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Cas Database

10040-95-6

10040-95-6

Identification

  • Product Name:1H-Imidazole,1-(4-methoxyphenyl)-

  • CAS Number: 10040-95-6

  • EINECS:

  • Molecular Weight:174.202

  • Molecular Formula: C10H10N2O

  • HS Code:2933290090

  • Mol File:10040-95-6.mol

Synonyms:Imidazole,1-(p-methoxyphenyl)- (7CI,8CI);1-(4-Methoxyphenyl)-1H-imidazole;1-(4-Methoxyphenyl)imidazole;1-(p-Methoxyphenyl)imidazole;N-(4-Methoxyphenyl)imidazole;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:1-(4-Methoxyphenyl)imidazole
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:1-(4-Methoxyphenyl)imidazole 98%
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:1-(4-Methoxyphenyl)imidazole 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-(4-Methoxyphenyl)-1H-imidazole 98%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1-(4-Methoxyphenyl)imidazole 98%
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  • Product Description:1-(4-Methoxyphenyl)imidazole 98%
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  • Manufacture/Brand:Crysdot
  • Product Description:1-(4-Methoxyphenyl)-1H-imidazole 98%
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  • Manufacture/Brand:Chemenu
  • Product Description:1-(4-Methoxyphenyl)imidazole 98%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:1-(4-METHOXYPHENYL)IMIDAZOLE 95.00%
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  • Manufacture/Brand:American Custom Chemicals Corporation
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Relevant articles and documentsAll total 196 Articles be found

Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles

Zhang, Hui,Cai, Qian,Ma, Dawei

, p. 5164 - 5173 (2005)

CuI-catalyzed coupling reaction of electron-deficient aryl iodides with aliphatic primary amines occurs at 40 °C under the promotion of N-methylglycine. Using L-proline as the promoter, coupling reaction of aryl iodides or aryl bromides with aliphatic primary amines, aliphatic cyclic secondary amines, or electron-rich primary arylamines proceeds at 60-90 °C; an intramolecular coupling reaction between aryl chloride and primary amine moieties gives indoline at 70 °C; coupling reaction of aryl iodides with indole, pyrrole, carbazole, imidazole, or pyrazole can be carried out at 75-90 °C; and coupling reaction of electron-deficient aryl bromides with imidazole or pyrazole occurs at 60-90 °C to provide the corresponding N-aryl products in good to excellent yields. In addition, N,N-dimethylglycine promotes the coupling reaction of electron-rich aryl bromides with imidazole or pyrazole to afford the corresponding N-aryl imidazoles or pyrazoles at 110 °C. The possible action of amino acids in these coupling reactions is discussed.

Magnetic nanoparticle-supported proline as a recyclable and recoverable ligand for the CuI catalyzed arylation of nitrogen nucleophiles

Chouhan, Gagan,Wang, Dashan,Alper, Howard

, p. 4809 - 4811 (2007)

Magnetic nanoparticle-supported proline ligand was prepared and used for the CuI catalyzed Ullmann-type coupling reactions of aryl/heteroaryl bromides with various nitrogen heterocycles to form the corresponding N-aryl products in good to excellent yields

Tuning the Copper(II)/Copper(I) Redox Potential for More Robust Copper-Catalyzed C–N Bond Forming Reactions

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.

, (2020)

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

Unique copper-salen complex: An efficient catalyst for N-arylations of anilines and imidazoles at room temperature

Gogoi, Ankur,Sarmah, Gayatri,Dewan, Anindita,Bora, Utpal

, p. 31 - 35 (2014)

We have reported here the catalytic activity of a unique Cu-salen type complex in N-arylation of anilines with arylboronic acids in water. The protocol is found to be applicable for a wide range of electronically diversified arylboronic acids and anilines with excellent yields of the isolated product. Further the scope of this protocol has been extended to the synthesis of various N-aryl imidazoles in iso-propanol.

Two-dimensional copper-based metal-organic framework as a robust heterogeneous catalyst for the N-arylation of imidazole with arylboronic acids

Li, Zhao-Hao,Xue, Li-Ping,Wang, Lei,Zhang, Shuai-Tao,Zhao, Bang-Tun

, p. 119 - 121 (2013)

N-arylation of imidazole was accomplished with a two-dimensional (2D) [Cu(ima)2]n metal-organic framework in methanol at room temperature. A variety of N-arylimidazoles were isolated in good yields after a short reaction time. Moreov

Recyclable hydrophobic copper (II) phthalocyanine catalyzed N-arylation of imidazoles in dimethylsulfoxide

Huang, Qiang,Zhou, Limei,Jiang, Xiaohui,Qi, Xiaolong,Wang, Zhonghua,Lang, Wencheng

, p. 1818 - 1824 (2014)

Copper (II) phthalocyanine (CuPc) was used as a catalyst for the N-arylation of imidazoles with aryl iodides or bromides. The catalyst showed high activity and could be reused 3 times without any significant loss in activity. The catalyst was characterized by Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and ultraviolet-visible spectroscopy.

Synthesis, structure and stability of new PtII-bis(N- heterocyclic carbene) complexes

Ahrens, Sebastian,Herdtweck, Eberhardt,Goutal, Sigrid,Strassner, Thomas

, p. 1268 - 1274 (2006)

The use of metal acetates has allowed the synthesis of NHC complexes without isolation of the free carbene. This route is very useful in cases where the metal acetates are readily available and has been used, for example, for the synthesis of bis(N-hetero

Highly efficient copper-catalyzed formation of N-aryl diazoles using KF/A12O3

Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Alikarami, Mohammad

, p. 2124 - 2126 (2006)

A simple and efficient method for the coupling of aryl iodides with heterocyclic compounds such as diazoles that does not require the use of alkoxide bases is described. The C-N bond forming procedure shows that the combination of air stable CuI and 1,10-phenanthroline in the presence of KF/Al2O3 comprises an extremely efficient and general catalyst system for the N-arylation of aryl iodides. Different functionalized aryl iodides were coupled with diazoles using this method. Georg Thieme Verlag Stuttgart.

Synergistic catalysis for light-driven proton reduction using a polyoxometalate-based Cu-Ni heterometallic-organic framework

Sun, Wenlong,He, Cheng,Liu, Tao,Duan, Chunying

, p. 3805 - 3808 (2019)

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.

Copper immobilized on magnetite nanoparticles coated with ascorbic acid: An efficient and reusable catalyst for C─N and C─O cross-coupling reactions

Hajipour, Abdol R.,Check, Maryam,Khorsandi, Zahra

, (2017)

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.

Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water

Inamoto, Kiyofumi,Nozawa, Kanako,Kadokawa, Jun,Kondo, Yoshinori

, p. 7794 - 7798 (2012)

Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-fr

Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions

Veisi, Hojat,Neyestani, Narges,Pirhayati, Mozhgan,Ahany Kamangar, Sheida,Lotfi, Shahram,Tamoradi, Taiebeh,Karmakar, Bikash

, p. 22278 - 22286 (2021)

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.

The [Cu(OH).TMEDA]2Cl2-catalyzed coupling of arylboronic acids with imidazoles in water.

Collman,Zhong,Zeng,Costanzo

, p. 1528 - 1531 (2001)

-

An efficient copper-catalyzed coupling of aryl halides with imidazoles

Kiyomori, Ayumu,Marcoux, Jean-Francois,Buchwald, Stephen L.

, p. 2657 - 2660 (1999)

Copper-catalyzed N-arylation of imidazoles can be accomplished using (CuOTf)2 · benzene as a copper source and Cs2CO3 as a base in xylenes at 110-125 °C. Addition of 1,10-phenanthroline (phen) and trans, trans- dibenzylide

L-Proline Promoted Ullmann-Type Coupling Reactions of Aryl Iodides with Indoles, Pyrroles, Imidazoles or Pyrazoles

Ma, Dawei,Cai, Qian

, p. 128 - 130 (2004)

The Ullmann-type coupling reactions of aryl iodides and several nitrogen heterocycles occur at 80-90°C with L-proline as additive, giving N-arylpyrroles, N-arylindoles, N-arylimidazoles, and N-pyrazoles in good to excellent yields.

CuI nanoparticles for C-N and C-O cross coupling of heterocyclic amines and phenols with chlorobenzenes

Sreedhar,Arundhathi,Reddy, P. Linga,Kantam, M. Lakshmi

, p. 7951 - 7954 (2009)

(Chemical Equation Presented) Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A variety of products including N-arylimidazoles and aryl ethers were synthesized in good to excellent yields. 2009 American Chemical Society.

Copper-catalyzed arylation of nitrogen heterocycles from anilines under ligand-free conditions

Toummini, Dounia,Tlili, Anis,Bergs, Julien,Ouazzani, Fouad,Taillefer, Marc

, p. 14619 - 14623 (2014)

The arylation of pyrazole and derivatives can be achieved by coupling arenediazonium species (formed in situ from anilines) by using a catalytic system that employs low-toxicity and inexpensive copper metal under very mild and ligand-free conditions (T = 20 ° C). From other nitrogen heterocycles, the presence of an additive (NBu4I) significantly improves the efficiency of the catalytic system. These results represent the first examples of C-N bond formation from arenediazonium species.

CopperII phthalocyanine as an efficient and reusable catalyst for the N-arylation of nitrogen containing heterocycles

Yadav, Kumar Karitkey,Narang, Uma,Bhattacharya, Soumee,Chauhan, Shive M.S.

, p. 3044 - 3048 (2017)

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.

Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone

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

, p. 22 - 30 (2019)

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

An efficient base-free N-arylation of imidazoles and amines with arylboronic acids using copper-exchanged fluorapatite

Kantam, M. Lakshmi,Venkanna, Gopaldasu T.,Sridhar, Chidara,Sreedhar, Bojja,Choudary, Boyapati M.

, p. 9522 - 9524 (2006)

(Chemical Equation Presented) N-Arylation of imidazoles and amines with arylboronic acids was accomplished with copper-exchanged fluorapatite (Cu-FAP) in methanol at room temperature. The products N-arylimidazoles and N-arylamines were isolated in good to excellent yields. A variety of arylboronic acids were converted to the corresponding N-arylimidazoles and N-arylamines, demonstrating the versatility of the reaction.

Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides

Cristau, Henri-Jean,Cellier, Pascal P.,Spindler, Jean-Francis,Taillefer, Marc

, p. 5607 - 5622 (2004)

Mild, efficient, copper-catalyzed N-arylation procedures for nitrogen heterocycles, amides, carbamates, and C-arylation procedures for malonic acid derivatives have been developed that afford high yields of arylated products with excellent selectivity. The N-arylation of imidazole with aryl bromides or iodides was found to be greatly accelerated by inexpensive, air-stable catalyst systems, combining catalytic copper salts or oxides with a set of structurally simple chelating ligands. The reaction was shown to be compatible with a broad range of aryl halides, encompassing sterically hindered, electron-poor, and electron-rich ones, providing the arylated products under particularly mild conditions (50-82°C). The lower limit in ligand and catalyst loading and the scope of Ullmann-type condensations catalyzed by complexes bearing those ligands with respect to the nucleophile class have also been investigated. Chelating Schiff base Chxn-Py-Al (1c) generates a remarkably general copper catalyst for N-arylation of pyrrole, indole, 1,2,4-triazole, amides, and carbamates; and C-arylation of diethyl malonate, ethyl cyanoacetate, and malononitrile with aryl iodides under mild conditions (50-82°C). The new method reported here is the most successful to date with regard to Ullmann-type arylation of some of these nucleophiles.

Intercalation of copper salt to montmorillonite K-10 and its application as a reusable catalyst for Chan–Lam cross-coupling reaction

Sarmah, Manashi,Dewan, Anindita,Boruah, Purna K.,Das, Manash R.,Bora, Utpal

, (2020)

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

A novel two-dimensional metal-organic framework as a recyclable heterogeneous catalyst for the dehydrogenative oxidation of alcohol and theN-arylation of azole compounds

Liu, Chengxin,Cui, Jin,Wang, Yufang,Zhang, Mingjie

, p. 11739 - 11744 (2021)

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.

A metal-organic framework Cu2(BDC)2(DABCO) as an efficient and reusable catalyst for Ullmann-type N-arylation of imidazoles

Nguyen, Tung T.,Phan, Nam T. S.

, p. 1877 - 1883 (2014)

A highly porous metal-organic framework (Cu2(BDC)2(DABCO)) was synthesized and used as an efficient and recyclable heterogeneous catalyst for the Ullmann-type N-arylation of aryl halides with imidazoles. The Cu2(BDC)2(DABCO) was characterized by several techniques, including X-ray powder diffraction, scanning electron microscopy, transmission electron microscopy, thermogravimetric analysis, Fourier transform infrared, atomic absorption spectrophotometry, and nitrogen physisorption measurements. The catalyst offered high activity under mild conditions, confirming outstanding advantages when employing the Cu2(BDC)2(DABCO) as catalyst for Ullmann-type N-arylation reaction. The catalyst could be separated from the reaction mixture by simple filtration, and could be reused without a significant degradation in catalytic activity.

