- 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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- Core-shell Cu2S:NiS2@C hybrid nanostructure derived from a metal-organic framework with graphene oxide for photocatalytic synthesis of N-substituted derivatives
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Recently, photocatalysis has attracted considerable interest, leading to opportunities for using renewable energy sources. A Cu:Ni metal-organic framework (MOF) modified with graphene oxide (GO) was fabricated by a facile and convenient process. Subsequen
- Yusuf, Mohammad,Hira, Shamim Ahmed,Lim, Hyeonhan,Song, Sehwan,Park, Sungkyun,Park, Kang Hyun
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p. 9018 - 9027
(2021/04/16)
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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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- Tuning the Copper(II)/Copper(I) Redox Potential for More Robust Copper-Catalyzed C–N Bond Forming Reactions
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Complexes of copper and 1,10-phenanthroline have been utilized for organic transformations over the last 50 years. In many cases these systems are impacted by reaction conditions and perform best under an inert atmosphere. Here we explore the role the 1,1
- Biswas, Saborni,Cope, James D.,Emerson, Joseph P.,Goel, Ekta,Hall, Ruby S.,Hendrich, Michael P.,Riley, Kathleen M.,Stokes, Sean L.,Valle, Henry U.,Wipf, David O.
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supporting information
(2020/03/23)
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- Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone
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The reaction of (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium-chloride (HLCl) with copper(II) perchlorate led to mononuclear [CuLCl]ClO4 complex (1). The same reaction with excess of sodium azide gives di
- Milenkovi?, Milica R.,Papastavrou, Argyro T.,Radanovi?, Du?anka,Pevec, Andrej,Jagli?i?, Zvonko,Zlatar, Matija,Gruden, Maja,Vougioukalakis, Georgios C.,Turel, Iztok,An?elkovi?, Katarina,?obelji?, Bo?idar
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- Cu2O/1-(2-methylhydrazine-1-carbonyl)-isoquinoline 2-oxide catalyzed C-N cross-coupling reaction in aqueous media
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An experimentally simple, efficient, and inexpensive catalyst system was developed for the N-arylation of imidazole, indole, pyrrole, alkyl alcohol amines, and alkyl amines with aryl iodides and bromides. The reaction proceeds in water-ethanol media at 120 °C for 12 h with Cu2O as the catalyst, 1-(2-methylhydrazine-1-carbonyl)-isoquinoline 2-oxide (L2) as the ligand, NaOH as the base to generate a wide range of N-arylated products in moderate to excellent yields. Aqueous medium, ease of operation, and broad substrate scope give the process a benign environmental profile.
- Xie, Jian-Wei,Yao, Zhen-Bin,Wang, Xiao-Chuang,Zhang, Jie
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p. 3788 - 3792
(2019/06/08)
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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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- Functional 1,8-naphthyridine copper(I) complex as efficient catalyst for n-arylation of imidazoles coupling reactions
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The functional 1,8-naphthyridine copper(I) complex, synthesized through a non-catalyst C(sp3)-H methylenation, catalyzes the cross-coupling reaction of aryl halides with imidazoles, by C?N bond formation. The Cu(I) complex catalyzes the reaction with a low catalyst loading (1%, molar fraction) and cheap base even under aerobic conditions. The procedure tolerates aryl halides with various functional groups (such as methyl, methoxy, acetyl, fluoro, nitrile and nitro groups) and gives the corresponding coupling products in moderate to high yields.
- Gou, Gao-Zhang,Wu, Na,Zhang, Ju-Cheng,Shi, Ling,Liu, Gui-Yang,Liu, Wei,Mang, Chao-Yong,Chi, Shao-Ming
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p. 181 - 185
(2018/02/28)
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- A waste-minimized protocol for copper-catalyzed Ullmann-type reaction in a biomass derived furfuryl alcohol/water azeotrope
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We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines. Furfuryl alcohol (FA) can be mixed with water to form the corresponding azeotrope (20 wt% of FA) and therefore can be easily recovered and reused. This protocol is efficiently applied to substrates with various electronic nature and affords the expected products (27 examples) in generally good to excellent yields. It has also been demonstrated that the protocol is both chemically and environmentally effective as the azeotropic mixture can be easily and almost quantitatively recovered at the end of the process.
