- Heterogeneous catalyzed aryl-nitrogen bond formations using a valine derivative bridged metal-organic coordination polymer
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A new 1D macrocyclic copper(ii) coordination polymer, [CuL2] (1, L = N-(4-pyridyl)-d,l-valine), based on a valine derived ligand was synthesized and characterized by single-crystal X-ray diffraction studies. The catalytic experiments showed tha
- Wu, Chuan-De,Li, Li,Shi, Lian-Xu
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Read Online
- 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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- A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib
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Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.
- Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.
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supporting information
p. 5222 - 5229
(2021/07/29)
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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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- Copper quinolate: A simple and efficient catalytic complex for coupling reactions
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We describe an effective and novel method to prepare N-aryl imidazoles via the copper quinolate-catalyzed N-arylation of aryl halides and imidazoles. A wide range of products were obtained in moderate to excellent yields under the optimal reaction conditions. Applying standard conditions, the model reaction could be performed on a gram scale. This method also presents a new avenue to the “click” reaction of terminal alkynes, benzyl bromide, and sodium azide and to the construction of C–C bonds by homocoupling of phenylboronic acid or phenylacetylene derivatives with the aid of copper quinolate.
- Wu, Fengtian,Li, Huiqin,Xie, Jianwei
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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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- Commercial drug norfloxacin as a novel ligand for the copper-catalyzed N-arylation of imidazole with aryl halides
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Norfloxacin was used as an efficient ligand for the CuBr-catalyzed C-N coupling reaction of imidazole and aryl halides. The protocol presented good functional group compatibility, permitting many aryl halides to react with imidazole to form the desired products in good to excellent yields.
- Wu, Fengtian,Nan, Chenlong,Ma, Minyang,Li, Huiqin,Xie, Jianwei
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- Cu-doped CoFe2O4 nanoparticles as magnetically recoverable catalyst for C–N cross-coupling reaction
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A new hybrid catalyst has been developed by immobilizing copper acetate onto surface of cobalt ferrite magnetic nanoparticles bearing N–O chelating ligand. The magnetic core of the catalyst was synthesized via ultrasound assisted co-precipitation method and characterized by FT-IR, XRD, EDX, SEM, TEM, TGA and VSM analysis. The catalyst was found to be very active for C–N bond forming reaction. Coupling of amines and aryl boronic acid could be achieved in high yield in methanol in presence of triethylamine at room temperature. After completion of the reaction the catalyst could be recovered using an external magnet and reused for consecutive catalytic cycles without significant decrease in the catalytic activity.
- Dutta, Mintu Maan,Phukan, Prodeep
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- Cu(II) complex of phenylthiosemicarbazone: An in situ catalyst for formation of C-N bond between different N-based neucleophiles with arylboronic acids at room temperature
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We have reported here a new synthetic protocol for the formation of C-N bond catalyzed by a thiosemicarbazone complex of copper. This in situ complex has been found to be very effective for Chan-Lam C-N cross-coupling reaction of anilines and various imidazoles at room temperature. Pyrazole and 4-bromoindole were also activated for C-N bond formation by using this protocol at room temperature. This catalytic system gave good-to-excellent yield using a mixture of DMF and water as solvent in a 1:1 proportion.
- Gogoi, Nibedita,Borah, Geetika,Gogoi, Pradip K.
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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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- Heterogeneous microwave-assisted Ullmann type methodology for synthesis of rigid-core ionic liquid crystals
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We present an efficient Ullmann-type synthesis methodology enabling the preparation of imidazolium compounds with an extended aromatic core in three steps. This procedure begins with a microwave-assisted, heterogeneously catalysed cross-coupling reaction
- Fouchet, Julien,Heinrich, Beno?t,L'Her, Matthieu,Voirin, Emilie,Karmazin, Lydia,Bailly, Corinne,Welter, Richard,Mirjafari, Arsalan,Douce, Laurent
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p. 10421 - 10431
(2018/06/18)
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- Carbothioamide as Highly Efficient Ligand for Copper-catalyzed Room Temperature Chan–Lam Cross-Coupling Reaction
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The catalytic activity of three N,S-donor ligands, viz L1 [2-(4-methoxybenzylidene)-N-phenylhydrazinecarbothioamide], L2 [2,2′-(1,2-diphenylethane-1,2-diylidene)bis(hydrazinecarbothioamide)] and L3 [2-(4-methoxybenzylidene)hydrazinecarbothioamide] has been reported for N-arylation of imidazoles with arylboronic acids in ethanol at room temperature. The method was found to be applicable in N-arylation for a wide range of electronically diverse arylboronic acids with imidazoles having modest to excellent isolated yields. The in situ generated copper(II) complex of the ligand namely, 2-(4-methoxybenzylidene)-N-phenylhydrazinecarbothioamide (L1) was found to be highly efficient homogeneous catalyst for N-arylation reaction.
