present a facile fabrication of copper nanoparticles on hydrochar as prepared from natural, inexpensive and renewable chitosan together with in-situ reduction of copper salt in a one-pot hydrothermal carbonization process. The copper nanoparticles were uniformly dispersed on hydrochar by choosing block copolymer F127 as surfactant. Moreover, maleic acid was introduced to improve the hydrophilicity of hydrochar. The most active copper nanocomposite catalyst, that is, Cu/HCS-MA-F127, exhibited excellent catalytic activity for Ullmann C–N coupling reaction in water. The nature of the Cu/HCS-MA-F127 was characterized by FTIR spectroscopy, TG, XRD, SEM and XPS. Moderate to excellent yields of aimed products were gained by using this catalytic strategy. Moreover, the Cu/HCS-MA-F127 catalyst can be reused by simple centrifugal recovery with a stable performance.
- Ge, Xin,Ge, Meng,Chen, Xinzhi,Qian, Chao,Liu, Xuemin,Zhou, Shaodong
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- Iron oxide encapsulated by copper-Apatite: An efficient magnetic nanocatalyst for: N-Arylation of imidazole with boronic acid
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N-Arylation of imidazole was carried out with various arylboronic acids on iron oxide encapsulated by copper-Apatite (Fe3O4?Cu-Apatite), producing excellent yields. Firstly, the iron nanoparticles were prepared using a solvothermal m
- Amadine, Othmane,Essamlali, Younes,Amedlous, Abdallah,Zahouily, Mohamed
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p. 36471 - 36478
(2019/11/20)
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- Expanding the Electrochemical Window: New Tunable Aryl Alkyl Ionic Liquids (TAAILs) with Dicyanamide Anions
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A set of new tunable aryl alkyl ionic liquids (TAAILs) based on the 1-aryl-3-alkyl imidazolium motif has been synthesized, in which the following variables were systematically changed: alkyl chain length, aryl substitution (group and position), and counte
- Lerch, Swantje,Strassner, Thomas
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p. 16251 - 16256
(2019/11/22)
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- A Newly Designed Carbohydrate-Derived Alkylamine Promotes Ullmann Type C-N Coupling Catalyzed by Copper in Water
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A green and biodegradable carbohydrate-derived alkylamine was designed and employed as ligand for Ullmann type C-N coupling catalyzed by copper in water. The coupling of aryl iodide and N-nucleophiles were examined and moderate to excellent yields were obtained. In addition, the in-water coupling strategy was expanded successfully to the reaction of indoles with 4-iodoanisole. By measuring the solubility, it is speculated that carbohydrate-derived alkylamine plays the role of chelating copper and promoting the dissolution of 4-iodoanisole in water. Remarkably, this methodology was environmentally friendly and economical because of the use of aqueous media in place of organic solvents.
- Zhou, Guoquan,Chen, Wen,Zhang, Shihui,Liu, Xuemin,Yang, Zehui,Ge, Xin,Fan, Hua-Jun
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supporting information
p. 193 - 198
(2019/01/14)
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- Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system
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A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.
- Janíková, Kate?ina,Jedinák, Luká?,Volná, Tereza,Canka?, Petr
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p. 606 - 617
(2018/01/01)
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- Dendrimer-encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N-arylation of nitrogen heterocycles and green synthesis of 5-substituted 1H-tetrazoles
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In this study, dendrimer-encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles were prepared via a multistep-synthesis. Then, the synthesized composite was fully characterized by various techniques such as fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), dynamic light scattering (DLS), UV-vis spectroscopy, energy dispersive X-ray analysis (EDX), thermogravimetric analysis (TGA) and vibration sample magnetometer (VSM). From the information gained by. FE-SEM and TEM studies it can be inferred that the particles are mostly spherical in shape and have an average size of 50?nm. Also, the amount of Cu is determined to be 0.51?mmol/g in the catalyst by inductively coupled plasma (ICP) analyzer. This magnetic nano-compound has been successfully applied as a highly efficient, magnetically recoverable and stable catalyst for N-arylation of nitrogen heterocycles with aryl halides (I, Br) and arylboronic acids without using external ligands or additives. The catalyst was also employed in a one-pot, three-component reaction for the efficient and green synthesis of 5-substituted 1H-tetrazoles using various aldehydes, hydroxylamine hydrochloride and sodium azide in water. The magnetic catalyst can be easily separated by an external magnet bar and is recycled seven times without significant loss of its activity.