An efficient polymer-supported copper(II) catalyst for the N-arylation reaction of N(H)-heterocycles with aryl halides as well as arylboronic acids

Islam, Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Salam, Noor,Paul, Sumantra,Hossain, Dildar,Mobarok, Manir

, p. 447 - 458 (2011)

Immobilization of copper onto polystyrene provided a polymer-supported copper(II) catalyst, which was effective in cross-coupling reactions between N-containing substrates and arylboronic acids using methanol as a solvent in air under base-free conditions

Iron oxide encapsulated by copper-Apatite: An efficient magnetic nanocatalyst for: N-Arylation of imidazole with boronic acid

Amadine, Othmane,Essamlali, Younes,Amedlous, Abdallah,Zahouily, Mohamed

, p. 36471 - 36478 (2019)

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

Copper fluorapatite catalyzed N-arylation of heterocycles with bromo and iodoarenes

Lakshmi Kantam,Venkanna,Sridhar,Shiva Kumar

, p. 3897 - 3899 (2006)

Copper exchanged fluorapatite (CuFAP) is an effective heterogeneous catalyst for N-arylation of heterocycles with bromo- or iodoarenes using K2CO3 as base. N-Arylated products were isolated in good to excellent yields, demonstrating the versatility of the reaction.

A highly versatile catalytic system for N-arylation of amines with aryl chlorides in water

Huang, Manna,Lin, Xiaoqin,Zhu, Xinhai,Peng, Weili,Xie, Jianwei,Wan, Yiqian

, p. 4523 - 4527 (2011)

The C-N coupling between nucleophiles and aryl chlorides, which are less expensive, less reactive, and more abundant than their bromide and iodide counterparts, is challenging but of great interest for industrial applications. An oxalyldihydrazide/hexane-2,5-dione (100-150 mol-%)/CuO system was found to enable the reaction of a wide range of nucleophiles with a variety of aryl chlorides in water for the first time.

Chan–Lam cross-coupling reactions promoted by anionic copper(I)/iodide species with cationic methyl-((pyridinyl)-pyrazolyl)pyridin-1-ium

Xue, Jiang-Yan,Li, Jun-Chi,Li, Hong-Xi,Li, Hai-Yan,Lang, Jian-Ping

, p. 7014 - 7020 (2016)

Four anionic ligands including 1-methyl-3(or 4)-(1-(pyridin-2-yl)-1H-pyrazol-3-yl)pyridin-1-ium iodide ([3,2′-pypzpym]I, [4,2′-pypzpym]I) and 1-methyl-3(or 4)-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)pyridin-1-ium iodide ([2,3′-pypzpym]I, [2,4′-pypzpym]I) are prepared. Reaction of CuI with [3,2′-pypzpym]I affords a mononuclear complex [CuI2(3,2′-pypzpym)] (1) and a one-dimensional coordination polymer [(Cu4I6)(3,2′-pypzpym)2]n(2). Analogous reactions of CuI with [4,2′-pypzpym]I, [2,3′-pypzpym]I or [2,4′-pypzpym]I yield [Cu4I6(4,2′-pypzpym)2] (3), [CuI2(2,3′-pypzpym)] (4) and [CuI2(2,4′-pypzpym)] (5), respectively. Relative to that of CuI, complexes 1–5 exhibit enhanced catalytic activities towards the Chan–Lam cross-coupling reactions of imidazole and arylboronic acids in a H2O[sbnd]MeCN (v/v=2:1). This catalytic system is involved in the C[sbnd]N cross-coupling reaction and works for a variety of imidazole derivatives as well as arylboronic acids with different electronic properties.

Efficient N-arylation catalyzed by a copper(I) pyrazolyl-nicotinic acid system

Liu, Hai-Yang,Yu, Zhen-Tao,Yuan, Yong-Jun,Yu, Tao,Zou, Zhi-Gang

, p. 9141 - 9144 (2010)

Catalyst 6-(1H-pyrazol-1-yl)nicotinic acid L-CuCl behaves as a very active promoter of the N-arylation reactions, as it has been demonstrated with varieties of substrates under mild reaction conditions. A Cu(I) complex based on L of precatalyst has been isolated by a hydrothermal method and structurally characterized.

Efficient and recyclable copper-based MOF-catalyzed N-arylation of N-containing heterocycles with aryliodides

Li, Zihao,Meng, Fei,Zhang, Jie,Xie, Jianwei,Dai, Bin

, p. 10861 - 10865 (2016)

Copper-based MOF-199 was used as an efficient heterogeneous catalyst to catalyze cross-coupling reactions between N-containing heterocycles and aryliodides with high yields. The catalyst can be easily separated from the reaction mixture, and can be reused at least 5 times without significantly decreasing the activity. The XRD results showed that the crystallinity and structure of MOF-199 can be maintained well during the coupling reaction.

An efficient d-glucosamine-based copper catalyst for C-X couplings and its application in the synthesis of nilotinib intermediate

Wen, Ming,Shen, Chao,Wang, Linfang,Zhang, Pengfei,Jin, Jianzhong

, p. 1522 - 1528 (2015)

d-Glucosamine has been studied for C-N and C-S bond formations via cross-coupling reactions of nitrogen and sulfur nucleophiles with both aryl iodides and bromides. Imidazoles, benzimidazole, indole, pyrrolidine and diphenyl disulfide undergo reactions with aryl halides in the presence of 10 mol% d-glucosamine, 10 mol% CuI, and 2 equiv. of Cs2CO3 in DMSO-H2O at moderate temperature to give the corresponding products in good to excellent yields. Substrates bearing halides, free amino groups, trifluoromethyl and heterocycles were well tolerated. The high water solubility of the ligand enables easy catalyst removal. In addition, the application of this catalytic system for the synthesis of nilotinib intermediate was also successfully demonstrated using commercially available substrates. This journal is

A reusable polymer supported copper(I) complex for the C-N bond cross-coupling reaction

Islam,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Mobarok, Manir

, p. 1352 - 1357 (2011)

The Ullmann coupling of amines with aryl iodide as well as arylboronic acids and N(H)-heterocycles with arylboronic acids has been carried out efficiently using PS-LCu(I) catalyst. The copper complex has been prepared and characterized by using scanning electron microscope (SEM), elemental analysis, atomic absorption spectroscopy (AAS), Thermo gravimetric analysis and spectrometric methods like Fourier transform infrared spectroscopy (FTIR). The effects of various parameters such as temperature, solvent and base on the reaction system were studied. The reusability experiments show that the catalyst can be used five times without much loss in the catalytic activity.

