- A porous metal-organic framework as active catalyst for multiple C-N/C-C bond formation reactions
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A 3D porous metal-organic framework {[Cu(4-tba)2](solvent)}n (1·S) is assembled via 4-(1H-1,2,4-triazol-1-yl)benzoic acid (Htba) and Cu(II) nodes, which shows the [2 + 2] roto-translational interpenetrating network. Interestingly, 1 displays high CO2 adsorption selectivity over CH4/H2/O2/Ar/N2 gases, and acts an efficient catalyst precursor in some C-N/C-C bond formation reactions, including Chan-Lam coupling reaction of phenylboronic acid with imidazole, Suzuki-Miyoura coupling reaction of phenylboronic acids with aryl halides, and Heck coupling reaction of styrene with aryl halides.
- Wang, Bin,Yang, Pei,Ge, Zhi-Wei,Li, Cheng-Peng
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- Polymer supported copper(II) amine-imine complexes in the C-N and A3 coupling reactions
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New polymer supported Cu(II) complexes based on an epoxy functionalized gel type resin were prepared using the multi-stage procedures. The reactions of epoxy groups with ethylenediamine or tris(2-aminoethyl)amine, and then NH2 groups with salic
- Bukowska, Agnieszka,Bukowski, Wiktor,Bester, Karol,Hus, Krzysztof
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- Base-free anaerobic Cu(II) catalysed aryl-nitrogen bond formations
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The Cu(II) catalysed coupling of arylboronic acids with imidazole can be performed at ambient temperature without the need for base or dioxygen. The presence of water however is essential for the reaction to proceed.
- Van Berkel, Sander S.,Van Den Hoogenband, Adri,Terpstra, Jan Willem,Tromp, Moniek,Van Leeuwen, Piet W.N.M.,Van Strijdonck, Gino P.F.
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- Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water
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The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H2TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C–N coupling reactions of arylboronic acids and amines (Chan–Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan–Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.
- Venkateswarlu, Katta,Rao, Kanusu Umamaheswara
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- Bis(NHC)-Pd-catalyzed one-pot competitive C-C*C-C, C-C*C-O, C-C*C-N, and C-O*C-N cross-coupling reactions on an aryl di-halide catalyzed by a homogenous basic ionic liquid (TAIm[OH]) under base-free, ligand-free, and solvent-free conditions
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Bis(NHC)-Pd-catalyzed competitive asymmetrical C-C*C-C, C-C*C-O, C-C*C-N, and O-C*C-N cross-coupling reactions were performedviathe one-pot strategy in the presence of a new ionic liquid, which played the roles of solvent, base, and ligand simultaneously. The ionic liquid was prepared based on a methyl imidazolium moiety with hydroxyl counter anionsviaa Hofmann elimination on a 1,3,5-triazine framework (TAIm[OH]). Pd ions could be efficiently coordinated through the bis(NHC)-ligand moiety in the ionic liquid. Based on differences in the competitive kinetics of C-C cross-coupling reactions (Heck, Suzuki, and Sonogashira) with C-N and C-O cross-coupling reactions, and also differences in the kinetics of aryl halides, the coupling reactions could be selectively performed with a low amount of by-products. The competitive cross-coupling reactions were thus performed with high selectivity under mild reaction conditions.
- Zhu, Yanfang,Xu, Guiyang,Kazemnejadi, Milad
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p. 11662 - 11671
(2021/07/11)
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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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- 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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- 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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- NHC ligand-based half-sandwich iridium complexes: synthesis, structure and catalytic activity in acceptorless dehydrogenation and transfer hydrogenation
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A set of neutral C,C-chelate half-sandwich iridium(iii) complexes have been prepared with NHC ligands that contain pendant aromatic rings as potentially chelating donor sites. The catalytic activity of such iridium complexes has been investigated for the acceptorless dehydrogenation (AD) reactions of alcohols and for the transfer hydrogenation reactions of ketones. The prepared iridium(iii) complexes show excellent catalytic activity for AD reactions of a wide range of secondary alcohols, and they are also shown to be effective for the synthesis of aldehydes from primary alcohols without the observation of undesired byproducts such as esters. Additionally, these complexes are also highly efficient in transfer hydrogenation of ketones and aldehydes, which give the alcohols in good yields under mild conditions. The exact structure and bonding mode of the NHC-based iridium complexes was identified using various spectroscopic methods and single crystal X-ray analysis.
