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High performance white organic light-emitting diodes with blue fluorescence and red phosphorescence
Highly efficient blue emitting material (DAnP) consisting of anthracene and pyrene was designed and synthesized. The PLmax of the DAnP is 469 nm in the solution state and 480 nm in the film state. DAnP was used as non-doped emitting layer (EMLs) in OLEDs with the following structures: ITO/2-TNATA (60 nm)/NPB (15 nm)/DAnP (35 nm)/Alq3 (20 nm)/LiF (1 nm)/Al (200 nm). The DAnP device has current efficiency of 5.45 cd/A, power efficiency of 2.71 lm/W, and CIEs of (0.19, 0.40) at 10 mA/cm2. An efficient multilayer white organic light-emitting diode (WOLED) with the structure of ITO/NPB (30 nm)/CBP: 3 wt% Ir(piq)3 (10 nm)/DAnP (40 nm)/TPBi (40 nm)/LiF (1 nm)/Al (200 nm) was fabricated and characterized, where DAnP and tris(1-phenylisoquinoline) iridium (III) [Ir(piq)3] were used as a blue fluorescent emitter and a red phosphorescent emitter respectively. A WOLED showed current efficiency of 5.08 cd/A, power efficiency of 2.55 lm/W, and CIEs of (0.35, 0.36) at 10 mA/cm2.
Lee, Hayoon,Kang, Hyeonmi,Jung, Hyocheol,Kang, Seokwoo,Park, Jongwook
p. 5751 - 5754
(2017)
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Schiff bases-titanium (III) & (IV) complex compounds: Novel photocatalysts in Buchwald-Hartwig C–N cross-coupling reaction
Nine novel Schiff bases were derived from salicylic aldehyde and oxalic aldehyde, isolated, and their molecular and spatial structure were explored by a set of experiments (IR, CNMR, HNMR, CHN, SEM, XRD) and theoretical simulation (DFT def2-TZVP). A high potential was predicted in metal cations chelating. The isolated organic species were applied as the ligands in the reaction of complex formation with titanium (III) chloride and (IV) bromide and 12 novel complexes were synthesized and studied experimentally and theoretically. Using the UV–vis spectroscopic titration, the solution stability of the complexes was indicated. Depending on the nature of the Schiff base ligand, their formation constants were calculated in the range of 6.84–17.32. Using the DFT def2-TZVP theoretical method together with the experimental spectroscopic data, the coordination types of the ligands were investigated, and the structure of the complexes was proposed. The photocatalytic ability of the isolated complexes was tested in the C-N cross-coupling reaction under sunlight. Complexes exhibited high visible-light photocatalytic activity for a wide range of aromatic and benzylic amines including electron-withdrawing and electron-donating groups from moderate to good yields ranging in 50–85 %. The use of an inexpensive, clean, and renewable energy source (visible light) is the superiority of the developed photocatalytic systems.
Absalan, Yahya,Ghandi, Khashayar,Gholizadeh, Mostafa,Kovalchukova, Olga,Mahmoudi, Ghodrat,Sarvestani, Hossein Sabet,Shad, Nazanin Noroozi,Strashnov, Pavel
(2021/05/21)

Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions
Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Herein, we report the implementation of substoichiometric quantities of redox mediators to address limitations to Cu-catalyzed electrosynthesis. Mechanistic studies reveal that mediators serve multiple roles by (i) rapidly oxidizing low-valent Cu intermediates, (ii) stripping Cu metal from the cathode to regenerate the catalyst and reveal the active Pt surface for proton reduction, and (iii) providing anodic overcharge protection to prevent substrate oxidation. This strategy is applied to Chan-Lam coupling of aryl-, heteroaryl-, and alkylamines with arylboronic acids in the absence of chemical oxidants. Couplings under these electrochemical conditions occur with higher yields and shorter reaction times than conventional reactions in air and provide complementary substrate reactivity.
Walker, Benjamin R.,Manabe, Shuhei,Brusoe, Andrew T.,Sevov, Christo S.
supporting information
p. 6257 - 6265
(2021/05/07)