- Esmaeilpour, Mohsen,Sardarian, Ali Reza,Firouzabadi, Habib
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- Cobalt-Catalyzed Hydroarylations and Hydroaminations of Alkenes in Tunable Aryl Alkyl Ionic Liquids
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Tunable aryl alkyl ionic liquids (TAAILs) are a promising class of imidazolium- or triazolium-based ionic liquids. Contrary to "standard" all-alkyl ionic liquids, these carry an aryl ring together with a linear or branched alkyl chain. Their application i
- Schroeter, Felix,Lerch, Swantje,Kaliner, Maria,Strassner, Thomas
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supporting information
p. 6215 - 6219
(2018/10/05)
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- Salen complex of Cu(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: an efficient and magnetically recoverable catalyst for N-arylation of imidazole with aryl halides
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Abstract: The Fe3O4@SiO2/Salen-Cu(II) nanocatalyst is reported as a thermally and air-stable, economical, and magnetically recoverable heterogeneous catalyst for the selective and efficient N-(hetero)arylation of imidazole. Only by adding a small amount of the catalyst (0.4?mol% Cu) to the reactants and heating under air, the new presented method provides a variety of functionalized and hindered N-(hetero)arylimidazoles in good to excellent yields within short reaction times. The catalyst could be easily recovered with the aid of a permanent magnet and reused up to five consecutive runs without significant loss of activity. Also, the leaching of Cu was negligible after the fifth recycle. Particularly, using either (hetero)aryl iodides or bromides as arylating agents and the need of only small amount of the magnetically recoverable heterogeneous copper-based nanocatalyst make this method low-cost, environmentally benign, and easy to use. Graphical abstract: [Figure not available: see fulltext.].
- Sardarian, Ali Reza,Zohourian-Mashmoul, Neda,Esmaeilpour, Mohsen
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p. 1101 - 1109
(2018/02/21)
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- Copper nanoparticles incorporated on a mesoporous carbon nitride, an excellent catalyst in the Huisgen 1,3-dipolar cycloaddition and N-arylation of N-heterocycles
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Cu nanoparticles with average particles size around 10?nm were incorporated on the surface of a mesoporous carbon nitride support. The XRD and N2 adsorption isotherms show that it maintains a hexagonal mesoporous structure with a high surface a
- Kazemi Movahed, Siyavash,Salari, Parinaz,Kasmaei, Melika,Armaghan, Mahsa,Dabiri, Minoo,Amini, Mostafa M.
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- Efficient Ullmann C-X coupling reaction catalyzed by a recoverable functionalized-chitosan supported copper complex
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Three different types of functionalized-CS were prepared and anchored with copper salts for use as the catalyst for the Ullmann C-X coupling reaction. The Schiff-basic chitosan supported copper complex (PCCS@CuI) exhibits the highest catalytic activity. The structure of the catalyst was characterized by FTIR spectroscopy, TG, XRD, SEM, EDS and XPS. This catalyst exhibited high applicability for the C-N and C-S coupling reactions, in which good to excellent yields were obtained. Its easy separation, good reusability and stability were notable.
- Liu, Xuemin,Chang, Shuo,Chen, Xinzhi,Ge, Xin,Qian, Chao
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supporting information
p. 16013 - 16020
(2018/10/04)
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- Chan-Lam-Type C-N Cross-Coupling Reactions under Base- and Ligand-Free CuI-Zeolite Catalysis
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Various representative copper(I)-exchanged zeolites were investigated for their catalytic potential in Chan-Lam cross-coupling reactions. CuI-USY appeared as the best catalyst and proved to efficiently promote C-N cross-coupling processes under attractive, simple, and practical conditions, namely refluxing in methanol under air and without any base.
- Garnier, Tony,Sakly, Randa,Danel, Mathieu,Chassaing, Stefan,Pale, Patrick
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supporting information
p. 1223 - 1230
(2017/03/11)
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- A N - aryl pyrazole compounds and N - aryl imidazole compound of preparation method
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The invention discloses a preparation method of an N-arylpyrazole compound and an N-arylimidazole compound. The method comprises the following steps: reacting at 20-120 DEG C for 6-48 hours by taking aryl halide and pyrazole or imidazole as substrates and copper salt as a catalyst in an organic solvent in the presence of alkali and a nitrogenous ligand under nitrogen protection; and after the reaction is finished, separating and purifying a reaction liquid to obtain the N-arylpyrazole compound or the N-arylimidazole compound. A product prepared by utilizing the method disclosed by the invention can not only be directly used, but also be used for other reactions as a substrate and has the advantages of moderation in adopted reaction condition, simple operation step and post-processing process, high yield and suitability for large-scale production.
