- 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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Read Online
- New, simple, and effective thiosemicarbazide ligand for copper(II)-catalyzed N-arylation of imidazoles
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A new methodology of copper-catalyzed coupling reaction has been developed, involving imidazoles react with aryl halides using CuCl2 ·H2O as catalyst and 1-(4- hydroxy-3-me thoxybenzylidene) thiosemicarbazide (L1) as ligand. It is th
- Shan, Yuefeng,Wang, Ying,Jia, Xiaolei,Cai, Wenwen,Xiang, Jiannan
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Read Online
- Functionalization of superparamagnetic Fe3O4@SiO2 nanoparticles with a Cu(II) binuclear Schiff base complex as an efficient and reusable nanomagnetic catalyst for N-arylation of α-amino acids and nitrogen-containing heterocycles with aryl halides
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Fe3O4@SiO2 nanoparticles was functionalized with a binuclear Schiff base Cu(II)-complex (Fe3O4@SiO2/Schiff base-Cu(II) NPs) and used as an effective magnetic hetereogeneous nanocatalyst for the N-arylation of α-amino acids and nitrogen-containig heterocycles. The catalyst, Fe3O4@SiO2/Schiff base-Cu(II) NPs, was characterized by Fourier transform infrared (FTIR) and ultraviolet-visible (UV-vis) analyses step by step. Size, morphology, and size distribution of the nanocatalyst were studied by transmission electron microscopy (TEM), scanning electron microscopy (SEM), and dynamic light scatterings (DLS) analyses, respectively. The structure of Fe3O4 nanoparticles was checked by X-ray diffraction (XRD) technique. Furthermore, the magnetic properties of the nanocatalyst were investigated by vibrating sample magnetometer (VSM) analysis. Loading content as well as leaching amounts of copper supported by the catalyst was measured by inductive coupled plasma (ICP) analysis. Also, thermal studies of the nanocatalyst was studied by thermal gravimetric analysis (TGA) instrument. X-ray photoelectron spectroscopy (XPS) analysis of the catalyst revealed that the copper sites are in +2 oxidation state. The Fe3O4@SiO2/Schiff base-Cu(II) complex was found to be an effective catalyst for C–N cross-coupling reactions, which high to excellent yields were achieved for α-amino acids as well as N-hetereocyclic compounds. Easy recoverability of the catalyst by an external magnet, reusability up to eight runs without significant loss of activity, and its well stability during the reaction are among the other highlights of this catalyst.
- Sardarian,Kazemnejadi,Esmaeilpour
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- A novel two-dimensional metal-organic framework as a recyclable heterogeneous catalyst for the dehydrogenative oxidation of alcohol and theN-arylation of azole compounds
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A novel metal-organic framework (MOF) with two-dimensional (2D) crystal structure was developed using Cu(NO3)2·3H2O and 2,2′,5,5′-tetramethoxy-[1,1′-biphenyl]-4,4′-dicarboxylic acid. Further, its structure was characterized using infrared spectroscopy, thermogravimetry, X-ray diffraction, and X-ray crystallography. The activated Cu-MOF was used to catalyze the dehydrogenative oxidation of alcohol andN-arylation of azole compounds. Furthermore, it could be easily recovered and reused.
- Liu, Chengxin,Cui, Jin,Wang, Yufang,Zhang, Mingjie
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p. 11739 - 11744
(2021/03/31)
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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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- 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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- Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions
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A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.