N-terminal strategy (N1-N4) toward high performance liquid crystal materials

Hong, Fengying,Xia, Zhengce,Zhu, Dezhao,Wu, Hongxiang,Liu, Jianhui,Zeng, Zhuo

, p. 1285 - 1292 (2016)

Liquid crystal materials have a variety of applications in many fields such as display techniques as well as photonics and optics. However, only few design principles have been disclosed on liquid crystal materials with different N-heterocycles as the terminal groups, which hinder the development of the heterocyclic liquid crystals. Here, a strategy of molecular design for N-heterocyclic liquid crystal materials is reported. On the basis of this strategy, a series of convenient N-heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,3,4-tetrazole were applied to synthesize the novel liquid crystals. Most of them have proved to exhibit good mesomorphic behaviors which make them excellent components in the mixture of the LCDs materials. The simple attachment of N-heterocyclic units to the liquid crystal molecules through a mild reaction condition will provide a good prospect for the design of N-heterocyclic liquid crystals.

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

Esmaeilpour, Mohsen,Sardarian, Ali Reza,Firouzabadi, Habib

, (2018)

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.

Oxazolidin-2-one as efficient ligand for the copper-catalyzed N- Arylation of pyrrole, imidazole and indole

Ma, Hengchang,Wu, Shang,Sun, Qiangsheng,Lei, Ziqiang

, p. 212 - 218 (2010)

Oxazolidin-2-one was found to be a facile ligand for the N-arylation of pyrrole, indole, and imidazole with aryl and heteroaryl iodides, bromides, and chlorides by applying Cul as catalyst. The easy preparation, commercial availability, lower molecular weight, and broad substrate applicability, as well as substituent compatibility of this catalysis system render oxazolidin-2-one great advantages over the Cu-catalyzed methods that have already been utilized in a number of applications.

A simple and efficient catalytic system for N-arylation of imidazoles in water

Wang, Yi,Wu, Zhiqing,Wang, Lixia,Li, Zhengkai,Zhou, Xiangge

, p. 8971 - 8974 (2009)

A study was conducted to develop a simple and efficient catalytic system for N-arylation of immidazoles in water. Demonstrations revealed that the catalytic system contained a number of significant advantages. Some of these advantages included the use of water as a green solvent in place of volatile organic solvents and the catalysis was performed without an inert gas atmosphere and with low catalyst loading. Investigations revealed that the presence of catalyst and PTC were essential for the catalysis reaction. The scope of aryl halide substrates was investigated by using the catalytic system under the optimized reaction conditions. It was also demonstrated that the catalytic system tolerated a variety of functionalized aryl halides in the reaction, including nitrile, nitro, acetyl, and ether groups. The new catalytic system was applied to a variety of imidazole derivatives to expand the scope of the methodology.

Copper-catalyzed N-arylation of diazoles with aryl bromides using KF/Al2O3: an improved protocol

Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Alikarami, Mohammad

, p. 5203 - 5205 (2006)

Copper-catalyzed N-arylation of diazoles can be accomplished using air-stable CuI as a copper source and 1,10-phenanthroline in the presence of KF/Al2O3 as a base. This is a simple and efficient method for the coupling of aryl bromide with diazoles. Different functionalized aryl bromides were coupled with diazoles using this system.

Nano-magnetic Fe3O4@TiO2/Cu2O composite: a simple, effective and reusable heterogeneous catalyst for ligand-free N-arylation of amines and nitrogen heterocycles

Nemati, Firouzeh,Elhampour, Ali

, p. 7611 - 7624 (2016)

Abstract: A practical and mild synthetic strategy has been investigated for the arylation of aromatic amines and nitrogen heterocycles using nano-magnetic-Fe3O4@TiO2/Cu2O composite and KOH as the base. The protocol does not require the use of expensive ligands. Notably, the catalyst is easily recoverable and reused by magnetic separation up to five runs without appreciable loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]

3-acetylcoumarin as a practical ligand for copper-catalyzed C-N coupling reactions at room temperature

Tao, Chuan-Zhou,Liu, Wei-Wei,Sun, Ji-You,Cao, Zhi-Ling,Li, Hui,Zhang, Ying-Fen

, p. 1280 - 1284 (2010)

The use of coumarin-based ligands was examined in copper-catalyzed C-N cross-coupling reactions. It was found that 3-acetylcoumarin constituted a new, practical ligand for the copper-catalyzed N-arylation of aliphatic amines and imidazole with aryl iodides at room temperature. Aryl bromides could also be aminated efficiently at 80 C. This readily available catalyst system, namely copper(I) iodide and 3-acetylcoumarin, provides a mild and practical method for the synthesis of aromatic amines. Georg Thieme Verlag Stuttgart New York.

A facile and efficient oxalyldihydrazide/ketone-promoted copper-catalyzed amination of aryl halides in water

Zhu, Xinhai,Su, Li,Huang, Liye,Chen, Gong,Wang, Jinlong,Song, Huacan,Wan, Yiqian

, p. 635 - 642 (2009)

A novel three-component catalyst CuO/oxalyldihydrazide/hexane-2,5-dione was a very convenient, economic, and effective catalytic system for the Ullmann-type C-N coupling reaction in water. Both aryl bromides and aryl iodides could be aminated by a variety of amines even at room temperature or with heating to afford very good isolated yields.

Copper complex-catalysed C-N coupling reaction of aryl iodides with nitrogen-containing heterocycles

Sajadi, S. Mohammad,Maham, Mehdi

, p. 128 - 129 (2014)

An efficient method for the copper-catalysed arylation of nitrogen-containing heterocycles is reported using 3-(diphenylphosphino) propanoic acid as a ligand in combination of CuCl. The C-N coupling reactions afford various N-arylated products in good to excellent yields.

Ligand-free copper(I) catalyzed N- and O-arylation of aryl halides

Sperotto, Elena,de Vries, Johannes G.,van Klink, Gerard P.M.,van Koten, Gerard

, p. 7366 - 7370 (2007)

A simple and industrially viable protocol for C-N and C-O coupling is reported here. Arylation of phenol, benzylamine and imidazole with aryl bromides is achieved using ligand-free Cu(I) halide salts in low catalytic amount (2.5 mol %).

Trinuclear copper(I) complexes with triscarbene ligands: Catalysis of C-N and C-C coupling reactions

Biffis, Andrea,Tubaro, Cristina,Scattolin, Elena,Basato, Marino,Papini, Grazia,Santini, Carlo,Alvarez, Eleuterio,Conejero, Salvador

, p. 7223 - 7229 (2009)

Novel synthetic routes for the preparation of trinuclear copper(I) complexes with triscarbene ligands are presented, which yield higher purity products than the one previously described. The first crystal structure of one of these complexes is reported an

Cu2O/nano-CuFe2O4: An efficient and magnetically recoverable catalyst for the ligand-free N-arylation of amines and nitrogen heterocycles with aryl halides

Elhampour, Ali,Nemati, Firouzeh,Kaveh, Mahdieh

, p. 223 - 225 (2016)

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.

