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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.

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

Tunable aryl alkyl ionic liquids (TAAILs) based on the imidazolium cation were first reported in 2009. Since then, a series of TAAILs with different properties due to the electron-donating or -withdrawing effect of the substituents at the aryl ring has be

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.

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.

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.

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.

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.

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.

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.

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

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

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.

A set of new tunable aryl alkyl ionic liquids (TAAILs) based on the 1-aryl-3-alkyl imidazolium motif has been synthesized, in which the following variables were systematically changed: alkyl chain length, aryl substitution (group and position), and counte

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.

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.

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.

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

An experimentally simple, efficient, and inexpensive catalyst system was developed for the N-arylation of imidazole, indole, pyrrole, alkyl alcohol amines, and alkyl amines with aryl iodides and bromides. The reaction proceeds in water-ethanol media at 120 °C for 12 h with Cu2O as the catalyst, 1-(2-methylhydrazine-1-carbonyl)-isoquinoline 2-oxide (L2) as the ligand, NaOH as the base to generate a wide range of N-arylated products in moderate to excellent yields. Aqueous medium, ease of operation, and broad substrate scope give the process a benign environmental profile.

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.

A green and biodegradable carbohydrate-derived alkylamine was designed and employed as ligand for Ullmann type C-N coupling catalyzed by copper in water. The coupling of aryl iodide and N-nucleophiles were examined and moderate to excellent yields were obtained. In addition, the in-water coupling strategy was expanded successfully to the reaction of indoles with 4-iodoanisole. By measuring the solubility, it is speculated that carbohydrate-derived alkylamine plays the role of chelating copper and promoting the dissolution of 4-iodoanisole in water. Remarkably, this methodology was environmentally friendly and economical because of the use of aqueous media in place of organic solvents.

Eight bidentate NHC/Ru complexes, namely [Ru]-1-[Ru]-8, were designed and prepared. In particular, [Ru]-2 displayed extraordinary performance even in open air for the dehydrogenative coupling of alcohols and hydroxides. Notably, an unprecedentedly low catalyst loading of 250 ppm and the highest TON of 32 800 and TOF of 3200 until now were obtained.

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.

A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.

A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.

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.

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.

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

We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines. Furfuryl alcohol (FA) can be mixed with water to form the corresponding azeotrope (20 wt% of FA) and therefore can be easily recovered and reused. This protocol is efficiently applied to substrates with various electronic nature and affords the expected products (27 examples) in generally good to excellent yields. It has also been demonstrated that the protocol is both chemically and environmentally effective as the azeotropic mixture can be easily and almost quantitatively recovered at the end of the process.

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.].

Abstract: Cu2O/2,6-bis(2-methylhydrazine-1-carbonyl)pyridine 1-oxide was found to be an efficiently catalytic system for the N-arylation of imidazole, indole, benzimidazole, pyrrole, benzylamine and ethanolamine with aryl iodides and bromides by using NaOH as base in the presence of 20?mol% (n-Bu)4NBr, and water as solvent at 130?°C in 24?h, and giving the N-arylated products in moderate to excellent yields.

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

A ligand-free Cu-catalyzed protocol for the Ullmann-type N-arylation of N-containing heterocycles with aryl or heteroaryl iodides and bromides has been established. A broad range of functional groups is well tolerated on both of the cross-coupling partners, producing the desired products in good to excellent yields.

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.

An air-stable, highly active and versatile method for C─N bond forming reactions is reported. Under mild conditions using a highly reusable support-free Cu(II)–salen complex, structurally diverse N-aryl-substituted compounds were obtained via direct C─N bond forming reaction of HN-heterocycles with aryl iodides or three-component C─N bond forming reaction of 2-bromobenzaldehyde, aniline derivatives and sodium azide in good to excellent yields. C─N bond forming reaction for benzimidazole derivatives was also performed in the presence of the catalyst under ambient conditions. A series of hybrid benzimidazoles bearing morpholine, tetrazole and quinoxaline backbones were produced using this method. All reactions were performed in short times under air. The Cu(II) catalyst could be reused up to eight times in the direct cross-coupling reaction of 9H–carbazole with iodobenzene without any decrease in its catalytic activity.

The invention discloses a preparation method of an N-arylpyrazole compound and an N-arylimidazole compound. The method comprises the following steps: reacting at 20-120 DEG C for 6-48 hours by taking aryl halide and pyrazole or imidazole as substrates and copper salt as a catalyst in an organic solvent in the presence of alkali and a nitrogenous ligand under nitrogen protection; and after the reaction is finished, separating and purifying a reaction liquid to obtain the N-arylpyrazole compound or the N-arylimidazole compound. A product prepared by utilizing the method disclosed by the invention can not only be directly used, but also be used for other reactions as a substrate and has the advantages of moderation in adopted reaction condition, simple operation step and post-processing process, high yield and suitability for large-scale production.