Chitosan nanoparticles functionalized poly-2-hydroxyaniline supported CuO nanoparticles: An efficient heterogeneous and recyclable nanocatalyst for N-arylation of amines with phenylboronic acid at ambient temperature
The present study aims to prepare an effective and eco-friendly nanocatalyst for the Chan–Lam coupling reaction of phenylboronic acid and amine in aerobic conditions. For this purpose, chitosan was extracted from shrimp shells waste by demineralization, deproteinization, and deacetylation processes and then converted to chitosan nanoparticles (CSN) by the ionic gelation with tripolyphosphate anions. Afterward, poly-2-hydroxyaniline (P2-HA) was grafted to chitosan nanoparticles (NPs) to employ as the support for CuO NPs. Characterization of the nanocatalyst was done using Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), mapping, energy-dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA). The CuO NPs were identified in the spherical shape with an average size of 17 nm. The prepared nanocatalyst exhibited excellent catalytic performance with a high turnover number (TON) and turnover frequency (TOF) for the Chan–Lam coupling reaction of phenyl boronic acid and amines with different electronic properties. The prepared catalyst could be readily recovered and reused for at least five runs without any noticeable change in structure and catalytic performance. Chitosan (CS) was prepared via demineralization, deproteinization, and deacetylation of shrimp shell and chitosan nanoparticles (CSN) were prepared via ionic gelation process. Polymerization of 2-HA on the CSN surface was done to increase functional groups and create active sites for CuO NPs attachments. CuO NPs-P2-HA-CSN nanocomposite has been shown high efficiently for the Chan–Lam coupling reaction.
Seyedi, Neda,Zahedifar, Mahboobeh
(2021/07/25)

Method for synthesizing diarylamine through N-arylation reaction of arylamine under copper catalysis
The invention provides a method for synthesizing diarylamine through an N-arylation reaction of arylamine under copper catalysis. The method comprises the following steps: S1, selecting a proper amount of a reaction reagent, a catalyst, a solvent and the like; S2, sequentially adding a reaction reagent, a catalyst, a solvent and the like into a reaction tube with a magnetic bar; S3, selecting a proper amount of AcOH, and adding the AcOH into the reaction tube; S4, heating the reaction tube; S5, performing oil bath treatment; S6, cooling to room temperature, and diluting; S7, extracting by using ethyl acetate; S8, washing the organic layer with saline water; S9, drying on anhydrous Na2SO4; S10, evaporating under vacuum; and S11, purifying the residues into the pure product through silica gel chromatography. A scheme that arylamine and an environmentally-friendly and stable aryl silicon reagent are subjected to an N-arylation reaction under the catalysis of a cheap copper reagent is provided, Cu(OAc)2 is used as a catalyst to react in DMSO in the atmosphere of O2, the conversion reactivity is good, the substrate range is wide, and the method has good tolerance to reaction substrates with various functional groups under mild reaction conditions.
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Paragraph 0062-0063; 0072; 0073; 0080; 0081

(2021/07/14)

Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids
The synthesis of diarylamine is extremely important in organic chemistry. Herein, a novel electrochemical reductive arylation of nitroarenes with arylboronic acids was developed. A variety of diarylamines were synthesized without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell and several derivatization reactions were carried out smoothly. Cyclic voltammetry experiments and mechanism studies showed that acetonitrile, formic acid, and triethyl phosphite all played a role in promoting this reductive arylation transformation.
Wang, Dan,Wan, Zhaohua,Zhang, Heng,Alhumade, Hesham,Yi, Hong,Lei, Aiwen
p. 5399 - 5404
(2021/10/20)