- Ferlin, Francesco,Trombettoni, Valeria,Luciani, Lorenzo,Fusi, Soliver,Piermatti, Oriana,Santoro, Stefano,Vaccaro, Luigi
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supporting information
p. 1634 - 1639
(2018/04/12)
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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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- 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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- Electrocatalytic Reduction of CO2 to CO with Re-Pyridyl-NHCs: Proton Source Influence on Rates and Product Selectivities
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A series of four electron-deficient-substituted Re(I) pyridyl N-heterocyclic carbene (pyNHC) complexes have been synthesized, and their electrocatalytic reduction of CO2 has been evaluated by cyclic voltammetry and controlled potential electrol
- Liyanage, Nalaka P.,Dulaney, Hunter A.,Huckaba, Aron J.,Jurss, Jonah W.,Delcamp, Jared H.
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p. 6085 - 6094
(2016/07/06)
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- Combined experimental/theoretical study of D-glucosamine promoted Ullmann-type C-N coupling catalyzed by copper(I): Does amino really count?
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Ullmann type C-N coupling reaction catalyzed by copper(I) with D-glucosamine derivatives as promoters was studied by means of combined experimental/theoretical investigation. The catalytic role of D-glucosamine was addressed. In contrast with previous speculations, the amino group may not count in the catalytic cycle in which the oxidative addition/reductive elimination mechanism works. Experimental results are in good agreement with theoretical findings. Extensive work indicates the wide applicability of the C-N coupling strategy exploited in this work.
- Ge, Xin,Chen, Xinzhi,Qian, Chao,Zhou, Shaodong
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p. 29638 - 29645
(2018/06/04)
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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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- Phosphorescent compound and Organic light emitting diode device using the same
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The present invention provides a phosphorescent compound represented by chemical formula. In the chemical formula, R1 to R15 are respectively and individually selected from hydrogen, deuterium (D), halogen such as F, Cl, and Br, CF3, a cyano group, a C1 t
- -
-
Paragraph 0120-0124
(2016/10/08)
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- Methylene bridging 1,8-naphthyridine ligand and copper (I) complex, preparing method and application
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The invention discloses a methylene bridging 1,8-naphthyridine ligand and copper (I) complex, a preparing method and an application. The molecular formula of the methylene bridging 1,8-naphthyridine ligand and copper (I) complex is shown in the specificat
- -
-
Paragraph 0062; 0063; 0064; 0065; 0066; 0067; 0068; 0069
(2017/04/26)
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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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- 2-halogenoimidazolium salt catalyzed aza-diels-alder reaction through halogen-bond formation
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2-Halogenoimidazolium salts are found to catalyze aza-Diels-Alder reaction of aldimines with Danishefsky diene in an efficient manner. Comparative studies and titration experiments support the formation of halogen bonding between imines and catalysts.