Commercial drug norfloxacin as a novel ligand for the copper-catalyzed N-arylation of imidazole with aryl halides

Wu, Fengtian,Nan, Chenlong,Ma, Minyang,Li, Huiqin,Xie, Jianwei

, (2019)

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.

Direct N-arylation of azaheterocycles with aryl halides under ligand-free condition

Yang, Qichao,Wang, Yufang,Zhang, Baoji,Zhang, Mingjie

, p. 2389 - 2393,5 (2012)

A simple and efficient Ci£N cross-coupling method of aryl halides with various heterocycles was reported, by using 10 mol% of CuI as catalyst and 1.2 equiv. NaH as base. Aryl iodides, aryl bromides and many substituted aryl chlorides could efficiently react with heterocycles, providing variety of N-arylated products in good to excellent yields. The ligand-free catalyst system was stable in air and could be readily reused. An efficient, convenient and applicable method was developed for the N-arylation of azaheterocycles catalyzed by CuI and NaH under ligand free condition. Copyright

High-performance sono/nano-catalytic system: CTSN/Fe3O4-Cu nanocomposite, a promising heterogeneous catalyst for the synthesis of: N -arylimidazoles

Taheri-Ledari, Reza,Hashemi, Seyed Masoud,Maleki, Ali

, p. 40348 - 40356 (2019)

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

2-Aminopyrimidine-4,6-diol as an efficient ligand for solvent-free copper-catalyzed N-arylations of imidazoles with aryl and heteroaryl halides

Xie, Ye-Xiang,Pi, Shao-Feng,Wang, Jian,Yin, Du-Lin,Li, Jin-Heng

, p. 8324 - 8327 (2006)

Efficient and solvent-free copper-catalyzed N-arylations of imidazoles with aryl and heteroaryl halides have been demonstrated. In the presence of CuBr, 2-aminopyrimidine-4,6-diol, and TBAF (n-Bu4NF), a variety of imidazoles underwent the N-arylation reaction with aryl and heteroaryl halides smoothly in moderate to excellent yields. Noteworthy is that the reaction is conducted under solvent-free conditions.

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

Sardarian, Ali Reza,Zohourian-Mashmoul, Neda,Esmaeilpour, Mohsen

, p. 1101 - 1109 (2018)

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.].

Reduction system “vitamin C/glycerol” promoted copper(II)-catalyzed N-arylation

Cui, Chunna,Liu, Xiuping,Sun, Yijia,Wang, Peng,Wu, Fengtian,Wu, Ling,Yan, Fangming,Zeng, Rong,Zhang, Caihong

, (2022/02/17)

The common access to forming C-N bond is the copper-catalyzed Ullmann-type reaction. The relatively expensive and easily oxidized copper(I) is usually used in the reaction. Our group discovered that the “vitamin C/glycerol” reduction system could convert cheap and stable CuO to active low valence state copper species, as measured via X-ray photoelectron spectroscopy (XPS), to promote the C-N coupling reaction. In particular, 2-phenylindole, pyrrolo[1,2-a]quinoxaline, 1,2,4-triazole and 4-amino-7H-pyrrolo[2,3-d]pyrimidine derivative were obtained in the presence of CuO and reduction system “vitamin C/glycerol.” This method provided a simple and cost-effective approach to the preparation of N-arylation products.

L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols

Ding, Zhiqiang,Nie, Nan,Chen, Tian,Meng, Lingxin,Wang, Gongshu,Chen, Zhangpei,Hu, Jianshe

supporting information, (2020/12/21)

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.

Tunable aryl imidazolium ionic liquids (TAIILs) as environmentally benign catalysts for the esterification of fatty acids to biodiesel fuel

Ho, Wen-Yueh,Lin, Wesley,Lin, Yi-Jyun,Luo, Shun-Yuan,Pantawane, Amit,Su, Po-Fang,Thul, Mayur,Tseng, Shao-An,Wu, Hsin-Ru

, (2020/12/02)

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.

Copper pyrithione (CuPT)-catalyzed/mediated amination and thioarylation of (hetero)aryl halides: A competition

Cao, Ningtao,Song, Bao,Xie, Jianwei,Zhang, Jie

, (2021/11/08)

A facile method for the synthesis of N-arylheterocycles and di(hetero)aryl sulfides under mild condition is described. In these transformations, copper pyrithione (CuPT) was used as the copper catalyst for C─N coupling, while served as catalyst and coupled partner for C─S coupling with high yields and broad substrate tolerance. The S-arylation process was also utilized for the construction of valuable bioactive 2-sulfonylpyridine 1-oxide derivatives.

Process route upstream and downstream products

Process route

1H-imidazole
288-32-4

1H-imidazole

para-iodoanisole
696-62-8

para-iodoanisole

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

methoxybenzene
100-66-3

methoxybenzene

Conditions
Conditions Yield
With [Cu2(1,4-benzenedicarboxylate)2(1,4-diazabicyclo[2.2.2]octane)]n; potassium tert-butylate; In N,N-dimethyl-formamide; at 120 ℃; for 3h; Green chemistry;
1H-imidazole
288-32-4