- Deng, Wei,Jin, Yan,Li, Rong-Jian,Liu, Zhen-Jiang,Wang, Yang,Yao, Zi-Jian
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p. 19002 - 19010
(2021/10/29)
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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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- 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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- Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions
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We have designed a functionalized metal-organic framework (MOF) of UiO topology as a support, with an extremely high surface area, adjustable pore sizes and stable crystalline coordination polymeric structure and implanted copper (Cu) nanoparticles thereon. The core three dimensional Zr-derived MOF (UiO-66-NH2) was modified with a biguanidine moiety following a covalent post-functionalization approach. The morphological and physicochemical features of the material were determined using analytical methods such as FT-IR, SEM, TEM, EDX, atomic mapping, XRD and ICP-OES. The SEM and XRD results justified the unaffected morphology of Zr-MOF after structural modifications. The as-synthesized UiO-66-biguanidine/Cu nanocomposite was catalytically explored in the aryl and heteroaryl Buchwald-Hartwig C-N and Ullmann type C-O cross coupling reactions with excellent yields. A library of biaryl amine and biaryl ethers was synthesized over the catalyst under mild and green conditions. Furthermore, the catalyst was isolated by centrifugation and recycled 11 times with no significant copper leaching or change in its activity.
- Veisi, Hojat,Neyestani, Narges,Pirhayati, Mozhgan,Ahany Kamangar, Sheida,Lotfi, Shahram,Tamoradi, Taiebeh,Karmakar, Bikash
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p. 22278 - 22286
(2021/07/02)
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- Immobilization of copper(II) into polyacrylonitrile fiber toward efficient and recyclable catalyst in Chan-Lam coupling reactions
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A series of polyacrylonitrile fiber (PANF)-supported copper(II) catalysts were prepared through the immobilization of Cu(II) into prolinamide-modified PANF (PANPA-2F) and subsequently used for the synthesis of diverse N-arylimidazoles from arylboronic acids and imidazole. The prepared Cu(II)@PANPA-2Fs were well characterized by mechanical strength, FT-IR, XRD, XPS and SEM. Among them, CuCl2@PANPA-2F exhibited excellent catalytic performance, and its activity was significantly affected by the Cu loading. This catalytic system also displayed good activity in the synthesis of N-arylsulfonamides from arylboronic acids and tosyl azide. It was highly efficient in gram-scale reactions and could be reused five times. The advantages of low cost, easy preparation, good durability and facile recovery make the fiber catalyst attractive.
- Zhang, Chenlu,Zhu, Hai,Gang, Kaiyue,Tao, Minli,Ma, Ning,Zhang, Wenqin
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- Cu(I)–N-heterocyclic carbene-catalyzed base free C–N bond formation of arylboronic acids with amines and azoles
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A new N-heterocyclic carbene (NHC) precursor of imidazolium chloride and its corresponding Cu(I)–NHC complex 1 was synthesized. The complex 1 was found to be a highly effective catalyst for Chan-Evans-Lam coupling of arylboronic acid with amines and azoles (including imidazole, pyrazole and triazole), without addition of base at room temperature. Various substituents on three substrates can be tolerated, giving the desired coupling products in good to excellent yields (62–94%). The method is practical and offers an alternative to the corresponding copper-catalyzed Chan-Evans-Lam process for the construction of C–N bonds.