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Paragraph 0099; 0100; 0101; 0102; 0103; 0104
(2017/10/05)
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- The Catalytic Properties of a Copper-Based Nanoscale Coordination Polymer Fabricated by a Solvent-Etching Top-Down Route
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Manipulating particle size is a powerful means of creating unprecedented applications in both inorganic and organic materials. Coordination polymers, which are emerging as a type of organic–inorganic hybrid materials, have attracted thriving interest in a variety of applications, but nanoscale coordination polymers have scarcely been touched. In this work, the pure-phase {Cu6[1,4-bis(imidazol-1-yl)butane]3I6}∞ coordination polymer with different sizes and morphologies was synthesized for the first time through a facile top-down route assisted by solvent etching. The size and morphology could be adjusted simply by varying the participating etching solvents. Our mechanistic investigations suggest that the bulk coordination polymer as a precursor in the etching solvents may experience a process of dispersion, dissolution, and recrystallization to generate the nanoscale counterpart. High catalytic activity of the nanoscale coordination polymer was observed in the N-arylation of imidazole aryl halides, and this was attributed to a high surface area and a low coordination number of unsaturated coordination sites. This simple and rapid preparation, requiring neither specialized equipment nor harsh conditions, suggests a wealth of potential for reducing the size of coordination polymers to comply with various practical applications.
- Cao, Xiaowei,Fang, Zhenlan,Huang, Wei,Ju, Qiang
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supporting information
p. 4803 - 4807
(2017/11/14)
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- Framework-Copper-Catalyzed C?N Cross-Coupling of Arylboronic Acids with Imidazole: Convenient and Ligand-Free Synthesis of N-Arylimidazoles
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A convenient and environmentally benign synthesis of N-arylimidazoles has been demonstrated by a straightforward reaction catalyzed by the unsaturated coordination sites of Cu in the copper terephthalate metal–organic framework (Cu(tpa)-MOF). A series of N-arylimidazoles has been synthesized in excellent yields by the C?N cross-coupling reaction of arylboronic acids and imidazoles catalyzed by the Cu(tpa)-MOF using ethanol as a benign solvent. The present ligand-free catalytic system proceeds smoothly under mild conditions, avoids stoichiometric Cu reagents, tolerates many functional groups, has a wide substrate scope, and is feasible with other nitrogen heterocycles. The stability and heterogeneity of the catalyst is evidenced by the results of a heterogeneity test, and the catalyst can be reused several times without a loss of activity. The easy preparation of the catalyst, its stability, recovery by simple filtration, and reusability reveal Cu(tpa) MOF as a versatile catalyst for academic and industrial applications.
- Devarajan, Nainamalai,Suresh, Palaniswamy
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p. 2953 - 2960
(2016/09/28)
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- Chan–Lam cross-coupling reactions promoted by anionic copper(I)/iodide species with cationic methyl-((pyridinyl)-pyrazolyl)pyridin-1-ium
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Four anionic ligands including 1-methyl-3(or 4)-(1-(pyridin-2-yl)-1H-pyrazol-3-yl)pyridin-1-ium iodide ([3,2′-pypzpym]I, [4,2′-pypzpym]I) and 1-methyl-3(or 4)-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)pyridin-1-ium iodide ([2,3′-pypzpym]I, [2,4′-pypzpym]I) are prepared. Reaction of CuI with [3,2′-pypzpym]I affords a mononuclear complex [CuI2(3,2′-pypzpym)] (1) and a one-dimensional coordination polymer [(Cu4I6)(3,2′-pypzpym)2]n(2). Analogous reactions of CuI with [4,2′-pypzpym]I, [2,3′-pypzpym]I or [2,4′-pypzpym]I yield [Cu4I6(4,2′-pypzpym)2] (3), [CuI2(2,3′-pypzpym)] (4) and [CuI2(2,4′-pypzpym)] (5), respectively. Relative to that of CuI, complexes 1–5 exhibit enhanced catalytic activities towards the Chan–Lam cross-coupling reactions of imidazole and arylboronic acids in a H2O[sbnd]MeCN (v/v=2:1). This catalytic system is involved in the C[sbnd]N cross-coupling reaction and works for a variety of imidazole derivatives as well as arylboronic acids with different electronic properties.