A Novel Modified Cross-Coupling of Phenols and Amines Using Dichloroimidazolidinedione (DCID)
Phenols are considered as an ideal alternative to aryl halides as coupling partners in cross-coupling reactions. In the present work a copper-catalyzed cross-coupling of phenols with various aromatic and aliphatic amines for the synthesis of secondary aryl amines using dichloroimidazolidinedione (DCID) as a new and efficient activating agent has been developed. Substituted phenols were compatible with the standard reaction conditions. The two proposed mechanisms, which are based on the oxidation addition of copper with Ar-OMCID (MCID: Monochloroimidazolidinedione), are also discussed.
Madankar, Kamelia,Mokhtari, Javad,Mirjafary, Zohreh
supporting information
p. 1725 - 1729
(2020/09/01)

Diaza crown-type macromocycle (kryptofix 22) functionalised carbon nanotube for efficient Ni2+ loading; A unique catalyst for cross-coupling reactions
Raising the capability of supporting and suppressing the leaching possibility to a very insignificant level has still remained challenging for some class of transition metals, i.e. Ni2+. Here we present the covalent functionalisation of macrocyclic ligand, 4,13-diaza-18-crown-6 (kryptofix 22), on the surface of carbon nanotube (CNT), leading to a unique adsorptive capability for supporting Ni2+. This material was incorporated as a promising catalyst in coupling reactions including C[sbnd]C, CN, and CO[sbnd][sbnd] cross-coupling reactions. We demonstrate that the kryptofix 22 functionalisation on the surface of CNT has a key role in the enhancement of the adsorption capability Ni2+ and subsequent catalytic activity. We further prove that this ligand causes a significant boost in the recyclability of the reactions due to the extremely trivial Ni2+ leaching from the CNT's surface during the reactions.
Aalinejad, Michael,Doustkhah, Esmail,Pesyan, Nader Noroozi
(2020/07/13)

Cu-ACP-Am-Fe3O4@SiO2: an efficient and recyclable heterogeneous catalyst for the Chan–Lam coupling reaction of boronic acids and amines
Abstract: We have developed an efficient method for Cu-ACP-Am-Fe3O4@SiO2 catalyzed Chan–Lam coupling of phenylboronic acid with primary amine furnished secondary amines. The catalyst offered virtues like mild reaction conditions, magnetically separable, and reusable and exhibits excellent performance in terms of good product yield and high turnover number. Graphic abstract: [Figure not available: see fulltext.]
Vibhute, Sandip P.,Mhaldar, Pradeep M.,Gaikwad, Dipak S.,Shejwal, Rajendra V.,Pore, Dattaprasad M.
p. 87 - 92
(2020/01/03)

Aromatic amine compound and applications thereof
The invention discloses an aromatic amine compound and applications thereof, and belongs to the technical field of semiconductors, wherein the structure of the aromatic amine compound provided by theinvention is represented by a general formula (1). The invention also discloses applications of the compound. According to the invention, the compound provided by the invention is an aromatic amine compound, has strong hole transport capability and high hole mobility, can be used as a hole transport material, and can improve the efficiency of an organic electroluminescent device at a high hole transport rate; and under a proper LUMO energy level, the compound can achieve an electron blocking effect, improve the recombination efficiency of excitons in a light-emitting layer, reduce the efficiency roll-off under a high current density, reduce the device voltage and improve the current efficiency and the service life of a device.
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Paragraph 0126; 0135-0136

(2020/04/02)