Manipulating particle size is a powerful means of creating unprecedented applications in both inorganic and organic materials. Coordination polymers, which are emerging as a type of organic–inorganic hybrid materials, have attracted thriving interest in a variety of applications, but nanoscale coordination polymers have scarcely been touched. In this work, the pure-phase {Cu6[1,4-bis(imidazol-1-yl)butane]3I6}∞ coordination polymer with different sizes and morphologies was synthesized for the first time through a facile top-down route assisted by solvent etching. The size and morphology could be adjusted simply by varying the participating etching solvents. Our mechanistic investigations suggest that the bulk coordination polymer as a precursor in the etching solvents may experience a process of dispersion, dissolution, and recrystallization to generate the nanoscale counterpart. High catalytic activity of the nanoscale coordination polymer was observed in the N-arylation of imidazole aryl halides, and this was attributed to a high surface area and a low coordination number of unsaturated coordination sites. This simple and rapid preparation, requiring neither specialized equipment nor harsh conditions, suggests a wealth of potential for reducing the size of coordination polymers to comply with various practical applications.

N-Arylation of (benz)imidazoles and amines with diarylborinic acids as cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric hindrance appeared to affect the copper-catalyzed N-arylation using the high-order arylboron reagent more significantly than the electronic factors, especially for low reactive anilines and aliphatic amines.

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.

The invention discloses a methylene bridging 1,8-naphthyridine ligand and copper (I) complex, a preparing method and an application. The molecular formula of the methylene bridging 1,8-naphthyridine ligand and copper (I) complex is shown in the specificat

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.

1,4-Dihydroxyanthraquinone-copper(ii) supported on a superparamagnetic Fe3O4@SiO2 catalyst was employed for the N-arylation of nitrogen heterocycles and alkylamines with aryl halides to afford the corresponding coupled products in good to excellent yields without using external ligands or additives as promoters. Also, we have reported this recyclable catalytic system for efficient synthesis of 1-aryl-1,2,3-triazole derivatives in excellent yields. The desired triazoles were obtained from the reaction of the corresponding aryl boronic acid derivatives, alkyne, NaN3, and 0.5 mol% catalyst in water/acetonitrile as the solvent at room temperature without the additional use of an external reducing agent. These methods show notable advantages such as the heterogeneous nature of the catalyst, low catalyst loading, easy preparation, excellent yields, short reaction times and simplicity of operation. Also, the catalyst can be separated from the reaction mixture by applying a permanent magnet externally and can be reused in six consecutive reaction cycles without significant loss of activity.

Copper(I)-catalyzed N-arylation of imidazole with iodobenzene, its derivatives, and bromobenzene in poly(ethylene glycol) under microwave irradiation was studied. The influence of the following factors on the yield of arylation product was investigated: the nature of the source of copper and ligand, type of poly(ethylene glycol) (PEG) used, and substituents in iodoarene. An optimal catalytic system was selected: CuO/l-Hys/Cs2CO3/PEG-400, a possibility of recycling of copper-containing catalyst was demonstrated. N-Arylation of eight natural amino acids using catalysis with Cu2O/Cs2CO3/PEG-400 and microwave irradiation was studied, the dependence of the reaction results on temperature, duration of the process, and the ratio of the starting reagents was found. The highest yields of the target products were reached in the case of leucine, valine, and phenylalanine.

Ethylene glycol was used as an efficient and recoverable medium for the reaction of diazoles with aryl iodides and aryl bromides in the presence of CuCl2 as the catalyst and K2CO3 as the base. Consequently, imidazole, benzimidazole, and pyrazole reacted readily under microwave irradiation to give good to excellent yields of their corresponding N-arylated products in relatively short time periods. Apparently, ethylene glycol plays a dual role by activating the catalyst and also providing a homogenous medium for the processes. The reaction medium consisting of the solvent, the base, and the copper salt was recovered and reused successfully in the next several reactions.

Cu nanoparticles promoted N-arylation of NH-heterocycles with aryl halides is an effective and inexpensive method. In this synthetic protocol, good to excellent yields are obtained. Both aryl iodide and aryl bromide are compatible with the reaction conditions.

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.]

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.

The present invention provides a phosphorescent compound represented by chemical formula. In the chemical formula, R1 to R15 are respectively and individually selected from hydrogen, deuterium (D), halogen such as F, Cl, and Br, CF3, a cyano group, a C1 t

In present work, an efficient Cu(OAc)2·H2O catalyzed protocol in the absence of any additional ligand has been developed for the N-arylation of amines and nitrogen containing heterocycles using trivalent organobismuth reagents under mild conditions. This protocol tolerates a variety of functional groups on amines and the organobismuth reagent with a high degree of chemoselectivity.

Air- and moisture-stable and recyclable palladium nanoparticles supported on modified single-walled carbon nanotubes (SWCNT-Met/Pd) behave as very efficient heterogeneous catalysts in the Ullmann coupling of imidazoles and indoles with aryl iodides to afford the corresponding C-N coupling reactions under aerobic conditions. These cross coupled products were produced in excellent yields at low palladium loading (～0.2 mol%) and the heterogeneous catalyst can be readily recovered by simple filtration and reused five times without a noticeable loss in its catalytic activity.