- Xue, Jiang-Yan,Li, Jun-Chi,Li, Hong-Xi,Li, Hai-Yan,Lang, Jian-Ping
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p. 7014 - 7020
(2016/10/14)
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- Tunable aryl alkyl ionic liquids with weakly coordinating bulky borate anion
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A series of 1-aryl 3-alkyl imidazolium tetrakis[bis-3,5(trifluoromethyl)phenyl]borate [BArF3,5] ionic liquids were synthesized and characterized. Increasing the alkyl chain length leads to lower melting points even resulting in room temperature
- Kaliner, Maria,Strassner, Thomas
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p. 3453 - 3456
(2016/07/18)
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- Microwave-promoted N-arylation of imidazole and amino acids in the presence of Cu2O and CuO in poly(ethylene glycol)
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Copper(I)-catalyzed N-arylation of imidazole with iodobenzene, its derivatives, and bromobenzene in poly(ethylene glycol) under microwave irradiation was studied. The influence of the following factors on the yield of arylation product was investigated: the nature of the source of copper and ligand, type of poly(ethylene glycol) (PEG) used, and substituents in iodoarene. An optimal catalytic system was selected: CuO/l-Hys/Cs2CO3/PEG-400, a possibility of recycling of copper-containing catalyst was demonstrated. N-Arylation of eight natural amino acids using catalysis with Cu2O/Cs2CO3/PEG-400 and microwave irradiation was studied, the dependence of the reaction results on temperature, duration of the process, and the ratio of the starting reagents was found. The highest yields of the target products were reached in the case of leucine, valine, and phenylalanine.
- Yakushev,Averin,Colacino,Lamaty,Beletskaya
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p. 1243 - 1248
(2017/02/05)
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- Efficient Ullmann C-N coupling catalyzed by a recoverable oligose-supported copper complex
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The natural compound β-cyclodextrin supported copper complex (CuIβ-CD) was prepared and employed as catalyst for an Ullmann-type C-N coupling reaction of N-nucleophiles and aryl halides under mild conditions. Reactions with different substrates were examined, and moderate to excellent yields were obtained. In addition to the high efficiency, the reaction system is also noticeable due to the excellent recoverability and reusability of the catalyst.
- Ge, Xin,Chen, Xinzhi,Qian, Chao,Zhou, Shaodong
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p. 58898 - 58906
(2016/07/06)
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- Palladium(II) 9,10-phenanthrenequinone N-substituted thiosemicarbazone/semicarbazone complexes as efficient catalysts for N-arylation of imidazole
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A series of palladium complexes, [PdCl(L1-4)] (1-4) (L1 = 9,10-phenanthrenequinone thiosemicarbazone, L2 = 9,10-phenanthrenequinone methylthiosemicarbazone, L3 = 9,10-phenanthrenequinone phenylthiosemicarbazone, and L4 = 9,10-phenanthrenequinone semicarbazone), have been synthesized and characterized by elemental analyses, UV-vis, FT-IR, 1H and 13C NMR, and ESI-Mass spectroscopic methods. The catalytic efficiency of the synthesized complexes was examined against N-arylation of imidazole. The system works well with the electron-rich, -neutral, and -deficient aryl halides to afford the products in good to excellent yields. Sterically congested aryl halides and heteroaryl halides have also been used as substrates to provide N-arylated heterocycles. In addition, this methodology can be applicable to other substrates with N-containing heterocycles.
- Anitha, Panneerselvam,Manikandan, Rajendran,Viswanathamurthi, Periasamy
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p. 3537 - 3550
(2015/09/28)
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- N-Arylation of Heterocycles Promoted by Cyclen Derivatives
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An efficient copper-catalyzed N-arylation reactions of imidazole, indole, and triazole with aryl or heteroaryl halides using cyclen derivatives as efficient organic base and ligand at moderate temperature have been investigated. The cross-couplings procee
- Zhang, Bao-Hua,Shi, Lan-Xiang,Liu, Si-Jie,Guo, Rui-Xia
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p. 1234 - 1239
(2015/08/06)
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- Catalytic activity and antibacterial properties of nanopolymer-supported copper complex for C-N coupling reactions of amines and nitrogen-containing heterocycles with aryl halides
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This paper reports on the antibacterial properties and application of nanopolymer-supported copper complex for the ligand-free C-N coupling reactions of amines and nitrogen-containing heterocycles with aryl halides. This method has the advantages of high yields, simple methodology, and easy workup. The catalyst can be recovered by simple filtration from the reaction mixture and reused several times without significant loss of catalytic activity.
- Nasrollahzadeh, Mahmoud,Zahraei, Ali,Pourbasheer, Eslam
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p. 1329 - 1334
(2015/08/18)
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- A simple and efficient 2N2O-Cu(II) complex as a catalyst for N-arylation of imidazoles in water
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Four inexpensive and air- and moisture-stable 2N2O-Cu complexes were synthesized, one of which proved to exhibit good catalytic activity for the N-arylation of imidazoles in water. A variety of aryl iodides and aryl bromides underwent coupling with imidazoles promoted by the catalytic system with moderate to excellent yields.