- Takeda, Youhei,Hisakuni, Daichi,Lin, Chun-Hsuan,Minakata, Satoshi
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supporting information
p. 318 - 321
(2015/01/30)
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- N -heterocyclic carbenes: Versatile second cyclometalated ligands for neutral iridium(III) heteroleptic complexes
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With 2-(2,4-difluorophenyl)pyridine (dfppy) as the first cyclometalated ligand and different monoanionic N-heterocyclic carbenes (NHCs) as the second cyclometalated ligands, 16 blue or greenish-blue neutral iridium(III) phosphorescent complexes, (dfppy)s
- Li, Tian-Yi,Liang, Xiao,Zhou, Liang,Wu, Chen,Zhang, Song,Liu, Xuan,Lu, Guang-Zhao,Xue, Li-Sha,Zheng, You-Xuan,Zuo, Jing-Lin
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p. 161 - 173
(2015/03/03)
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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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- An efficient d-glucosamine-based copper catalyst for C-X couplings and its application in the synthesis of nilotinib intermediate
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d-Glucosamine has been studied for C-N and C-S bond formations via cross-coupling reactions of nitrogen and sulfur nucleophiles with both aryl iodides and bromides. Imidazoles, benzimidazole, indole, pyrrolidine and diphenyl disulfide undergo reactions with aryl halides in the presence of 10 mol% d-glucosamine, 10 mol% CuI, and 2 equiv. of Cs2CO3 in DMSO-H2O at moderate temperature to give the corresponding products in good to excellent yields. Substrates bearing halides, free amino groups, trifluoromethyl and heterocycles were well tolerated. The high water solubility of the ligand enables easy catalyst removal. In addition, the application of this catalytic system for the synthesis of nilotinib intermediate was also successfully demonstrated using commercially available substrates. This journal is
- Wen, Ming,Shen, Chao,Wang, Linfang,Zhang, Pengfei,Jin, Jianzhong
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p. 1522 - 1528
(2015/02/18)
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- Energy Transfer in a Hybrid IrIII Carbene-PtII Acetylide Assembly for Efficient Hydrogen Production
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A new heterometallic supramolecular complex, consisting of an iridium carbene-based unit appended to a platinum terpyridine acetylide unit, representing a new IrIII-PtII structural motif, was designed and developed to act as an activ
- Yu, Zhen-Tao,Yuan, Yong-Jun,Chen, Xin,Cai, Jian-Guang,Zou, Zhi-Gang
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supporting information
p. 10003 - 10007
(2015/07/07)
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- Magnetically retrievable lepidocrocite supported copper oxide nanocatalyst (Fe-CuO) for N-arylation of imidazole
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A simple and efficient lepidocrocite-supported copper oxide catalyst (Fe-CuO) has been successfully prepared by a simple precipitation method in aqueous medium from readily available inexpensive starting materials and was used as a heterogeneous nanocatal
- Sivakami,Babu, S. Ganesh,Dhanuskodi,Karvembu
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p. 8571 - 8578
(2015/03/03)
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- Nano copper(i) oxide/zinc oxide catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides and arylboronic acids in air
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The synergistic effect of zinc and copper in Cu2O/ZnO nanoflake as a heterogeneous catalyst for the N-arylation of heterocycles with aryl halides and arylboronic acids in the absence of additional ligand in air were demonstrated. The catalyst was characterized by powder X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), BET surface area measurement, and FT-IR spectroscopy. The Royal Society of Chemistry 2014.
- Hosseini-Sarvari, Mona,Moeini, Fatemeh
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p. 7321 - 7329
(2014/02/14)
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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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- 8-Hydroxyquinoline functionalized peg-1000 bridged Dicationic ionic liquid as a novel Ligand for copper-catalyzed n-Arylation of Imidazoles
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A novel 8-hydroxyquinoline functionalized PEG-1000 bridged dicationic ionic liquid ([HQ-PEG1000- DIL][BF4]) was synthesized and characterized. It was applied as an efficiently recyclable ligand for copper- catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides. The catalytic system could be easily recovered and reused for at least five runs without obvious loss of catalytic activity.
- Wang, Ying-Lei,Luo, Jun,Liu, Zu-Liang
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p. 1007 - 1013
(2013/10/22)
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- A simple and efficient copper(II) complex as a catalyst for N-arylation of imidazoles
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Four inexpensive and air-/moisture-stable pyrrolecarbaldiminato-Cu complexes 1-4 were synthesized and evaluated to be a novel class of catalysts for the N-arylation of imidazoles with aryl halides. A variety of aryl iodides, bromides and activated aryl chlorides underwent the coupling with imidazoles, promoted by the catalyst 4, in moderate to good yields without the protection by an inert gas. Copyright
- Jiao, Yanli,Yan, Nannan,Xie, Jianwei,Ma, Xiaowei,Liu, Ping,Dai, Bin
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p. 267 - 270
(2013/08/24)
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- Luminescent biscarbene iridium(iii) complexes as living cell imaging reagents
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Five iridium(iii) complexes with two N-heterocyclic carbene (NHC) ligands and an ancillary ligand have been designed and successfully synthesized. With multicolor photoluminescence and low toxicity, these carbene complexes were tested, for the first time,
- Zhou, Yuyang,Jia, Junli,Li, Wanfei,Fei, Hao,Zhou, Ming
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supporting information
p. 3230 - 3232
(2013/05/08)
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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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- 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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- 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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- Efficient and reusable catalytic system of Cul-PEG for n-arylation of imidazoles
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A simple, efficient, and recyclable catalytic system of CuI-poly(ethylene glycol) (PEG) was developed for the N-arylation of imidazoles with aryl halides to afford corresponding N-arylimidazoles in good to excellent yields under mild conditions and free of any additional ligands and solvents. The isolation of the products was readily performed by simple extraction with ether, and the catalytic system could be reused without remarkable loss of activity even after six runs.