- Baruah, Jayantajit,Gogoi, Kongkona,Dewan, Anindita,Borah, Geetika,Bora, Utpal
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p. 1203 - 1208
(2017/10/25)
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- Copper Oxide Nanoparticles as a Mild and Efficient Catalyst for N-Arylation of Imidazole and Aniline with Boronic Acids at Room Temperature
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The present work describes the excellent catalytic activity of copper(II) oxide nanoparticles (NPs) towards N-arylation of aniline and imidazole at room temperature. The copper(II)oxide NPs were synthesized by a thermal refluxing technique and characterized by FT-IR spectroscopy; powder XRD, SEM, EDX, TEM, TGA, XPS, BET surface area analysis, and particle size analysis. The size of the NPs was found to be around 12 nm having a surface area of 164.180 m 2 g -1.The catalytic system was also found to be recyclable and could be reused in subsequent catalytic runs without a significant loss of activity.
- Borah, Raju Kumar,Raul, Prasanta Kumar,Mahanta, Abhijit,Shchukarev, Andrey,Mikkola, Jyri-Pekka,Thakur, Ashim Jyoti
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p. 1177 - 1182
(2017/06/13)
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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 0106; 0107; 0108; 0109; 0110; 0111
(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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- 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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- Recyclable hydrophobic copper (II) phthalocyanine catalyzed N-arylation of imidazoles in dimethylsulfoxide
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Copper (II) phthalocyanine (CuPc) was used as a catalyst for the N-arylation of imidazoles with aryl iodides or bromides. The catalyst showed high activity and could be reused 3 times without any significant loss in activity. The catalyst was characterized by Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and ultraviolet-visible spectroscopy.
- Huang, Qiang,Zhou, Limei,Jiang, Xiaohui,Qi, Xiaolong,Wang, Zhonghua,Lang, Wencheng
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p. 1818 - 1824
(2015/09/28)
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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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- 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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- 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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- 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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- A highly efficient Cu-catalyst system for N-arylation of azoles in water
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6,7-Dihydroquinolin-8(5H)-one oxime (L3) was found to serve as a superior ligand for the CuI-catalyzed N-arylation of imidazoles with aryl iodides, bromides, and electron-deficient chlorides in water. Moreover, the CuI/L3 catalyst system enabled the coupling reactions to take place smoothly with high yields under a low catalyst loading (0.1-1 mol% CuI and 0.2-2 mol% L3).
- Wang, Deping,Zhang, Fuxing,Kuang, Daizhi,Yu, Jiangxi,Li, Junhua
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supporting information; experimental part
p. 1268 - 1271
(2012/06/04)
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- A versatile and efficient cu-catalyzed N-Arylation of aromatic cyclic secondary amines with aryl halides
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A copper-catalyzed coupling reaction of aryl halides with various aromatic cyclic secondary amines in DMSO has been developed efficiently. The versatile and efficient copper catalyst system is of wide-spread and practical application in cross-coupling reactions.
- Yang, Haitao,Miao, Zhiwei,Chen, Ruyu
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experimental part
p. 325 - 331
(2012/05/31)
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- A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water
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An efficient and convenient bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane has been developed for the cross-coupling of nitrogen heterocycles with aryl halides in water at moderate temperature. A variety of nitrogen nucleophiles including pyrazole, 7-azaindole, indazole, indole, pyrrole and imidazole afforded the corresponding products in moderate to good yields (up to 94%) under the described arylation conditions.