- Liu, Yashuai,Gu, Ningning,Liu, Ping,Xie, Jianwei,Dai, Bin,Liu, Yan
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p. 468 - 470
(2015/06/30)
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- Open-air N-arylation of N-H heterocycles with arylboronic acids catalyzed by copper(II) Schiff base complexes
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Two copper Schiff base complexes, in both homogeneous and heterogeneous forms, were prepared and characterized by using elemental analysis, FTIR, UV-Vis spectroscopy and scanning electron microscopy. The catalytic performances of these complexes were studied in the N-arylation of N-H heterocycles with arylboronic acids in methanol without any added base at 40 °C under open air. The effects of various parameters such as solvent and temperature on the reaction system were studied. The reaction is applicable to a wide variety of N-H heterocycles and arylboronic acids. The heterogeneous catalyst was recovered by simple filtration, and reusability experiments showed that this catalyst can be used five times without much loss in the catalytic activity.
- Islam,Dey, Ram Chandra,Roy, Anupam Singha,Paul, Sumantra,Mondal, Sanchita
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p. 961 - 969
(2015/01/09)
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- A highly active reusable polymer anchored copper catalyst for C-O, C-N and C-S cross coupling reactions
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A new furfural functionalized polymer-amine grafted with copper catalyst has been designed and employed for the N-arylation, O-arylation and S-arylation reactions under an open air condition to afford the corresponding coupled products in good to excellent yields. This solid supported catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), UV-vis spectroscopy and scanning electron microscope (SEM). The developed catalyst can be facilely recovered and reused five times without significant decrease in activity and selectivity. This result confirms that the polymer anchored complex was not leached during the reaction, suggesting the true heterogeneous nature of the catalyst.
- Islam, Sk.Manirul,Salam, Noor,Mondal, Paramita,Roy, Anupam Singha,Ghosh, Kajari,Tuhina
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- Copper complex-catalysed C-N coupling reaction of aryl iodides with nitrogen-containing heterocycles
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An efficient method for the copper-catalysed arylation of nitrogen-containing heterocycles is reported using 3-(diphenylphosphino) propanoic acid as a ligand in combination of CuCl. The C-N coupling reactions afford various N-arylated products in good to excellent yields.
- Sajadi, S. Mohammad,Maham, Mehdi
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p. 128 - 129
(2014/03/21)
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- 3-(Diphenylphosphino)propanoic acid: An efficient ligand for the Cu-catalyzed N-arylation of imidazoles and 1H-pyrazole with aryl halides
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3-(Diphenylphosphino)propanoic acid (L2) has proved to be an efficient ligand for the copper-catalyzed CN coupling reactions. N-arylation of imidazoles with aryl iodides catalyzed by CuCl/L2 was smoothly carried out in DMSO at 100 °C with a yield up to 98%. N-arylation of 1H-pyrazole with aryl iodides and bromides catalyzed by Cu(OAc)2/L2 in 1,4-dioxane also gave the corresponding products with yields of 40%-98%.
- Liu, Ya-Shuai,Liu, Yan,Ma, Xiao-Wei,Liu, Ping,Xie, Jian-Wei,Dai, Bin
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p. 775 - 778
(2014/06/09)
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- A facile one-step approach for the synthesis of uniform spherical Cu/Cu2O nano- and microparticles with high catalytic activity in the Buchwald-Hartwig amination reaction
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In the present work, we have developed a rapid, one step, calcination-free protocol for the synthesis of uniform spherical Cu/Cu2O nano/microparticles (NMPs). The synthesis of Cu/Cu2O NMPs was achieved by microwave irradiation of copper acetate as a precursor and 1,4-butanediol as a solvent in a few minutes. The prepared Cu/Cu2O NMPs gave 100% yield of uniform spherical morphology. 1,4-Butanediol plays a crucial role in reactions such as a solvent, reactant, stabilizer and capping agent which control the crystal morphology. The resultant product was characterized with the help of different techniques such as XRD, FEG-SEM, EDS, TEM, FT-IR, TPR, DSC-TGA, XPS and BET surface area analysis. The results confirm that the Cu/Cu2O NMPs had good crystallinity and were essentially pure. This is a simple, faster, inexpensive and additive-free protocol for synthesis of nanocrystalline Cu/Cu2O compared to the conventional method. These Cu/Cu2O NMPs showed excellent catalytic activity in the Buchwald-Hartwig amination coupling reaction. Notably the reaction does not require any ligand source, and requires low catalyst loading, and low temperature with catalyst recyclability. the Partner Organisations 2014.