- Zhang, Maoyuan,Xu, Zengbing,Shi, Dabin
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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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- Chitosan nanoparticles functionalized poly-2-hydroxyaniline supported CuO nanoparticles: An efficient heterogeneous and recyclable nanocatalyst for N-arylation of amines with phenylboronic acid at ambient temperature
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The present study aims to prepare an effective and eco-friendly nanocatalyst for the Chan–Lam coupling reaction of phenylboronic acid and amine in aerobic conditions. For this purpose, chitosan was extracted from shrimp shells waste by demineralization, deproteinization, and deacetylation processes and then converted to chitosan nanoparticles (CSN) by the ionic gelation with tripolyphosphate anions. Afterward, poly-2-hydroxyaniline (P2-HA) was grafted to chitosan nanoparticles (NPs) to employ as the support for CuO NPs. Characterization of the nanocatalyst was done using Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), mapping, energy-dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA). The CuO NPs were identified in the spherical shape with an average size of 17 nm. The prepared nanocatalyst exhibited excellent catalytic performance with a high turnover number (TON) and turnover frequency (TOF) for the Chan–Lam coupling reaction of phenyl boronic acid and amines with different electronic properties. The prepared catalyst could be readily recovered and reused for at least five runs without any noticeable change in structure and catalytic performance. Chitosan (CS) was prepared via demineralization, deproteinization, and deacetylation of shrimp shell and chitosan nanoparticles (CSN) were prepared via ionic gelation process. Polymerization of 2-HA on the CSN surface was done to increase functional groups and create active sites for CuO NPs attachments. CuO NPs-P2-HA-CSN nanocomposite has been shown high efficiently for the Chan–Lam coupling reaction.
- Seyedi, Neda,Zahedifar, Mahboobeh
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- Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions
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Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Herein, we report the implementation of substoichiometric quantities of redox mediators to address limitations to Cu-catalyzed electrosynthesis. Mechanistic studies reveal that mediators serve multiple roles by (i) rapidly oxidizing low-valent Cu intermediates, (ii) stripping Cu metal from the cathode to regenerate the catalyst and reveal the active Pt surface for proton reduction, and (iii) providing anodic overcharge protection to prevent substrate oxidation. This strategy is applied to Chan-Lam coupling of aryl-, heteroaryl-, and alkylamines with arylboronic acids in the absence of chemical oxidants. Couplings under these electrochemical conditions occur with higher yields and shorter reaction times than conventional reactions in air and provide complementary substrate reactivity.
- Walker, Benjamin R.,Manabe, Shuhei,Brusoe, Andrew T.,Sevov, Christo S.
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supporting information
p. 6257 - 6265
(2021/05/07)
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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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- Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity**
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Herein, we disclose that electrochemical stimulation induces new photocatalytic activity from a range of structurally diverse conventional photocatalysts. These studies uncover a new electron-primed photoredox catalyst capable of promoting the reductive cleavage of strong C(sp2)?N and C(sp2)?O bonds. We illustrate several examples of the synthetic utility of these deeply reducing but otherwise safe and mild catalytic conditions. Finally, we employ electrochemical current measurements to perform a reaction progress kinetic analysis. This technique reveals that the improved activity of this new system is a consequence of an enhanced catalyst stability profile.
- Chernowsky, Colleen P.,Chmiel, Alyah F.,Wickens, Zachary K.
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p. 21418 - 21425
(2021/08/25)
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- One-step synthesis of imidazoles from Asmic (anisylsulfanylmethyl isocyanide)
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Substituted imidazoles are readily prepared by condensing the versatile isocyanide Asmic, anisylsulfanylmethylisocyanide, with nitrogenous π-electrophiles. Deprotonating Asmic with lithium hexamethyldisilazide effectively generates a potent nucleophile that efficiently intercepts nitrile and imine electrophiles to afford imidazoles. In situ cyclization to the imidazole is promoted by the conjugate acid, hexamethyldisilazane, which facilitates the requisite series of proton transfers. The rapid formation of imidazoles and the interchange of the anisylsulfanyl for hydrogen with Raney nickel make the method a valuable route to mono- and disubstituted imidazoles.
- AlWedi, Embarek,Chao, Allen,Fleming, Fraser F.,Mueller, Louis G.
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p. 1499 - 1502
(2021/07/02)
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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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- Green tea extract–modified silica gel decorated with palladium nanoparticles as a heterogeneous and recyclable nanocatalyst for Buchwald-Hartwig C–N cross-coupling reactions
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A novel green tea extract–encapsulated silica gel decorated with in situ–generated Pd nanoparticles is reported as an efficient, green heterogeneous catalyst in the Buchwald-Hartwig C–N cross-coupling reaction. It was characterized by several analytical techniques. Thereafter, a wide range of aryl amines were synthesized in good to excellent yields by reaction of different substituted aryl halides and secondary amines over the catalyst. The material is sufficiently stable and could be used at least six times in a model Buchwald-Hartwig reaction without noticeable change in its catalytic activity. Heterogeneity of the catalyst was examined by a hot filtration test.