- Farrokhi, Alireza,Rouzifar, Majid,Sansano, José Miguel,Sobhani, Sara
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p. 19963 - 19976
(2021/11/12)
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- Axial Ligand Coordination Tuning of the Electrocatalytic Activity of Iron Porphyrin Electrografted onto Carbon Nanotubes for the Oxygen Reduction Reaction
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The oxygen reduction reaction (ORR) is essential in many life processes and energy conversion systems. It is desirable to design transition metal molecular catalysts inspired by enzymatic oxygen activation/reduction processes as an alternative to noble-metal-Pt-based ORR electrocatalysts, especially in view point of fuel cell commercialization. We have fabricated bio-inspired molecular catalysts electrografted onto multiwalled carbon nanotubes (MWCNTs) in which 5,10,15,20-tetra(pentafluorophenyl) iron porphyrin (iron porphyrin FeF20TPP) is coordinated with covalently electrografted axial ligands varying from thiophene to imidazole on the MWCNTs’ surface. The catalysts’ electrocatalytic activity varied with the axial coordination environment (i. e., S-thiophene, N-imidazole, and O-carboxylate); the imidazole-coordinated catalyst MWCNTs-Im-FeF20TPP exhibited the highest ORR activity among the prepared catalysts. When MWCNT-Im-FeF20TPP was loaded onto the cathode of a zinc?air battery, an open-cell voltage (OCV) of 1.35 V and a maximum power density (Pmax) of 110 mW cm?2 were achieved; this was higher than those of MWCNTs-Thi-FeF20TPP (OCV=1.30 V, Pmax=100 mW cm?2) and MWCNTs-Ox-FeF20TPP (OCV=1.28 V, Pmax=86 mW cm?2) and comparable with a commercial Pt/C catalyst (OCV=1.45 V, Pmax=120 mW cm?2) under similar experimental conditions. This study provides a time-saving method to prepare covalently immobilized molecular electrocatalysts on carbon-based materials with structure–performance correlation that is also applicable to the design of other electrografted catalysts for energy conversion.
- Zhou, Xin-You,Xu, Chao,Guo, Peng-Peng,Sun, Wei-Li,Wei, Ping-Jie,Liu, Jin-Gang
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supporting information
p. 9898 - 9904
(2021/05/29)
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- Tunable aryl imidazolium ionic liquids (TAIILs) as environmentally benign catalysts for the esterification of fatty acids to biodiesel fuel
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Herein, we describe the synthesis of tunable aryl imidazolium ionic liquid catalysts and tested for esterification of fatty acids to biodiesel. In this work, six tunable aryl imidazolium ionic liquids (TAIILs) 1a-1f were prepared. These ionic liquids were used as the economical and reusable catalysts for the synthesis of biodiesel fuels. The reaction has been preceded in a monophase at 80 °C for 4 h, after which the product was separated from the catalyst system by a simple liquid/liquid phase separation at room temperature with excellent yields. With the simple post-process, the catalyst is reusable at least 6 times. This novel method offers a short reaction time, good yields, and environmentally benign characteristics.
- Ho, Wen-Yueh,Lin, Wesley,Lin, Yi-Jyun,Luo, Shun-Yuan,Pantawane, Amit,Su, Po-Fang,Thul, Mayur,Tseng, Shao-An,Wu, Hsin-Ru
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- NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media
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The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is
- Alavi G., Seyyedeh Ameneh,Nasseri, Mohammad Ali,Kazemnejadi, Milad,Allahresani, Ali,Hussainzadeh, Mahdi
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p. 7741 - 7757
(2021/05/13)
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- A post-synthetically modified metal-organic framework for copper catalyzed denitrative C-N coupling of nitroarenes under heterogeneous conditions
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Here we report, for the first time, the Ullmann C-N coupling reaction of nitroarenes which is achieved by using a copper containing metal-organic framework (MOF) catalyst under heterogenous conditions. The ready availability of nitroarenes and their low cost have made them ideal replacements for haloarenes as electrophilic coupling partners. Notably, the reaction protocol suppresses the by-product formation in the catalytic reaction. The catalyst has been designed and synthesized by two step post-synthesis functionalization of a MOF,viz.dabco MOF-1 with a -NH2functional group (DMOF-NH2). In the post-synthetic treatment, salicylaldehyde has been used for organic modification first and then copper(ii) was successfully incorporated onto the inner surface of the porous material. The hybrid porous solid thus obtained has been employed in the catalytic C-N coupling reaction of nitroarenes with a wide variety of amines under heterogeneous conditions, which displayed very high turnover frequencies (TOF) in catalytic reactions attesting its efficacy towards theN-arylation reaction.