- Bhosale, Manohar A.,Bhanage, Bhalchandra M.
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p. 15122 - 15130
(2014/04/17)
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- Two-dimensional copper-based metal-organic framework as a robust heterogeneous catalyst for the N-arylation of imidazole with arylboronic acids
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N-arylation of imidazole was accomplished with a two-dimensional (2D) [Cu(ima)2]n metal-organic framework in methanol at room temperature. A variety of N-arylimidazoles were isolated in good yields after a short reaction time. Moreov
- Li, Zhao-Hao,Xue, Li-Ping,Wang, Lei,Zhang, Shuai-Tao,Zhao, Bang-Tun
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p. 119 - 121
(2013/02/25)
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- An unusual 30-membered copper(i) cluster derived from the C-S bond cleavage and its use in heterogeneous catalysis
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The Cu(i)-mediated C-S bond cleavage of 5-methyl-4-(p-tolyl)pyrimidine-2- thiol (mtpmtH) gave one 30-nuclear cluster [Cu30I16(mtpmt) 12(μ10-S4)], one polymeric complex [(bmtpms)Cu-(μ-I)]n and one tetranuclear complex [(bmptmds){Cu(μ-I)}2]2; the 30-nuclear cluster displayed excellent catalytic performances in the coupling reactions of N-heterocycles and arylboronic acids and could be recycled and reused.
- Li, Hong-Xi,Zhao, Wei,Li, Hai-Yan,Xu, Zhong-Lin,Wang, Wen-Xia,Lang, Jian-Ping
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supporting information
p. 4259 - 4261
(2013/07/05)
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- Efficient copper-catalyzed ullmann reaction of aryl bromides with imidazoles in water promoted by a pH-Responsive ligand
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A series of 1,10-phenanthroline derivatives were used as supporting ligands for copper-catalyzed Ullmann reaction in neat water. The catalytic system based on 4,7-dihydroxy-1,10-phenanthroline has demonstrated the promising catalytic performances for aryl
- Lv, Rui,Wang, Yangxin,Zhou, Chunshan,Li, Liuyi,Wang, Ruihu
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p. 2978 - 2982
(2013/10/21)
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- A versatile approach to ullmann C-N couplings at room temperature: New families of nucleophiles and electrophiles for photoinduced, copper-catalyzed processes
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The use of light to facilitate copper-catalyzed cross-couplings of nitrogen nucleophiles can enable C-N bond formation to occur under unusually mild conditions. In this study, we substantially expand the scope of such processes, establishing that this approach is not limited to reactions of carbazoles with iodobenzene and alkyl halides. Specifically, we demonstrate for the first time that other nitrogen nucleophiles (e.g., common pharmacophores such as indoles, benzimidazoles, and imidazoles) as well as other electrophiles (e.g., hindered/deactivated/heterocyclic aryl iodides, an aryl bromide, an activated aryl chloride, alkenyl halides, and an alkynyl bromide) serve as suitable partners. Photoinduced C-N bond formation can be achieved at room temperature using a common procedure with an inexpensive catalyst (CuI) that does not require a ligand coadditive and is tolerant of moisture and a variety of functional groups.
- Ziegler, Daniel T.,Choi, Junwon,Munoz-Molina, Jose Maria,Bissember, Alex C.,Peters, Jonas C.,Fu, Gregory C.
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supporting information
p. 13107 - 13112
(2013/09/24)
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- Cu-grafted mesoporous organic polymer: A new recyclable nanocatalyst for multi-component, N-arylation and S-arylation reactions
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A new mesoporous Cu-MPTA-1 nanocatalyst has been synthesized via a simple and facile in situ radical polymerization of triallylamine in the presence of an organic-organic self-assembly of anionic surfactant SDS, followed by grafting of Cu(ii) at room temperature under an inert atmosphere. This nanomaterial has been characterized by elemental analysis, powder X-ray diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), UV-vis diffuse reflectance spectroscopy (DRS), thermogravimetric analysis (TGA), N2 adsorption-desorption studies, X-ray photoelectron spectroscopy (XPS) and EPR spectroscopy. Cu-MPTA-1 acts as an efficient heterogeneous nanocatalyst exhibiting a high catalytic activity for N-arylation and S-arylation reactions using water as a green solvent and also exhibits an excellent catalytic activity for the one-pot synthesis of propargylamines via a three component coupling of an alkyne, an amine and an aldehyde at room temperature. Moreover, the catalyst is easily recoverable and can be reused six times without an appreciable loss of catalytic activity in the three component coupling reaction. The highly dispersed Cu(ii) sites in the Cu-grafted mesoporous polymer could be responsible for the observed high activities of the Cu-MPTA-1 catalyst in the coupling reactions. No evidence of leached Cu from the catalyst during the course of the reaction has been observed, suggesting true heterogeneity in the catalytic process. The Royal Society of Chemistry.