- Teo, Yong-Chua,Yong, Fui-Fong,Lim, Gina Shiyun
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supporting information; experimental part
p. 7171 - 7174
(2012/01/05)
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- Mild, base-free copper-catalyzed N-arylations of heterocycles using potassium aryltrifluoroborates in water under air
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An economic, mild and efficient copper-catalyzed methodology for the N-arylation of heterocycles was optimized using potassium aryltrifluoroborates in water.
- Joubert, Nicolas,Baslé, Emmanuel,Vaultier, Michel,Pucheault, Mathieu
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supporting information; experimental part
p. 2994 - 2997
(2010/07/10)
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- Mild conditions for copper-catalyzed N-arylation of imidazoles
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An efficient copper(I) bromide catalyzed N-arylation of azoles with a variety of aromatic bromides and iodides under mild conditions is reported. This reaction displayed great functional group compatibility and excellent reactive selectivity. Georg Thieme Verlag Stuttgart.
- Chen, Huaming,Wang, Deping,Wang, Xianyang,Huang, Wenlong,Cai, Qian,Ding, Ke
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experimental part
p. 1505 - 1511
(2010/09/14)
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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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- Ninhydrin: an efficient ligand for the Cu-catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides
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Cu2O/ninhydrin was found to be an efficient catalyst system for the N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl iodides, bromides and even unactivated chlorides to give the products in moderate to excellent yields.
- Huang, Yi-Zheng,Gao, Jin,Ma, Hong,Miao, Hong,Xu, Jie
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p. 948 - 951
(2008/09/17)
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- Benzotriazole: an excellent ligand for Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides
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Benzotriazole (BtH) is an efficient ligand for the Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides. A combination of CuI/BtH was found to be an efficient and inexpensive catalyst system to carry out the N-arylation of imidazoles affording the corresponding products in good to excellent yields.
- Verma, Akhilesh Kumar,Singh, Jaspal,Sankar, V. Kasi,Chaudhary, Ritu,Chandra, Ramesh
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p. 4207 - 4210
(2008/02/05)
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- Highly efficient and practical phosphoramidite-copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles
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A highly efficient copper-catalyzed system using phosphoramidite as ligands was applied to N-arylation of alkylamines and N(H)-heterocycles with aryl iodides and heteroaryl bromides. The reactions were carried out in relative mild conditions and good to excellent yields were obtained.
- Zhang, Zhanjin,Mao, Jincheng,Zhu, Di,Wu, Fan,Chen, Huilin,Wan, Boshun
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p. 4435 - 4443
(2007/10/03)
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- CuI catalyzed C-N bond forming reactions between aryl/heteroaryl bromides and imidazoles in [Bmim]BF4
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By using CuI as the catalyst and l-Proline as the ligand, the Ullmann-type coupling reactions of aryl/heteroaryl bromides and imidazoles in [Bmim]BF4 at 105-115 °C gave the corresponding N-arylimidazoles/N-heteroarylimidazoles in good yields. T
- Lv, Xin,Wang, Zhiming,Bao, Weiliang
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p. 4756 - 4761
(2007/10/03)
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- A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides
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CuI-catalyzed N-arylation of imidazoles with aryl bromides has been achieved in a near-homogeneous system that utilizes tetraethylammonium carbonate as base, 8-hydroxyquinoline as ligand, and H2O as cosolvent. Preliminary results with aryl chlo
- Liu, Longbin,Frohn, Mike,Xi, Ning,Dominguez, Celia,Hungate, Randy,Reider, Paul J.
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p. 10135 - 10138
(2007/10/03)
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- A simple copper salt catalysed the coupling of imidazole with arylboronic acids in protic solvent
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In the presence of a catalytic amount of a simple copper salt, the coupling of imidazole with arylboronic acids was performed in methanol to give corresponding N-arylimidazoles in almost quantitative yields; this coupling reaction could also be performed in aqueous solutions to give N-arylimidazoles in excellent yields.
- Lan, Jing-Bo,Chen, Li,Yu, Xiao-Qi,You, Jing-Song,Xie, Ru-Gang
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p. 188 - 189
(2007/10/03)
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