- Zhang, Qiang,Luo, Jun,Wei, Yunyang
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experimental part
p. 114 - 121
(2011/11/01)
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- Novel binuclear palladium(II) complexes of 2-oxoquinoline-3-carbaldehyde Schiff bases: Synthesis, structure and catalytic applications
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A series of novel binuclear Pd(II) complexes of the type [(PPh 3)2ClPd(L)PdCl] [where L = dianionic bridged ligands derived from 2-oxo-1,2-dihydroquinoline-3-carbaldehyde or its derivatives with o-aminophenol/o-aminothiophenol] have been reported. The new complexes have been characterized by elemental analysis, FT-IR, UV-Vis and NMR (1H and 31P) spectroscopic techniques. The coordination mode of the ligands and the geometry of the complexes were confirmed by single crystal X-ray crystallography of one of the complexes. The catalytic efficiency of one of the binuclear Pd(II) complexes was tested for N-arylation of imidazole.
- Priyarega, Sivakumar,Senthil Raja, Duraisamy,Ganesh Babu, Sundaram,Karvembu, Ramasamy,Hashimoto, Takeshi,Endo, Akira,Natarajan, Karuppannan
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experimental part
p. 143 - 148
(2012/04/11)
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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 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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- Use of acylhydrazine- and acylhydrazone-type ligands to promote CuI-catalyzed C-N cross-coupling reactions of aryl bromides with N-heterocycles
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A series of ten acylhydrazine- and acylhydrazone-type ligands were designed and synthesized. Their electronic and steric properties were easily modified and tuned by varying the substituents in the vicinity of the acylhydrazine and acylhydrazone units. The effect of ligands on the catalytic activity of Ullmann reactions was assessed by using a combination of these ligands with CuI. The catalytic system is very efficient for the C-N coupling reaction of azoles with aryl and heteroaryl bromides. A simple and efficient procedure for copper-catalyzed C-N cross-coupling reactions between aryl bromides and NH-containingheterocycles is illustrated. Readily available acylhydrazine- and acylhydrazone-typeligands promote the reaction.
- Li, Liuyi,Zhu, Lei,Chen, Dagui,Hu, Xuelei,Wang, Ruihu
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experimental part
p. 2692 - 2696
(2011/06/25)
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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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- 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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- 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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- A new, efficient and recyclable lanthanum(III) oxide-catalyzed C-N cross-coupling
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A new and efficient protocol for the C-N cross-coupling of aryl halides with heteroaromatic amines in the presence of lanthanum(III) oxide (10 mol%) as a recyclable catalyst, N,N′-dimethylethylenediamine (DMEDA) (20 mol%) and potassium hydroxide (KOH) as a base in dimethyl sulfoxide (DMSO) at 110 °C has been developed. This inexpensive catalytic system is highly effective towards the amination of aryl halides with various nitrogen nucleophiles and is significantly tolerant towards other functional groups in the substrates. Copyright
- Murthy, S. Narayana,Madhav,Reddy, V. Prakash,Nageswar
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supporting information; experimental part
p. 3241 - 3245
(2011/02/23)
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- Oxazolidin-2-one as efficient ligand for the copper-catalyzed N- Arylation of pyrrole, imidazole and indole
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Oxazolidin-2-one was found to be a facile ligand for the N-arylation of pyrrole, indole, and imidazole with aryl and heteroaryl iodides, bromides, and chlorides by applying Cul as catalyst. The easy preparation, commercial availability, lower molecular weight, and broad substrate applicability, as well as substituent compatibility of this catalysis system render oxazolidin-2-one great advantages over the Cu-catalyzed methods that have already been utilized in a number of applications.