1H-imidazole

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
With [Cu30I16(5-methyl-4-(p-tolyl)pyrimidine-2-thiolato)1210-S4)]; In methanol; for 5h; Temperature; Reagent/catalyst; Reflux;
99%
copper(I) oxide; In methanol; at 20 ℃; for 6h;
95%
With [CuI2(3,2'-pypzpym)]; oxygen; In water; acetonitrile; at 60 ℃; for 24h; under 760.051 Torr; Green chemistry;
95%
With potassium carbonate; In methanol; at 40 ℃; for 12h; Inert atmosphere;
94%
With triethylamine; In ethanol; at 20 ℃; for 12h;
94%
With Copper(II) immobilized into prolinamide-modified polyacrylonitrile fiber; In methanol; at 60 ℃; for 3h;
94%
With air; copper(l) chloride; In methanol; for 6h; Heating;
92%
With polystyrene-supported Cu(I) catalyst; In methanol; at 40 ℃; for 10h; Inert atmosphere;
92%
With solid phase supported pyridin-2-ylmethanimine-copper(II) complex; In methanol; at 40 ℃; for 14h;
92%
With dendrimer-encapsulated Cu(II) nanoparticles immobilized on superparamagnetic Fe3O4*SiO2 nanoparticles; In methanol; for 2h; Reflux;
92%
With potassium carbonate; In methanol; at 60 ℃; for 6h;
92%
With {copper(II)-[4-(2-pyridylazo)resorcinol]}-polystyrene supported catalyst; In methanol; at 40 ℃; for 14h; Inert atmosphere;
91%
With [Cu(II)(2-((2-hydroxybenzylidene)amino)phenolato)OAc] immobilizated onto poly(4-aminostyrene); In methanol; at 40 ℃; for 6h; Reagent/catalyst;
91%
With copper-exchanged fluorapatite; In methanol; at 20 ℃; for 5h;
90%
With copper-based metal-organic framework; air; In methanol; at 20 ℃; for 5h;
90%
With copper(I) sulfide; N,N,N,N,-tetramethylethylenediamine; In methanol; at 20 ℃; for 24h;
90%
With potassium carbonate; In methanol; at 60 ℃; for 3h; Green chemistry;
89%
With C21H16CuN2O2; potassium carbonate; In isopropyl alcohol; at 28 ℃; for 18h;
88%
With 2-(4-methoxybenzylidene)-N-phenylhydrazinecarbothioamide; copper(II) acetate monohydrate; potassium carbonate; In ethanol; at 20 ℃; for 20h;
82%
With copper diacetate; tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin; In water; at 50 ℃; for 4h; chemoselective reaction;
81%
With polystrene supported copper furfural catalyst; In methanol; at 40 ℃; for 18h; Inert atmosphere;
80%
With 4,4'-bis(perfluoro-1H,1H,2H,2H,3H,3H-nonyl)-2,2'-bipyridine; oxygen; copper diacetate; In water; at 20 ℃; for 24h; under 760.051 Torr;
78%
With silica-supported ionic liquid; In methanol; at 50 ℃; for 3h;
72%
With CuI-USY zeolite; In methanol; at 65 ℃; for 17h;
71%
With copper(I) 2-hydroxy-3-methylbenzoate; potassium carbonate; In methanol; at 65 ℃; for 3h;
69%
With C22H16CuN4O4(2+)*2CF3O3S(1-); potassium carbonate; In methanol; at 25 ℃; for 24h;
68%
With oxygen; di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; In dichloromethane; at 20 ℃;
63%
With pyridine; copper diacetate; air; 4 A molecular sieve; In dichloromethane; for 48h; Ambient temperature;
62%
With 2Na(1+)*CuC6H4(NCHC6H3OO3S)2(2-)=CuC6H4(NCHC6H3ONaO3S)2; In water; at 100 ℃; for 6h;
54%
With di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; tetrabutyl-ammonium chloride; oxygen; In water; at 20 ℃;
51%
With Cu2S:NiS2 core-shell nanoparticles encapsulated on porous carbon with reduced graphene oxide; air; In methanol; water; at 25 ℃; for 6h; Irradiation;
1H-imidazole
288-32-4

1H-imidazole

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
With copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 20 - 110 ℃;
95%
With potassium carbonate; In N,N-dimethyl-formamide; at 150 ℃; for 4h; Inert atmosphere; Green chemistry;
82%
With copper(l) iodide; caesium carbonate; dimethylbiguanide; In N,N-dimethyl-formamide; at 20 - 110 ℃; for 48.1667h;
65%
With oxalic acid hydrazide; phosphoric acid trihydrate; tetrabutylammomium bromide; 2,5-hexanedione; copper(II) oxide; In water; at 120 ℃; for 48h;
62%
With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 18h;
59%
With potassium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 36h;
52%
With 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid; copper(I) bromide; sodium hydroxide; In dimethyl sulfoxide; at 120 ℃; for 24h;
41%
With bis(8-hydroxyquinolato)copper(II); caesium carbonate; In dimethyl sulfoxide; at 100 ℃; for 48h;
32%
With copper(l) iodide; tetraethoxy orthosilicate; potassium carbonate; at 200 ℃; for 0.666667h; Microwave irradiation;
15%
With potassium carbonate; at 20 ℃; for 10h; Green chemistry;
73 %Chromat.
1H-imidazole
288-32-4