- Maity, Tanmoy,Ghosh, Pameli,Das, Soma,Saha, Debraj,Koner, Subratanath
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p. 5568 - 5575
(2021/04/06)
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- INHIBITING UBIQUITIN SPECIFIC PEPTIDASE 9X
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The disclosure provides novel chemical compounds useful as inhibitors of ubiquitin specific peptidase 9X (USP9X). USP9X inhibiting compounds are useful in the treatment of disease and disorders associated with modulation of USP9X, such as cancer.
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Paragraph 0073-0074; 0091
(2020/07/15)
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- 2-pyridine substituted urea structural small molecule compounds as well as synthesis and application thereof
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The invention relates to 2-pyridine substituted urea structural small molecule compounds as well as synthesis and application thereof. Specifically, the invention discloses the compounds represented by a formula (I) shown in the specification, enantiomers, diastereomers, racemates or a mixture of the compounds, or a pharmaceutically acceptable salt, hydrate and solvate of the compounds, a preparation method of the above materials, and applications of the above materials in preparation of an ASK1 small molecule inhibitor, or medicines for preventing and/or treating diseases related to ASK1, especially liver diseases, lung diseases, cardiovascular diseases, kidney diseases and metabolic diseases.
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Paragraph 0197; 0455-0457
(2020/03/03)
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- N-Heterocyclic Carbene Copper(I) Complex Catalyzed Coupling of (Hetero)aryl Chlorides and Nitrogen Heterocycles: Highly Efficient Catalytic System
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A highly efficient catalytic system for the N-arylation reactions of (hetero)aryl chlorides and nitrogen heterocycles with a copper(I) complex containing a 1,10-phenanthroline analogue N-heterocyclic carbene (NHC) has been reported. The complex was characterized by 1H NMR and 13C NMR spectroscopy and elemental analysis, and its structure was determined by single-crystal X-ray diffraction. The NHC-copper(I) complex was employed as pre-catalyst for Ullmann type N-arylation reactions of (hetero)aryl chlorides with various azoles. A variety of hindered and functionalized azoles and (hetero)aryl chlorides were transformed in good to excellent yields.
- Zhang, Mengyao,Zhang, Yingying,Zhang, Huixin,Zeng, Yongfei,Liu, Guiyan
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p. 1252 - 1256
(2020/08/05)
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- Integrating CuO?Fe2O3 Nanocomposites and Supramolecular Assemblies of Phenazine for Visible-Light Photoredox Catalysis
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A photoredox catalytic ensemble consisting of CuO-Fe2O3 nanocomposites and oligomeric derivative of phenazine has been developed. The prepared system acts as an efficient photoredox catalyst for C?N bond formation reaction via SET mechanism under ‘green’ conditions (aerial environment, mixed aqueous media, recyclable), requiring less equivalents of base and amine substrate. The present study demonstrates the significant role of supramolecular assemblies as photooxidants and reductants upon irradiation and their important contribution towards the activation of the metallic centre through energy transfer and electron transfer pathways. The potential of oligomer 4: CuO-Fe2O3 has also been explored for C?C bond formation reactions via the Sonogashira protocol.
- Kaur, Lovjot,Deol, Harnimarta,Kumar, Manoj,Bhalla, Vandana
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supporting information
p. 892 - 898
(2020/03/04)
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- A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water
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A novel magnetically recyclable bimetallic catalyst was prepared by anchoring imidazolium moiety and PEG chains on Fe3O4 NPs and named as Fe3O4?PEG/Cu-Co. It was found to be a powerful catalyst for the Sonogashira, Suzuki, and C-N cross-coupling reactions in water as a green solvent without the need for any external base. Fe3O4?PEG/Cu-Co was well characterized with FT-IR, FE-SEM, TEM, VSM, EDX, ICP, UV-visible, CV, and XPS analyses. Optimum ranges of parameters such as time, temperature, and amount of catalyst were investigated by Design-Expert 10.0.7 software for C-C Suzuki, Sonogashira, and C-N cross-coupling reactions to find the optimum conditions. The catalyst was compatible with a variety of aryl halides and N-arenes and gave favorable coupling products with good to high yields for all of them. Hot filtration and Hg poisoning tests involving the nanocatalyst revealed the stability, low metal leaching, and heterogeneous nature of the catalyst. Reaction mechanisms were proposed by study of the UV-visible spectra in situ as well as hydroquinone tests during the progress of reactions. In situ XPS analysis was also used to study the reaction mechanism. To prove the synergistic performance of Co and Cu in the catalyst, its various homologues were synthesized and applied to a model reaction separately, and then their catalytic activities were investigated. Finally, the catalyst could be recovered from the reaction mixture simply, and reused for several cycles with a minimum loss in catalytic activity and performance.
- Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat
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p. 10645 - 10660
(2020/09/18)
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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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- 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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- 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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- Schiff base fluorescent compound and synthesis method thereof, and method for fluorescently detecting zinc ions
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The invention discloses a Schiff base fluorescent compound and a synthesis method thereof, and a method for fluorescently detecting zinc ions. The Schiff base fluorescent compound is as shown in the specification. The synthesis method for the Schiff base
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Paragraph 0049-0053
(2019/01/24)
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- High-performance sono/nano-catalytic system: CTSN/Fe3O4-Cu nanocomposite, a promising heterogeneous catalyst for the synthesis of: N -arylimidazoles
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Herein, a promising heterogeneous nanoscale catalytic system constructed of chitosan (CTSN, as a polymeric basis), iron oxide nanoparticles (Fe3O4 NPs, as the magnetic agent), and copper oxide nanoparticles (CuO NPs, as the main cata
- Taheri-Ledari, Reza,Hashemi, Seyed Masoud,Maleki, Ali
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p. 40348 - 40356
(2019/12/25)
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- Ligand complex of copper (II) supported on superparamagnetic Fe3O4?SiO2 nanoparticles: an efficient and magnetically separable catalyst for N-arylation of nitrogen-containing heterocycles with aryl halides
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In this study, we introduce the ligand complex of copper (II) supported on superparamagnetic Fe3O4?SiO2 nanoparticles as a highly intriguing magnetic catalyst in N-arylation of nitrogen heterocycles with aryl halides. The present methodology offers several advantages such as; low catalyst loading, the use of magnetically recoverable and reusable catalyst, high to excellent yields without using any external ligands or additives, short reaction times and simplicity of operation. Also, the magnetic catalyst could be easily separated from the final product by an external magnet and reused up to seven times without any significant loss of activity. Therefore, this separation strategy with negligible leaching makes Fe3O4?SiO2/ligand/Cu(II) an economical catalyst to perform this transformation.
- Zahmatkesh, Saeed,Esmaeilpour, Mohsen,Mollaiy Poli, Azade
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p. 323 - 334
(2019/11/05)
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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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- 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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- Synthesis, Characterization, and Molecular Docking Study of Some Novel Imidazole Derivatives as Potential Antifungal Agents
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The azole pharmacophore is still regarded as a viable lead structure for the synthesis of more effective antifungal agents. In this study, two novel series of imidazole derivatives containing dithiocarbamate (5a–5g) and (benz)azolethiol (6a–6n) side chains that are structurally related to the famous antifungal azole pharmacophore were synthesized, and the structures of them were characterized by spectral (IR, 1H NMR, 13C NMR, and MS spectra) analyses. The synthesized compounds were screened in vitro antifungal activity against pathogenic strains fungi. Theoretical ADME (absorption, distribution, metabolism, and excretion) predictions were calculated for final compounds. A molecular docking study of the most active compound with target “lanosterol 14α-demethylase” (CYP51) was performed to unravel the mode of antifungal action. Compound 5e, which features imidazole and 4-methoxybenzyl piperazine scaffolds, showed the most promising antifungal activity with an MIC50 value of 0.78?μg/mL against C. krusei. Effect of the compound 5e against ergosterol biosynthesis was observed by LC–MS–MS method, which is based on quantification of ergosterol level in C.?krusei.