Design, preparation and characterization of aerogel NiO-CuO-CoO/SiO2 nanocomposite as a reusable catalyst for C-N cross-coupling reaction
Aerogels are porous, non-crystalline solid materials with high specific surface space, plentiful three-dimensional (3D) porous construction, ultra-low density and significant porosity. The aerogel nanocomposite is produced using sol-gel and supercritical drying processes. CO2 supercritical drying (SCD) is the most powerful process, ensuring optimal product properties such as high porosity, low density, and high thermal conductivity. On this account, we used the CO2 supercritical drying method to produce NiO-CuO-CoO/SiO2 nanocomposite aerogels and applied it as a reusable catalyst for the C-N cross-coupling reaction (Buchwald-Hartwig amination). Powerful catalytic activity for the C-N cross-coupling reaction was obtained for the new nanocomposite aerogel, that is, NiO-CuO-CoO/SiO2. The catalyst was characterized by X-ray Powder Diffraction (XRD), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDS), elemental mapping and Brunauer-Emmett-Teller (BET). Also, organic compounds were identified by melting point, Fourier-transform infrared spectroscopy (FT-IR) and hydrogen-1 nuclear magnetic resonance (1H NMR) analyses.
Ghasemi, Amir Hossein,Naeimi, Hossein
supporting information
p. 5056 - 5063
(2020/04/09)

Imidazole-directed fabrication of three polyoxovanadate-based copper frameworks as efficient catalysts for constructing C-N bonds
A synthetic pathway for the directed preparation of three novel polyoxovanadate-based copper frameworks (POVCFs), i.e., [Cu0.5(1-ipIM)2]2[V4O11] (POVCF 1), [Cu(1-ipIM)2](VO3)2 (POVCF 2) and [Cu(1-pIM)4](HpIM)4[V10O28] (POVCF 3) (1-ipIM = 1-isopropylimidazole; 1-pIM = 1-propylimidazole) using bifunctional imidazole molecules as organic ligands and base has been developed. Systematic studies revealed that the variable base enviroment in the reaction is the key step in the preparation of 1D to 3D supermolecular networks of POVCFs 1-3. Single crystal X-ray diffraction analyses demonstrated that the Cu2+ atoms of POVCFs 1-2 were coordinated with four imidazole derivative molecules and two different polyoxovanadate {[V4O11]2- and [V10O28]6-} clusters, respectively, exhibiting a [CuN4O2] binding set and a distorted octahedral geometry. Specifically, POVCF 1 exhibited adjacent [V4O11]2- that dangle up and down arranged in a parallel 2D network and further coordinated with [Cu(1-ipIM)4]2+ to form a 3D supramolecular structure. However, POVCF 3 presented one tetrahedral coordinated vanadium atom and one four-coordinated copper atom and they further gave rise to a 1D network by the Cu-O and V-O bonds. More importantly, these POVCFs were further studied in the construction of C-N bond reactions of primary amines under mild conditions, and it was found that POVCF 1 displayed efficient heterogeneous catalytic activities in the Chan-Lam reaction (yields up to 89%). This journal is
Gong, Shuwen,Gu, Yuxiao,Huang, Xianqiang,Li, Jikun,Li, Qiang,Qi, Yuquan,Shen, Guodong
p. 10970 - 10976
(2020/09/02)

Chan-Evans-Lam C?N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle
In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan-Evans-Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4-t-butyl-2,5-bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter-anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C?N-bond formation. Forty-three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C?N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C?N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C?N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).
Akatyev, Nikolay,Il'in, Mikhail,Il'in, Mikhail,Peregudova, Svetlana,Peregudov, Alexander,Buyanovskaya, Anastasiya,Kudryavtsev, Kirill,Dubovik, Alexander,Grinberg, Valerij,Orlov, Victor,Pavlov, Alexander,Novikov, Valentin,Volkov, Ilya,Belokon, Yuri
p. 3010 - 3021
(2020/04/29)