1H-imidazole

para-iodoanisole
696-62-8

para-iodoanisole

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
With potassium phosphate; copper(l) iodide; N-((4-nitro-1-oxy-pyridin-2-yl)methyl)oxalamic acid; In dimethyl sulfoxide; at 90 ℃; for 48h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;
99%
With C12H18ClCuN4O(1+)*ClO4(1-); caesium carbonate; In acetonitrile; at 80 ℃; for 24h; Reagent/catalyst; Inert atmosphere;
99%
With copper(l) iodide; 2-methyl-8-quinolinol; potassium carbonate; In dimethyl sulfoxide; at 90 ℃; for 24h; Inert atmosphere;
98%
With copper(I) oxide; potassium phosphate; N1,N2-bis(furan-2-ylmethyl)oxalamide; In acetonitrile; at 80 ℃; for 24h;
98%
With caesium carbonate; In dimethyl sulfoxide; at 110 ℃; for 24h; Green chemistry;
98%
With 2-(hydrazonomethyl)phenol; caesium carbonate; copper(I) oxide; In acetonitrile; at 50 ℃; for 24h;
97%
With 2-(2-tert-butylhydrazinecarbonyl)pyridine-1-oxide; tetrabutylammomium bromide; copper; potassium hydroxide; In water; at 120 ℃; for 12h; Reagent/catalyst; Temperature; Sealed tube; Green chemistry;
97%
With potassium carbonate; In water; at 100 ℃; for 24h; Reagent/catalyst; Temperature; High pressure;
97%
With copper(I) trifluoromethanesulfonate benzene; caesium carbonate; 1,10-Phenanthroline; (dibenzylidene)acetone; In xylene; at 110 ℃; for 24h;
96%
With 1,10-Phenanthroline; caesium carbonate; 1,5-diphenyl-1,4-pentadiene-3-one; copper(I) trifluoromethanesulfonate toluene adduct (1/1); In xylene; at 110 ℃;
96%
With 1,2,3-Benzotriazole; potassium tert-butylate; copper(l) iodide; In dimethyl sulfoxide; at 110 ℃; Further Variations:; Catalysts; Reagents; Solvents; Product distribution;
96%
With copper(l) iodide; caesium carbonate; dimethylbiguanide; In N,N-dimethyl-formamide; at 20 - 110 ℃; for 10.1667h;
96%
With triethylamine; In N,N-dimethyl-formamide; at 110 ℃; for 10h;
96%
With copper phthalocyanine; sodium hydroxide; In dimethyl sulfoxide; at 100 ℃;
96%
With copper(I) oxide; 1-(2-methylhydrazine-1-carbonyl)isoquinoline 2-oxide; tetrabutylammomium bromide; sodium hydroxide; In ethanol; water; at 120 ℃; for 12h; Temperature; Schlenk technique;
96%
With copper(I) oxide; 1-(2-methylhydrazine-1-carbonyl)isoquinoline 2-oxide; tetrabutylammomium bromide; sodium hydroxide; In ethanol; water; at 120 ℃; for 12h; Schlenk technique;
96%
With copper(l) iodide; 2-(2-benzoylhydrazine-1-carbonyl)-1-benzylpyrrolidine 1-oxide; caesium carbonate; In ethanol; at 80 ℃; for 12h; Inert atmosphere; Sealed tube;
96%
With potassium carbonate; bis(μ-iodo)bis[(-)-sparteine]dicopper(I); In dimethyl sulfoxide; at 115 ℃; for 7h;
95%
With potassium phosphate; copper(l) iodide; In N,N-dimethyl-formamide; at 35 - 40 ℃; for 40h; chemoselective reaction; Inert atmosphere;
95%
With copper(II) acetate monohydrate; caesium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 24h; Inert atmosphere;
95%
With copper(l) chloride; sodium hydroxide; 3-(diphenylphosphino)propionic acid; In dimethyl sulfoxide; at 120 ℃; for 14h; Solvent; Reagent/catalyst; Concentration; Catalytic behavior; Sealed tube; Inert atmosphere;
95%
With copper(l) iodide; (2-guanidinyl)ethyl-cyclen; In dimethyl sulfoxide; at 100 ℃; for 12h;
95%
1H-imidazole; With potassium carbonate; ethylene glycol; copper dichloride;
para-iodoanisole; for 0.5h; Reagent/catalyst; Microwave irradiation;
95%
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline; In xylene; at 130 - 140 ℃; for 15h;
94%
With Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate; In isopropyl alcohol; at 80 ℃; for 1.5h;
94%
With copper(l) iodide; tetrabutylammomium bromide; potassium hydroxide; at 110 ℃; for 6h;
93%
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; tetrabutylammomium bromide; sodium hydroxide; In water; at 120 ℃; for 48h; Inert atmosphere;
93%
With potassium carbonate; In N,N-dimethyl-formamide; at 152 ℃; for 12h;
93%
With 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid; copper(I) bromide; sodium hydroxide; In dimethyl sulfoxide; at 120 ℃; for 24h;
93%
With sodium hydroxide; In dimethyl sulfoxide; at 120 ℃; Inert atmosphere;
92%
With copper(l) iodide; 1H-tetrazol-1-ylacetic acid; sodium hydroxide; In dimethyl sulfoxide; at 110 ℃; for 12h; Reagent/catalyst; Solvent; Temperature; Sealed tube;
92%
With copper(I) oxide; caesium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 12h;
92%
With potassium hydroxide; In water; at 20 ℃; for 6h; Green chemistry;
92%
With copper(I) oxide; 2,6-bis(2-methylhydrazine-1-carbonyl)pyridine 1-oxide; tetrabutylammomium bromide; sodium hydroxide; In water; at 130 ℃; for 24h; Schlenk technique;
92%
With caesium carbonate; In N,N-dimethyl-formamide; at 140 ℃; for 24h; Temperature; Sealed tube;
92%
With copper(l) iodide; C14H28N2O10; caesium carbonate; In water; for 24h;
92%
With copper(l) iodide; N,N′-di-β-D-glucopyranosylethylenediamine; caesium carbonate; In water; at 100 ℃; for 24h; Reagent/catalyst; Temperature; Catalytic behavior; Green chemistry;
92%
With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 90 ℃; for 36h;
91%
With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 90 ℃; for 36h;
91%
With Cu(II)-exchanged fluorapatite; potassium carbonate; In dimethyl sulfoxide; at 110 ℃; for 14h;
91%
With copper(l) iodide; N-acetyl-D-glucosamine; caesium carbonate; In water; dimethyl sulfoxide; at 110 ℃; for 24h; Reagent/catalyst; Solvent; Temperature; Catalytic behavior;
91%
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride; at 110 - 115 ℃; for 48h;
90%
With copper(I) oxide; potassium hydroxide; indan-1,2,3-trione hydrate; In dimethyl sulfoxide; at 110 ℃; for 24h;
89%
With copper(l) iodide; tetraethoxy orthosilicate; potassium carbonate; at 200 ℃; for 0.666667h; Microwave irradiation;
89%
With potassium phosphate; copper; In dimethyl sulfoxide; at 80 ℃; for 5h; Inert atmosphere;
89%
With caesium carbonate; copper(II) oxide; L-histidine; at 150 ℃; for 2h; Reagent/catalyst; Sealed tube; Microwave irradiation;
89%
With copper(l) iodide; 1,10-phenanthroline N-oxide; caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 22h; Inert atmosphere;
88%
With 4.5Cu(2+)*4.5Ni(2+)*9C16H12N2*6C2O4(2-)*6H2O*P2W18O62(6-); sodium hydroxide; In dimethyl sulfoxide; at 120 ℃; for 12h;
87%
With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 80 ℃; for 24h; Inert atmosphere;
86%
With potassium carbonate; In dimethyl sulfoxide; at 100 ℃; for 18h; Inert atmosphere;
86%
With potassium hydroxide; In dimethyl sulfoxide; at 100 ℃; for 7.83333h;
86%
With (2-furyl)methyl alcohol; potassium phosphate; copper(l) iodide; In water; at 150 ℃; for 24h; Sealed tube; Green chemistry;
86%
With caesium carbonate; copper(I) bromide; In dimethyl sulfoxide; at 80 ℃; for 24h;
85%
With potassium carbonate; In water; dimethyl sulfoxide; at 110 ℃; for 24h; Reagent/catalyst; Temperature; Solvent; Catalytic behavior;
85%
With cetyltrimethylammonim bromide; potassium carbonate; at 20 ℃; for 0.166667h; Sonication;
85%
With copper(l) iodide; D-glucosamine hydrochloride; caesium carbonate; In water; dimethyl sulfoxide; at 100 ℃; for 10h; Reagent/catalyst; Solvent; Temperature;
84%
With potassium hydroxide; In dimethyl sulfoxide; at 100 ℃; for 8h;
84%
With bis(8-hydroxyquinolato)copper(II); caesium carbonate; In dimethyl sulfoxide; at 100 ℃; for 12h;
84%
With copper(l) iodide; C37H56N4O4; caesium carbonate; In 1,2-dimethoxyethane; at 80 ℃; for 20h; chemoselective reaction; Inert atmosphere; Sealed tube;
82%
With potassium carbonate; In dimethyl sulfoxide; at 120 ℃; for 18h; Inert atmosphere;
82%
With copper(l) iodide; 3-acetylcoumarin; caesium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 24h; Inert atmosphere;
81%
With potassium carbonate; In dimethyl sulfoxide; at 120 ℃; for 15h; Inert atmosphere;
81%
With copper (II)-fluoride; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 140 ℃; for 72h;
80%
With potassium carbonate; In dimethyl sulfoxide; at 120 ℃; for 12h; Inert atmosphere;
80%
With copper(l) iodide; N-tetradecyl lactosamine; caesium carbonate; In water; at 100 ℃; for 12h;
80%
With copper diacetate; caesium carbonate; In dimethyl sulfoxide; at 110 ℃;
80%
With copper(ll) sulfate pentahydrate; tetrabutylammomium bromide; caesium carbonate; butane-2,3-dione dioxime; In water; at 100 ℃; for 24h; under air;
79%
With dibenzylphosphoramidous acid 1,1'-binaphthyl-2,2'-diyl ester; caesium carbonate; copper(I) bromide; In N,N-dimethyl-formamide; at 90 ℃; for 24h;
78%
With potassium phosphate; copper(l) iodide; tetrabutylammomium bromide; In water; at 120 ℃; for 8h; Green chemistry;
78%
With potassium hydroxide; In water; at 120 ℃; for 18h; Inert atmosphere;
78%
With copper(l) iodide; potassium hydroxide; In dimethyl sulfoxide; at 80 ℃; for 20h; Inert atmosphere;
78%
With oxalic acid hydrazide; potassium phosphate tribasic trihydrate; tetrabutylammomium bromide; 2,5-hexanedione; copper(II) oxide; In water; at 25 - 140 ℃; for 0.1h; Microwave irradiation;
77%
With copper(l) iodide; tetrabutylammomium bromide; N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine; In water; at 125 ℃; for 12h;
77%
With 1,2,3-Benzotriazole; copper(l) iodide; In dimethyl sulfoxide; at 110 ℃; for 21h; Inert atmosphere;
77%
With MOF-199; sodium hydroxide; In dimethyl sulfoxide; at 120 ℃; for 12h; Sealed tube;
73%
With potassium hydroxide; In N,N-dimethyl-formamide; at 100 ℃; for 12h; Inert atmosphere; Green chemistry;
70%
With copper(I) oxide; potassium phosphate; tetrabutylammomium bromide; In water; at 130 ℃; for 24h; Closed system;
67%
With bis(1-dodecylimidazole)cupronium dichlorocuprate; tetrabutylammomium bromide; potassium carbonate; In water; at 80 ℃; for 12h; Green chemistry;
67%
With potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 12h; Inert atmosphere;
65%
With potassium hydroxide; In dimethyl sulfoxide; tert-butyl alcohol; at 110 ℃; for 11h;
64%
With Cu(2-thio-pyridine N-oxide)2; caesium carbonate; In dimethyl sulfoxide; at 100 ℃; for 12h;
58%
With copper(l) iodide; salicylaldehyde-oxime; caesium carbonate; In acetonitrile; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;
55%
With iron(III) oxide; potassium tert-butylate; In dimethyl sulfoxide; at 120 ℃; for 36h;
37%
With copper(l) iodide; 2,2'-biimidazole; caesium carbonate; In dimethyl sulfoxide; at 80 ℃; for 48h; Reagent/catalyst;
35%
With potassium carbonate; Cu(II)-NaY; In N,N-dimethyl-formamide; at 120 ℃; for 36h;
99 % Chromat.
With caesium carbonate; bis[hydrotris(3-Me-imidazolin-2-ylidene)borate]triCu(I) BF4; In dimethyl sulfoxide; at 100 ℃; for 24h;
50 % Spectr.
With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; Inert atmosphere;
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); caesium carbonate; In dimethyl sulfoxide; at 100 ℃; for 24h; Inert atmosphere;
67 %Spectr.
With copper(II) oxide; potassium hydroxide; In dimethyl sulfoxide; tert-butyl alcohol; at 110 ℃; for 24h; Inert atmosphere;
With C16H12ClN3OPdS; potassium hydroxide; In dimethyl sulfoxide; at 110 ℃; for 10h;
82 %Chromat.
4-methoxy-aniline
104-94-9