- I??k, Ay?en,Acar ?evik, Ulviye,Sa?l?k, Begüm Nurpelin,?zkay, Yusuf
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p. 142 - 152
(2019/01/04)
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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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- Fragment-Based Discovery of a Qualified Hit Targeting the Latency-Associated Nuclear Antigen of the Oncogenic Kaposi's Sarcoma-Associated Herpesvirus/Human Herpesvirus 8
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The latency-associated nuclear antigen (LANA) is required for latent replication and persistence of Kaposi's sarcoma-associated herpesvirus/human herpesvirus 8. It acts via replicating and tethering the virus episome to the host chromatin and exerts other functions. We conceived a new approach for the discovery of antiviral drugs to inhibit the interaction between LANA and the viral genome. We applied a biophysical screening cascade and identified the first LANA binders from small, structurally diverse compound libraries. Starting from a fragment-sized scaffold, we generated optimized hits via fragment growing using a dedicated fluorescence-polarization-based assay as the structure-activity-relationship driver. We improved compound potency to the double-digit micromolar range. Importantly, we qualified the resulting hit through orthogonal methods employing EMSA, STD-NMR, and MST methodologies. This optimized hit provides an ideal starting point for subsequent hit-to-lead campaigns providing evident target-binding, suitable ligand efficiencies, and favorable physicochemical properties.
- Kirsch, Philine,Jakob, Valentin,Oberhausen, Kevin,Stein, Saskia C.,Cucarro, Ivano,Schulz, Thomas F.,Empting, Martin
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supporting information
(2019/05/01)
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- Fragment-Based Discovery of a Qualified Hit Targeting the Latency-Associated Nuclear Antigen of the Oncogenic Kaposi's Sarcoma-Associated Herpesvirus/Human Herpesvirus 8
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The latency-associated nuclear antigen (LANA) is required for latent replication and persistence of Kaposi's sarcoma-associated herpesvirus/human herpesvirus 8. It acts via replicating and tethering the virus episome to the host chromatin and exerts other functions. We conceived a new approach for the discovery of antiviral drugs to inhibit the interaction between LANA and the viral genome. We applied a biophysical screening cascade and identified the first LANA binders from small, structurally diverse compound libraries. Starting from a fragment-sized scaffold, we generated optimized hits via fragment growing using a dedicated fluorescence-polarization-based assay as the structure-activity-relationship driver. We improved compound potency to the double-digit micromolar range. Importantly, we qualified the resulting hit through orthogonal methods employing EMSA, STD-NMR, and MST methodologies. This optimized hit provides an ideal starting point for subsequent hit-to-lead campaigns providing evident target-binding, suitable ligand efficiencies, and favorable physicochemical properties.
- Kirsch, Philine,Jakob, Valentin,Oberhausen, Kevin,Stein, Saskia C.,Cucarro, Ivano,Schulz, Thomas F.,Empting, Martin
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supporting information
p. 3924 - 3939
(2019/05/06)
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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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- A designed bi-functional sugar-based surfactant: Micellar catalysis for C-X coupling reaction in water
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A bi-functional sugar-based surfactant ALA14 was designed as the ligand and micelle constructor and demonstrated to promote the copper-catalyzed C-X coupling reaction in water. The nature of this micelle, formed by sugar-based surfactants, was investigated with CMC, DLS, and TEM, by which encapsulation and aggregation of the substrates in micelles were verified. Additionally, it was addressed by 1H-NMR analysis that the enrichment position of the substrates is in the lipophilic alkyl chain. Finally, moderate to excellent yields of the aimed products were obtained in this work. This remarkably simple strategy expanded the scope of C-X coupling reaction in water; most notably, both water and ALA14 can be recycled and reused.