Modified graphene supported Ag-Cu NPs with enhanced bimetallic synergistic effect in oxidation and Chan-Lam coupling reactions
Herein, well dispersed Ag-Cu NPs supported on modified graphene have been synthesized via a facile and rapid approach using sodium borohydride as a reducing agent under ambient conditions. Dicyandiamide is selected as an effective nitrogen source with TiO2 as an inorganic material to form two kinds of supports, labelled as TiO2-NGO and NTiO2-GO. Initially, the surface area analysis of these two support materials was carried out which indicated that N-doping of GO followed by anchoring with TiO2 has produced support material of larger surface area. Using both types of supports, ten nano-metal catalysts based on Ag and Cu were synthesized. Benefiting from the bimetallic synergistic effect and larger specific surface area of TiO2-NGO, Cu?Ag-TiO2-NGO is found to be a highly active and reusable catalyst out of other synthesized catalysts. It exhibits excellent catalytic activity for oxidation of alcohols and hydrocarbons as well as Chan-Lam coupling reactions. The nanocatalyst is intensively characterized by BET, SEM, HR-TEM, ICP-AES, EDX, CHN, FT-IR, TGA, XRD and XPS. This journal is
Choudhary, Anu,Gupta, Monika,Kaur, Manpreet,Paul, Satya,Sharma, Chandan,Sharma, Nitika
p. 30048 - 30061
(2020/10/06)

Recyclable bimetallic CuMoO4 nanoparticles for C-N cross-coupling reaction under mild conditions
Herein we disclosed inexpensive copper(ii) bimetallic CuMoO4 nanoparticles for the C-N cross-coupling reaction of alkyl and aryl amines with haloarenes. The reaction proceeds under mild and ligand free conditions. The catalyst is recyclable and effective for a wide range of amines and haloarenes. Here, the efficiency of the Cu(ii) catalyst is increased by doping molybdenum metal. The bimetallic nanoparticles are anticipated to proceed via normal oxidative addition and reductive eliminations.
Panigrahi, Reba,Panda, Subhalaxmi,Behera, Pradyota Kumar,Sahu, Santosh Kumar,Rout, Laxmidhar
supporting information
p. 19274 - 19278
(2019/12/24)

Diamines as interparticle linkers for silica-titania supported PdCu bimetallic nanoparticles in Chan-Lam and Suzuki cross-coupling reactions
A series of highly efficient amine functionalized SiO2-TiO2 supported bimetallic PdCu catalysts with varied metal composition have been synthesized. Ethane-1,2-diamine, butane-1,4-diamine and hexane-1,6-diamine were employed as interparticle linkers for amine functionalization of a SiO2-TiO2 support material so as to study the effect of pendant chain length on stabilization and immobilization of bimetallic nanoparticles. The shortest carbon chain length on the support provided the best results, which may be due to the trapping of metal nanoparticles more efficiently by the basic nitrogen sites. The catalytic activities of these materials were evaluated for C-N and C-C coupling reactions. The most active catalyst, Pd1Cu1@12DA-STS, was characterized by various techniques including SEM, HR-TEM, ICP-AES, XRD, FTIR, EDX, CHN analysis and TGA studies. Moreover, the synthesized catalyst was found to be recyclable for up to five runs without significant loss of activity.
Jamwal, Babita,Kaur, Manpreet,Sharma, Harsha,Khajuria, Chhavi,Paul, Satya,Clark
p. 4919 - 4928
(2019/03/26)

Peptide Nanofiber Templated Zinc Oxide Nanostructures as Non-precious Metal Catalyzed N-Arylation of Amines, One-Pot Synthesis of ImidazoHeterocycles and Fused Quinazolines
In the present study, peptide nanofiber was used to immobilize zinc oxide. This nanoparticle was prepared through self-assembly in an aqueous solution. The structural properties of the prepared catalyst were examined by a series of techniques, such as FT-IR, EDS, SEM, TEM, XRD, ICP-OES (inductively coupled plasma optical emission spectrometry), and ultraviolet–visible (UV–Vis) spectroscopy. TEM images showed the necklace model for peptide nanofiber decorated with zinc oxide. The versatility of the method was investigated by N-arylation using reaction of amines with hydroxybenzotriazole as a novel phenylating reagent, one-pot synthesis of imidazoheterocycles by a three-component reaction of 2-aminopyridine, aldehyde, terminal alkyne and preparation of tetracyclic quinazolinone ring by one-pot reaction of isatoic anhydride, amine, and ninhydrin. High yields, low cost of catalyst, environmental friendliness, efficient recovery and recyclability of catalyst are the most important features of this catalytic system.
Taherinia, Zahra,Ghorbani-Choghamarani, Arash,Hajjami, Maryam
p. 151 - 168
(2018/10/26)