- Veisi, Hojat,Tamoradi, Taiebeh,Karmakar, Bikash,Hemmati, Saba
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- Cu(I)-anchored polyvinyl alcohol coated-magnetic nanoparticles as heterogeneous nanocatalyst in Ullmann-type C–N coupling reactions
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In this paper, the preparation of a novel magnetic nanocatalyst (Fe3O4?PVA/CuCl) is described, which involves coating of polyvinyl alcohol (PVA) onto the surface of Fe3O4 nanoparticles and its subsequent coordination with CuCl catalyst. The nanocatalyst was characterized by various analytical methods, including Fourier-transform infrared, X-ray diffraction, inductively coupled plasma spectroscopy, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy, vibrating-sample magnetometry, and EDX elemental mapping. Moreover, the nanocatalyst was efficiently used in the N-arylation of amines via the formation of a carbon–nitrogen bond between the aryl halides and amines by Ullmann-type coupling reactions. The catalyst was sufficiently stable and can be reused for at least seven times in a model Ullmann reaction without remarkable alteration in its catalytic behavior. Heterogeneity of the catalyst was investigated by a hot filtration test.
- Ahany Kamangar, Sheida,Hashemi Salehi, Mirmehdi,Hekmati, Malak,Hemmati, Saba,Yousefi, Mohammad
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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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- Intercalation of copper salt to montmorillonite K-10 and its application as a reusable catalyst for Chan–Lam cross-coupling reaction
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A simple and efficient catalytic system has been developed by adsorption of copper salt in the interlayers of montmorillonite K-10. The catalytic system impressively exercises the green chemistry perspective leading to effortless recovery and recyclabilit
- Sarmah, Manashi,Dewan, Anindita,Boruah, Purna K.,Das, Manash R.,Bora, Utpal
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- 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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- Synthesis and Characterization of a Tetradentate, N-Heterocyclic Carbene Copper(II) Complex and Its Use as a Chan-Evans-Lam Coupling Catalyst
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Copper N-heterocyclic carbenes (NHCs) are an emerging area of focus for catalysis and other applications. Using a straightforward methodology, a new and highly modifiable tetradentate copper(II) NHC complex was generated and characterized using X-ray crystallography, UV-vis and EPR spectroscopy, cyclic voltammetry, and ESI-MS. This copper(II) NHC complex adopted a distorted 4-coordinate coordination mode and demonstrates a unique absorption spectrum for a copper(II) species, but more interestingly, its redox properties indicate that it can readily access all three common copper oxidation states under atmospheric conditions. The tetradentate copper(II) NHC complex was used to catalytically generate new C-N bonds from a series of phenylboronic acids and amines. Once this CEL methodology was refined, moderate to high yields were achieved using catalytic amounts of the copper(II) complex to couple phenylboronic acids to a series of aniline derivatives. Substituted phenylboronic acids and anilines had minimal impact on the catalytic capabilities of this copper complex; however, there is some indication that steric interactions between catalyst and substrates may have an impact on efficient catalysis. The straightforward synthesis of this framework and the utilization of an inexpensive, first-row transition metal center in this system highlight the usefulness of copper(II) NHCs as catalyst for cross-coupling reactions.
- Cope, James D.,Sheridan, Patrick E.,Galloway, Christopher J.,Awoyemi, Raymond Femi,Stokes, Sean L.,Emerson, Joseph P.