- Salam, Noor,Kundu, Sudipta K.,Roy, Anupam Singha,Mondal, Paramita,Roy, Susmita,Bhaumik, Asim,Islam, Sk. Manirul
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p. 3303 - 3316
(2013/12/04)
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- Synthesis and crystal structures of coordination complexes containing Cu2I2 units and their application in luminescence and catalysis
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The reaction of bis- or tris-chelating nitrogen-containing ligands (L1-L5) with CuI gave rise to five coordination complexes consisting of Cu 2I2 dimeric units. L1 in complex 1 adopts a cis conformation and links Cu2I2 into a dinuclear structure. L2 and L3 in complexes 2 and 3 exhibit a trans conformation, and the alternative linkage of L2 or L3 and Cu2I2 results in the formation of a 1D chain. In complex 4, two pyrazolyl-pyridine units of L4 at the same side of the central phenyl ring are connected to Cu2I2 forming a tetranuclear macrocycle, and the third pyrazolyl-pyridine unit at the other side of the central phenyl ring further links the macrocycle into a 1D chain. L5 bridges Cu2I2 in a cis conformation forming a tetranuclear complex, which is very different from 1 owing to the difference of the electronic property between pyrazolyl and triazolyl rings. The coordination nitrogen atoms in two pairs of ortho-positioned nitrogen-containing chelating rings in L1 and L5 are directed toward opposite and the same directions, respectively. Complexes 1-4 containing pyrazolyl-pyridine units showed luminescence whereas no clear emission was observed in complex 5 containing triazolyl-pyridine units, despite the fact that they were investigated under the same conditions. The application of complexes 1-5 in the copper(I)-catalyzed Ullmann cross-coupling reaction and azide-alkyne cycloaddition reaction was preliminarily evaluated. Making a difference: Five copper(I) complexes consisting of Cu2I2 units (see figure for example) have been prepared by using readily available bis- or tris-chelating nitrogen-containing ligands. These complexes possess different crystal structures, luminescence properties, and catalytic performances owing to the difference in steric and electronic properties of the organic ligands. Copyright
- Zhao, Huaixia,Li, Xinxiong,Wang, Jinyun,Li, Liuyi,Wang, Ruihu
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p. 1491 - 1502
(2014/01/06)
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- A reusable polymer supported copper catalyst for the C-N and C-O bond cross-coupling reaction of aryl halides as well as arylboronic acids
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A simple and industrially viable protocol for C-N and C-O coupling was reported here. The polymer supported heterogeneous copper catalyst was prepared from chloromethyl polystyrene using a simple procedure. O-Arylation of substituted phenols with various aryl halides was achieved using this copper catalyst in DMSO medium. This heterogeneous copper catalyst, also efficiently works for the N-arylation of N-H heterocycles with aryboronic acids in methanol. This catalyst was also effective in amination reaction of primary amines with aryl halides as well as arylboronic acids in DMSO medium. The effects of solvent, base and temperature for the O-Arylation and amination reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to several times without sufficient loss of its catalytic activity.
- Islam, Sk.Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina,Salam, Noor,Mobarak, Manir
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experimental part
p. 4264 - 4274
(2012/01/06)
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- Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water
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Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-fr
- Inamoto, Kiyofumi,Nozawa, Kanako,Kadokawa, Jun,Kondo, Yoshinori
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experimental part
p. 7794 - 7798
(2012/09/22)
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- SiO2-NHC-CuI-catalyzed N-arylation of imidazoles with arylboronic acids under base-free reaction conditions
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(Chemical Equation Presented) N-Arylation of imidazoles with arylboronic acids was efficiently carried out in the presence of a catalytic amount of SiO2-NHC-CuI in methanol at room temperature under base-free reaction conditions. The reactions of a variety of arylboronic acids with imidazoles generated the corresponding products N-arylimidazoles in good to excellent yields. In addition, SiO2-NHC-CuI could be recovered and recycled for six consecutive trials without significant loss of its reactivity. Copyright Taylor & Francis Group, LLC.