- Ma, Hengchang,Wu, Shang,Sun, Qiangsheng,Lei, Ziqiang
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experimental part
p. 212 - 218
(2011/07/07)
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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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- 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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- Pyridine N-oxides as ligands in Cu-catalyzed Af-arylation of imidazoles in water
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N-Arylation of imidazoles with aryl halides catalyzed by a combination of copper(II) sulfate and 1,2-bis(2-pyridyl)-ethane-N,N′-dioxide in water afforded up to 95% yield.
- Liang, Lei,Li, Zhengkai,Zhou, Xiangge
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supporting information; experimental part
p. 3294 - 3297
(2009/11/30)
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- A simple and efficient catalytic system for N-arylation of imidazoles in water
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A study was conducted to develop a simple and efficient catalytic system for N-arylation of immidazoles in water. Demonstrations revealed that the catalytic system contained a number of significant advantages. Some of these advantages included the use of water as a green solvent in place of volatile organic solvents and the catalysis was performed without an inert gas atmosphere and with low catalyst loading. Investigations revealed that the presence of catalyst and PTC were essential for the catalysis reaction. The scope of aryl halide substrates was investigated by using the catalytic system under the optimized reaction conditions. It was also demonstrated that the catalytic system tolerated a variety of functionalized aryl halides in the reaction, including nitrile, nitro, acetyl, and ether groups. The new catalytic system was applied to a variety of imidazole derivatives to expand the scope of the methodology.
- Wang, Yi,Wu, Zhiqing,Wang, Lixia,Li, Zhengkai,Zhou, Xiangge
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supporting information; experimental part
p. 8971 - 8974
(2010/04/05)
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- CuI nanoparticles for C-N and C-O cross coupling of heterocyclic amines and phenols with chlorobenzenes
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(Chemical Equation Presented) Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A variety of products including N-arylimidazoles and aryl ethers were synthesized in good to excellent yields. 2009 American Chemical Society.
- Sreedhar,Arundhathi,Reddy, P. Linga,Kantam, M. Lakshmi
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supporting information; experimental part
p. 7951 - 7954
(2010/01/16)
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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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- Bis(μ-iodo)bis((-)-sparteine)dicopper(I): versatile catalyst for direct N-arylation of diverse nitrogen heterocycles with haloarenes
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The easy-to-prepare dimeric bis(μ-iodo)bis((-)-sparteine)dicopper(I) complex is shown to be a versatile catalyst for N-arylation of number of NH-heterocycles with structurally divergent aryl halides including activated aryl chloride substrates under mild conditions. The DFT studies not only provide structural insights into square-pyramidal Cu(III) intermediate complexes derived from (-)-sparteine, but also highlight the important role of sterically demanding (-)-sparteine ligand framework in promoting activation of aryl-chlorine bonds for N-arylation of imidazoles.
- Maheswaran,Krishna, G. Gopi,Prasanth, K. Leon,Srinivas,Chaitanya, G. Krishna,Bhanuprakash
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p. 2471 - 2479
(2008/09/18)
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- Copper(I) thiophene-2-carboxylate (CuTC): A versatile non-nitrogen ligand-based catalyst for direct N-arylation of imidazole and pyrazole using aryl iodides, aryl bromides, and aryl chlorides
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A new protocol to prepare N-aryl heterocyclic adducts in excellent yields via cross-coupling of HN-heterocycles with aryl halides is reported using commercially available and easy-to-prepare copper(I) thiophene-2-carboxylate (CuTC) as catalyst.
- Maheswaran, Hariharasarma,Krishna, Gaddamanugu Gopi,Srinivas, Vandanapu,Prasanth, Kurushunkal Leon,Rajasekhar, Chinamukthevi Venkata
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supporting information; experimental part
p. 515 - 517
(2009/04/10)
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