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p. 4457 - 4464
(2021/01/09)
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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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- 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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- Efficient nickel(II) immobilized on EDTA‐modified Fe3O4?SiO2 nanospheres as a novel nanocatalyst for amination of heteroaryl carbamates and sulfamates through the cleavage of C-O bond
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In this report, there was immobilized Nickel(II) on EDTA‐modified Fe3O4?SiO2 nanospheres and catalytic activity of which was described in the arylation reaction of nitrogen nucleophiles via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates. This protocol was applied to various nitrogen nucleophiles such as amines, anilines and N-heterocyclic compounds (pyrroles, indoles and imidazoles) in good to excellent yields. This reaction was promoted without the use of any external ligands under simple and mild conditions. The synthesized catalyst was well characterized by FT‐IR, XRD, TEM, FE-SEM, TGA, DLS,XPS, VSM, EDX, ICP and nitrogen adsorption-desorption isotherm analysis. The recycling studies revealed that the catalyst could be easily recovered by used the external magnetic field and directly reused for at least 7 times without the significant decrease in its catalytic activity.
- Dindarloo Inaloo, Iman,Eslahi, Hassan,Esmaeilpour, Mohsen,Majnooni, Sahar
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- Metabolically stable diphenylamine derivatives suppress androgen receptor and BET protein in prostate cancer
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Androgen receptor (AR) is a crucial driver of prostate cancer (PC). AR-relevant resistance remains a major challenge in castration-resistant prostate cancer (CRPC). Bromodomain and extra-terminal domain (BET) family are critical AR coregulators. Here, we
- Chen, Yuanwei,Deng, Yufang,Du, Wu,Li, Xinghai,Xu, Ruixue,Yan, Guoyi,Yu, Jiang,Zhou, Peiting
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- Preparation method of diarylamine compound
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The invention relates to a preparation method of a diarylamine compound. Specifically, under the catalysis of cuprous oxide supported by chitosan, the arylation reaction used for a nitrogen-containingheterocyclic compound is achieved, and the corresponding diarylamine compound is obtained. The preparation method of the diarylamine compound has the advantages that the process conditions are simple, the yield is good, the operability is strong, and the functional group tolerance is wide.
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Paragraph 0070; 0071; 0072
(2019/04/26)
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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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- α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles
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The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C-N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-Arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.
- Yuan, Chunling,Zhao, Yingdai,Zheng, Li
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p. 2173 - 2180
(2019/11/25)
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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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- 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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- L -(-) -Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles
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l-(-)-Quebrachitol (QCT) has been found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.
- Zhou, Qifan,Du, Fangyu,Chen, Yuanguang,Fu, Yang,Sun, Wenjiao,Wu, Ying,Chen, Guoliang
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p. 8160 - 8167
(2019/06/28)
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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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- Synergistic catalysis for light-driven proton reduction using a polyoxometalate-based Cu-Ni heterometallic-organic framework
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Synergistic effects of bimetallic Ni and Cu supported on metal-organic polymer composites based on Wells-Dawson P2W18O626- clusters as photosensitizer units were identified, and we report a novel approach for addressing these issues for dehydrogenation and hydrogen production reactions.
- Sun, Wenlong,He, Cheng,Liu, Tao,Duan, Chunying
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supporting information
p. 3805 - 3808
(2019/04/01)
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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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- URJC-1-MOF as New Heterogeneous Recyclable Catalyst for C-Heteroatom Coupling Reactions
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Guillermo Calleja and co-workers from @urjc describe URJC-1-MOF as a new heterogeneous recyclable catalyst for c-heteroatom coupling reactions. The capacity of copper-based URJC-1-MOF as a MOF catalyst in cross-coupling reactions has been evaluated, focusing on the Chan-Lam-Evans arylation-type reactions on amines and alcohols without extra additives or ligands. The extraordinary chemical and structural stability of URJC-1-MOF and its good specific surface, make this material a promising alternative to homogeneous Cu (II) catalysts for cross-coupling reactions. URJC-1-MOF showed a remarkable catalytic activity for cross-coupling C?N and C?O reactions, higher than other heterogeneous and homogeneous copper-based catalyst, such as CuO, HKUST-1, Cu?MOF-74, Cu(OAc)2 and CuSO4?5H2O. Moreover, its easy recovery by simple filtration and reusability in successive runs without any loss of activity and stability, demonstrates the potential of URJC-1-MOF as an alternative catalyst for this kind of reactions in different chemical media of industrial interest.