- Ge, Xin,Zhang, Shihui,Chen, Xinzhi,Liu, Xuemin,Qian, Chao
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supporting information
p. 2771 - 2776
(2019/06/13)
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- Highly active bidentate N-heterocyclic carbene/ruthenium complexes performing dehydrogenative coupling of alcohols and hydroxides in open air
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Eight bidentate NHC/Ru complexes, namely [Ru]-1-[Ru]-8, were designed and prepared. In particular, [Ru]-2 displayed extraordinary performance even in open air for the dehydrogenative coupling of alcohols and hydroxides. Notably, an unprecedentedly low catalyst loading of 250 ppm and the highest TON of 32 800 and TOF of 3200 until now were obtained.
- Wang, Zhi-Qin,Tang, Xiao-Sheng,Yang, Zhao-Qi,Yu, Bao-Yi,Wang, Hua-Jing,Sang, Wei,Yuan, Ye,Chen, Cheng,Verpoort, Francis
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supporting information
p. 8591 - 8594
(2019/07/25)
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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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- 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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- 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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- 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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- 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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- Ultrafine hybrid Cu2O-Fe2O3 nanoparticles stabilized by hexaphenylbenzene-based supramolecular assemblies: A photocatalytic system for the Ullmann-Goldberg coupling reaction
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Ultrafine hybrid Cu2O-Fe2O3 NPs have been prepared using the supramolecular assemblies of hexaphenylbenzene (HPB) derivative 3 as nanoreactors and stabilizers. The as-prepared hybrid Cu2O-Fe2O3 NPs serve as an efficient and recyclable photocatalytic system for carrying out C-N coupling between aryl halides and various amines (aliphatic, aromatic and N-heterocyclic) at room temperature in mixed aqueous media under visible light irradiation. Amazingly, Cu2O-Fe2O3 NPs also exhibited high efficiency in the reactions involving the synthesis of biologically important N-substituted carbazole derivatives. The work being presented in this article demonstrates the preparation of a 'dip strip' coated with the as-prepared catalytic system and utilization of this paper strip as a recyclable and portable heterocatalytic system for carrying out the Ullmann-Goldberg coupling.
- Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
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p. 5346 - 5357
(2018/12/05)
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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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- 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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- Coordination compound containing 1,10-phenanthroline-shaped N-heterocyclic carbene copper (I), and application thereof
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The invention discloses a coordination compound containing 1,10-phenanthroline-shaped N-heterocyclic carbene copper (I) (as well as a coordinate compound monocrystal), and application thereof. The coordination compound containing the 1,10-phenanthroline-s
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Paragraph 0014
(2018/07/30)
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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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- 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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- Cu2O/Cs2CO3/DMF: An efficient catalytic system for N-arylation of imidazole with aryl halides under ligand-free conditions
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A ligand-free Cu-catalyzed protocol for the Ullmann-type N-arylation of N-containing heterocycles with aryl or heteroaryl iodides and bromides has been established. A broad range of functional groups is well tolerated on both of the cross-coupling partners, producing the desired products in good to excellent yields.
- Wang, Xiaochuang,Wang, Meiji,Xie, Jianwei
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supporting information
p. 1797 - 1803
(2017/09/22)
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- Copper immobilized on magnetite nanoparticles coated with ascorbic acid: An efficient and reusable catalyst for C─N and C─O cross-coupling reactions
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In a continuation of using magnetic nanoparticle (MNP)-supported catalysts, ascorbic acid (readily available, very safe and with strong affinity to MNPs) was used instead of the commonly used silica layer coating. This hybrid was used for immobilizing copper nanoparticles to produce Cu/ascorbic acid@MNPs catalyst. The catalyst was characterized and used in carbon–oxygen and carbon–nitrogen (various substrates) cross-coupling reactions in aqueous media and at room temperature with excellent product yields. Furthermore, the catalyst could be quickly and completely recovered using an external magnetic field and reused for six reaction cycles without significant change in catalytic activity.