4-methoxy-aniline

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
Glyoxal; 4-methoxy-aniline; In methanol; water; at 20 ℃;
formaldehyd; With phosphoric acid; ammonium chloride; In methanol; water; Heating;
82%
Glyoxal; 4-methoxy-aniline; In methanol; water; at 20 ℃; for 16h;
formaldehyd; With phosphoric acid; ammonium chloride; In methanol; water; Heating;
75%
Glyoxal; 4-methoxy-aniline; In methanol; at 20 ℃; for 16h;
formaldehyd; With ammonium chloride; In methanol; at 65 ℃; for 1h;
With phosphoric acid; In methanol; for 48h; Reflux;
64%
Glyoxal; 4-methoxy-aniline; In methanol; at 20 ℃;
formaldehyd; With phosphoric acid; ammonium chloride;
With ammonium chloride;
With phosphoric acid; ammonium chloride; In methanol; at 60 ℃; for 24h;
1H-imidazole
288-32-4

1H-imidazole

p-methoxyphenyllead triacetate

p-methoxyphenyllead triacetate

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
With copper diacetate; In dichloromethane; at 20 ℃; for 3h;
85%
1H-imidazole
288-32-4

1H-imidazole

potassium 4-(methoxy)phenyltrifluoroborate

potassium 4-(methoxy)phenyltrifluoroborate

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
With copper(II) ethyl acetoacetate; In water; at 40 ℃; for 96h; under 760.051 Torr;
80%
1H-imidazole
288-32-4

1H-imidazole

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
With potassium carbonate; copper(I) bromide; In nitrobenzene; at 215 ℃;
1H-imidazole
288-32-4

1H-imidazole

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 18h;
90%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

2-methylimidazole
693-98-1

2-methylimidazole

1-(4-methoxyphenyl)-1H-imidazole
10040-95-6

1-(4-methoxyphenyl)-1H-imidazole

Conditions
Conditions Yield
With oxalic acid hydrazide; potassium phosphate tribasic trihydrate; tetrabutylammomium bromide; 2,5-hexanedione; copper(II) oxide; In water; at 25 - 140 ℃; for 0.1h; Microwave irradiation;
70%

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