- Mu?oz, Antonio,Leo, Pedro,Orcajo, Gisela,Martínez, Fernando,Calleja, Guillermo
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p. 3376 - 3380
(2019/07/04)
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- Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids—New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers
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For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,
- Pavlov, Dmitry,Sukhikh, Taisiya,Filatov, Evgeny,Potapov, Andrei
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- Efficient N-arylation of azole compounds utilizing selective aryl-transfer TMP-iodonium(III) reagents
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It was determined that diaryliodonium(III) triflates bearing a trimethoxybenzene (TMP) auxiliary are more reactive than the reported selective aryl-transfer iodonium salts in the N-arylation of benzimidazoles and other types of azole compounds under catalytic conditions. The TMP-iodonium(III) salts can thus effectively facilitate the reaction at 50 °C or below, producing the corresponding N-arylated biaryls without the formation of TMP-derived coupling byproducts. Utilization of this TMP reagent under mild conditions would prevent the underlying problem of participation of the auxiliary group in the coupling reactions, which is observed while using the iodonium(III) salts that require elevated temperatures.
- Koseki, Daichi,Aoto, Erika,Shoji, Toshitaka,Watanabe, Kazuma,In, Yasuko,Kita, Yasuyuki,Dohi, Toshifumi
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p. 1281 - 1286
(2019/04/10)
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- Palladium catalyzed hydrodefluorination of fluoro-(hetero)arenes
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Palladium catalyzed hydrodefluorination was developed for fine-tuning the properties of fluoro-(hetero)aromatic compounds. The robust reaction can be set up in air, requires only commercially available components, and tolerates a variety of heterocycles and functionalities relevant to drug discovery. Given the prevalence of fluorine incorporation around metabolic hotspots, the corresponding deuterodefluorination reaction may prove useful for converting fluorinated libraries to deuterated analogues to suppress the oxidative metabolism by kinetic isotope effects.
- Gair, Joseph J.,Grey, Ronald L.,Giroux, Simon,Brodney, Michael A.
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supporting information
p. 2482 - 2487
(2019/04/10)
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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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- 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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- 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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- 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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- Palladium(II) anchored on polydopamine coated-magnetic nanoparticles (Fe3O4&at;PDA&at;Pd(II)): A heterogeneous and core–shell nanocatalyst in Buchwald–Hartwig C–N cross coupling reactions
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An efficient method was proposed to synthesize polydopamine (PDA)-coated Fe3O4 nanoparticles (Fe3O4&at;PDA). For the first time, effective deposition of Pd complex is explained by using Fe3O4&at;PDA as a core–shell magnetic coordinator and stabilizer agent. In this method, palladium ions were adsorbed on Fe3O4&at;PDA surfaces through immersion of the Fe3O4&at;PDA into a palladium plating bath. The structure, morphology and physicochemical features of the prepared particles were studied using various analytical methods including high resolution transmission electron microscopy (HR-TEM), field emission scanning electron microscope (FESEM), energy-dispersive X-ray spectroscopy (EDS), vibrating sample magnetometer (VSM), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma (ICP), thermogravimetric analysis (TGA) and FT-IR spectroscopy. Core–shell Fe3O4&at;PDA/Pd(II) nanoparticles showed excellent catalytic performance as a reusable nanocatalyst in Pd-catalyzed Buchwald–Hartwig C–N cross coupling reaction. A variety of aryl amines were prepared through reaction of aryl halides (chloride, bromide and iodide) and amines in high yields. The catalyst can be recycled and reapplied up to six cycles with no considerable change in its catalytic activity.
- Hemmati, Saba,Sarachegol, Pegah,Veisi, Hojat
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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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- 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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- A PEG/copper(i) halide cluster as an eco-friendly catalytic system for C-N bond formation
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The catalytic activities of eight copper(i) halide clusters assembled from copper(i) halide and ferrocenyltelluroethers, 1-8, were investigated in C-N formation under various conditions. A catalytic procedure using poly(ethylene glycol) (PEG-400) as a gre
- Li, Cheng-An,Ji, Wei,Qu, Jian,Jing, Su,Gao, Fei,Zhu, Dun-Ru
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p. 7463 - 7470
(2018/06/15)
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