- Liu, Ping,Li, Pinhua,Wang, Lei
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experimental part
p. 2595 - 2605
(2012/07/30)
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- An efficient polymer-supported copper(II) catalyst for the N-arylation reaction of N(H)-heterocycles with aryl halides as well as arylboronic acids
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Immobilization of copper onto polystyrene provided a polymer-supported copper(II) catalyst, which was effective in cross-coupling reactions between N-containing substrates and arylboronic acids using methanol as a solvent in air under base-free conditions
- Islam, Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Salam, Noor,Paul, Sumantra,Hossain, Dildar,Mobarok, Manir
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experimental part
p. 447 - 458
(2012/03/10)
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- An efficient recyclable polymer supported copper(II) catalyst for C-N bond formation by N-arylation
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Polymer supported Cu(II) catalyst was prepared, characterized and employed for the N-arylation and amination reaction of N-H heterocycles with aryl halides as well as arylboronic acids to afford the corresponding coupled products in good to excellent yields. This catalyst can be used several times with consistent catalytic activity.
- Islam, Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Mobarok, Manir,Paul, Sumantra,Salam, Noor,Hossain, Dildar
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experimental part
p. 1171 - 1181
(2012/06/18)
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- A reusable polymer supported copper(I) complex for the C-N bond cross-coupling reaction
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The Ullmann coupling of amines with aryl iodide as well as arylboronic acids and N(H)-heterocycles with arylboronic acids has been carried out efficiently using PS-LCu(I) catalyst. The copper complex has been prepared and characterized by using scanning electron microscope (SEM), elemental analysis, atomic absorption spectroscopy (AAS), Thermo gravimetric analysis and spectrometric methods like Fourier transform infrared spectroscopy (FTIR). The effects of various parameters such as temperature, solvent and base on the reaction system were studied. The reusability experiments show that the catalyst can be used five times without much loss in the catalytic activity.
- Islam,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Mobarok, Manir
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experimental part
p. 1352 - 1357
(2011/10/12)
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- Cross coupling of arylboronic acids with imidazoles by sulfonatocopper(II) (salen) complex in water
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A mild and clean protocol for the cross coupling reactions between imidazoles and arylboronic acids has been developed in good to excellent yields up to 98% in the presence of sulfonatocopper(II)(salen) catalyst in water without addition of other additives and bases.
- Wang, Lixia,Jiang, Zhaoqiong,Yu, Lintao,Li, Lili,Li, Zhengkai,Zhou, Xiangge
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supporting information; experimental part
p. 764 - 765
(2011/01/11)
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- Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents
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A broad range of highly enantioenriched 2-acylimidazoles are synthesized by palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of 2-imidazolo-substituted enol carbonates. The enantioenriched 2-acylimidazole products can easily be converted to the corresponding carboxylic acid, ester, amide, and ketone derivatives with complete retention of the enantiopurity. The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil.
- Trost, Barry M.,Lehr, Konrad,Michaelis, David J.,Xu, Jiayi,Buckl, Andreas K.
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supporting information; experimental part
p. 8915 - 8917
(2010/08/22)
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- Cu-Al hydrotalcite: An efficient and reusable ligand-free catalyst for the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines
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Copper-aluminum hydrotalcite catalysts were effectively used in the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines to afford the corresponding N-alkylated/arylated amines in excellent yields. The catalyst was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles with almost consistent activity. Georg Thieme Verlag Stuttgart.
- Sreedhar,Arundhathi,Linga Reddy,Amarnath Reddy,Lakshmi Kantam
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experimental part
p. 2517 - 2522
(2010/03/24)
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- Microwave-assisted solvent-free N-arylation of imidazole and pyrazole
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Solvent-free coupling reactions between imidazole or pyrazole and aryl bromides were achieved with microwave irradiation using copper salts and l-amino acids as catalysts.
- Chow, Wai Shan,Chan, Tak Hang
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scheme or table
p. 1286 - 1289
(2009/09/06)
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- Highly functional group tolerance in copper-catalyzed N-arylation of nitrogen-containing heterocycles under mild conditions
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A copper-catalyzed process has been developed for the N-arylation reaction under very mild conditions in the absence of additional ligand. This protocol could not only tolerate an array of thermally sensitive functional groups, but also achieve high chemoselectivity.
- Zhu, Liangbo,Li, Gaocan,Luo, Liang,Guo, Peng,Lan, Jingbo,You, Jingsong
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supporting information; experimental part
p. 2200 - 2202
(2009/07/01)
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