- Hajipour, Abdol R.,Check, Maryam,Khorsandi, Zahra
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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 0141; 0142; 0143; 0144; 0145; 0146
(2017/10/05)
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- CopperII phthalocyanine as an efficient and reusable catalyst for the N-arylation of nitrogen containing heterocycles
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Copper phthalocyanine (CuIIPc) was found to be an efficient catalyst for the catalyzed N-arylation of N–H heterocycles with aryl iodides and bromides under mild reaction conditions. A variety of hindered and functionalized N–H heterocycles and aryl halides were successfully used as the substrates for the given catalytic reaction and were transformed in good to excellent yields.
- Yadav, Kumar Karitkey,Narang, Uma,Bhattacharya, Soumee,Chauhan, Shive M.S.
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supporting information
p. 3044 - 3048
(2017/07/17)
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- Copper(I) Oxide/N,N′-Bis[(2-furyl)methyl]oxalamide-Catalyzed Coupling of (Hetero)aryl Halides and Nitrogen Heterocycles at Low Catalytic Loading
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An easily prepared oxalic diamide is a powerful ligand for the copper-catalyzed coupling of aryl halides with nitrogen heterocycles. Only 1–2 mol% each of copper(I) oxide and N,N′-bis[(2-furyl)methyl]oxalamide (BFMO) are needed to form N-arylation products under mild conditions. More than 10 different types of nitrogen heterocycles are compatible with these conditions, thereby giving the corresponding N-arylation products. (Figure presented.).
- Pawar, Govind Goroba,Wu, Haibo,De, Subhadip,Ma, Dawei
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supporting information
p. 1631 - 1636
(2017/05/22)
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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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- Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction
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A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.
- Zhang, Xiao,Lu, Guo-Ping,Cai, Chun
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p. 5580 - 5585
(2016/10/21)
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- Synthesis and biological evaluation of azole-diphenylpyrimidine derivatives (AzDPPYs) as potent T790M mutant form of epidermal growth factor receptor inhibitors
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A series of novel azole-diphenylpyrimidine derivatives (AzDPPYs) were synthesized and biologically evaluated as potent EGFRT790Minhibitors. Among these analogues, the most active inhibitor 6e not only displayed high activity against EGFRT790M/L858Rkinase (IC50?=?3.3?nM), but also was able to repress the replication of H1975 cells harboring EGFRT790Mmutation at a concentration of 0.118?μmol/L. In contrast to the lead compound rociletinib, 6e slightly reduces the key EGFRT790M-minduced drug resistance. Significantly, inhibitor 6e demonstrates high selectivity (SI?=?299.3) for T790M-containing EGFR mutants over wild type EGFR, hinting that it will cause less side effects.
- Song, Zhendong,Jin, Yue,Ge, Yang,Wang, Changyuan,Zhang, Jianbin,Tang, Zeyao,Peng, Jinyong,Liu, Kexin,Li, Yanxia,Ma, Xiaodong
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p. 5505 - 5512
(2016/10/24)
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- Heterogeneous sequential N-arylation of N-heterocycles over copper anchored mesoporous silica catalyst
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N-Arylation reaction of N-heterocyclic compounds has been carried out in excellent yield using copper anchored SBA-15 catalyst. Sequential N-arylation reactions employing single catalyst under heterogeneous condition provides a straightforward access to a
- Das, Soma,Maity, Tanmoy,Koner, Subratanath
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- Cu2O/nano-CuFe2O4: An efficient and magnetically recoverable catalyst for the ligand-free N-arylation of amines and nitrogen heterocycles with aryl halides
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An efficient strategy has been developed for the N-arylation of azoles and aliphatic amines with aryl halide using a Cu2O/nano-CuFe2O4 magnetic composite as the catalyst and KOH as the base. The methodology is found to be applicable to a variety of nitrogen-containing heterocycles, such as imidazole, indole, and pyrrole, as well as aliphatic amines in high yields with practical simplicity under cost-effective "ligand-free" conditions. The magnetic property of the catalyst allowed its fast separation from the reaction medium by an external magnet. Additionally, the inexpensive catalyst could be recycled for five consecutive runs with small drops in catalytic activity.
- Elhampour, Ali,Nemati, Firouzeh,Kaveh, Mahdieh
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supporting information
p. 223 - 225
(2016/03/01)
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