Electrochemically Enabled Chan-Lam Couplings of Aryl Boronic Acids and Anilines
The Chan-Lam reaction remains a highly utilized transformation for C-N bond formation. However, anilines remain problematic substrates due to their lower nucleophilicity. To address this problem, we developed an electrochemically mediated Chan-Lam coupling of aryl boronic acids and amines utilizing a dual copper anode/cathode system. The mild conditions identified have enabled the preparation of a wide range of functionalized biarylanilines in good yields and chemoselectivities.
Wexler, Ryan P.,Nuhant, Philippe,Senter, Timothy J.,Gale-Day, Zachary J.
supporting information
p. 4540 - 4543
(2019/06/27)

CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
Mohammadinezhad, Arezou,Akhlaghinia, Batool
supporting information
p. 15525 - 15538
(2019/10/19)

Nickel-catalyzed N-arylation of amines with arylboronic acids under open air
In this study, a well-defined, novel NHC-Ni complex was developed and used to catalyze the N-arylation of alkyl- and arylamines with arylboronic acids in a rare version of Chan-Lam coupling. Although the same coupling using copper catalysts has been widely studied, the nickel-catalyzed version is rare and normally requires 10–20 mol% catalyst loading. This novel NHC-Ni complex in combination with 4,4′-dimethyl-2,2′-bipyridine, however, proved to be an effective catalyst that lowered the required catalyst loading to only 2.0 mol%.
Ando, Shin,Hirota, Yurina,Matsunaga, Hirofumi,Ishizuka, Tadao
supporting information
p. 1277 - 1280
(2019/04/10)

Copper-Catalyzed NaBAr 4-Based N-Arylation of Amines
Using NaBAr 4 as an arylating agent, the formation of carbon-heteroatom bonds by a Cham-Lam cross-coupling reaction in the presence of catalytic copper(II) acetate monohydrate in acetonitrile at room temperature under air is described. The investigation of reaction scope suggests that several aliphatic and aromatic amines are compatible. In particular, the reaction of alkylamine and NaBAr 4 proceeds smoothly to offer the corresponding products in good to excellent yields.
Yang, Qin,Lei, Xiaoli,Yin, Zhijian,Deng, Zhihong,Peng, Yiyuan
supporting information
p. 538 - 544
(2019/01/10)

Reductive Molybdenum-Catalyzed Direct Amination of Boronic Acids with Nitro Compounds
The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C?N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. Moreover, this general and step-economical synthesis of aromatic secondary amines showcases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.
Suárez-Pantiga, Samuel,Hernández-Ruiz, Raquel,Virumbrales, Cintia,Pedrosa, María R.,Sanz, Roberto
supporting information
p. 2129 - 2133
(2019/01/25)

Transition-Metal-Free N-Arylation of Amines by Triarylsulfonium Triflates
A simple and efficient method for transition-metal-free N-arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 °C in the presence of tBuOK or KOH to give the corresponding mono N-arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N-phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N-phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N-arylated products when using 4-substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr?N bonds.
Tian, Ze-Yu,Ming, Xiao-Xia,Teng, Han-Bing,Hu, Yu-Tian,Zhang, Cheng-Pan
p. 13744 - 13748
(2018/09/14)

Metal-free synthesis of secondary amines by the reaction of tosyl triazene and aryl boronic acid
A metal free noncatalytic amination process has been developed for the synthesis of N-substituted aniline using a new amine source. The amine source p-toluene sulfonyl triazene (PhN?NNHTs) has been prepared by treating aryldiazonium salt with p-tosylamide. Various unsymmetrical amines could be synthesized by treating this reagent and boronic acid in toluene at 110 °C in the presence of DBU and 4 ? molecular sieve. A large variety of N-substituted aniline could be synthesized with moderate yield.
Sarma, Manas Jyoti,Phukan, Prodeep
p. 656 - 662
(2018/02/19)

Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.
Roscales, Silvia,Csák?, Aurelio G.
p. 1667 - 1671
(2018/03/23)

Synthesis and characterization of MCM-41-Biurea-Pd as a heterogeneous nanocatalyst and using its catalytic efficacy in C–C, C–N and C–O coupling reactions
MCM-41-Biurea-Pd is introduced as a new, heterogeneous and reusable catalyst for C–C and C–heteroatom bond formation between various aryl halides, phenols and amines, in the presence of Ph3SnCl (Stille reaction) in PEG-400 as a green solvent at room temperature. The structure of the functionalized MCM-41 was analysed using various techniques.
Batmani, Hana,Noroozi Pesyan, Nader,Havasi, Forugh
(2018/07/31)

Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines
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.
Han, Yi,Zhang, Mo,Zhang, Ya-Qing,Zhang, Zhan-Hui
p. 4891 - 4900
(2018/11/21)

Cu-doped CoFe2O4 nanoparticles as magnetically recoverable catalyst for C–N cross-coupling reaction
A new hybrid catalyst has been developed by immobilizing copper acetate onto surface of cobalt ferrite magnetic nanoparticles bearing N–O chelating ligand. The magnetic core of the catalyst was synthesized via ultrasound assisted co-precipitation method and characterized by FT-IR, XRD, EDX, SEM, TEM, TGA and VSM analysis. The catalyst was found to be very active for C–N bond forming reaction. Coupling of amines and aryl boronic acid could be achieved in high yield in methanol in presence of triethylamine at room temperature. After completion of the reaction the catalyst could be recovered using an external magnet and reused for consecutive catalytic cycles without significant decrease in the catalytic activity.
Dutta, Mintu Maan,Phukan, Prodeep
p. 38 - 42
(2018/03/01)

Organic metal compounds and organic light emitting diodes comprising the same
PURPOSE: An organic metal compound and an organic electroluminescent device containing the same are provided to ensure excellent thermal property and luminescence efficiency, and to be used in a display and a light. CONSTITUTION: An organic metal compound contains a compound of chemical formula 1. An organic electroluminescent device contains the organic metal compound of chemical formula 1. The compound is contained in a light emitting layer between anode and cathode. The organic electroluminescent device comprises one or more layers selected from a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer between the anode and the cathode.
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Paragraph 0437; 0444; 0446-0449

(2018/10/19)

Polymerization-Enhanced Photosensitization
Effective photosensitizers are highly desirable in many applications, such as photodynamic therapy, photocatalytic organic waste decomposition, and synthetic chemistry. Herein, we demonstrate polymerization-enhanced photosensitization, in which conjugated-polymer-based photosensitizers show much higher efficiency in singlet oxygen (1O2) production than their small-molecule analogs. Based on small-molecule photosensitizers SM1–SM4 with long wavelength emission, four conjugated polymer photosensitizers, CP1–CP4, were prepared. Interestingly, the conjugated polymer photosensitizers CP1–CP4 showed 5.06-, 5.07-, 1.73-, and 3.42-fold higher 1O2 generation efficiency than SM1–SM4, respectively. The improved intersystem crossing process from the singlet excitation states to the triplet excitation states and improved light-harvesting ability are essential to the enhancement of 1O2 generation efficiency. To illustrate the advantages of conjugated polymer photosensitizers on various applications, we demonstrate the superior performance of CP1 by using photoinduced organic waste decomposition, photoinduced organic oxidation reaction, and photodynamic cancer therapy as examples. Organic photosensitizers (PSs) are unique compounds that can absorb light or electromagnetic waves and transform them into reactive molecules, such as singlet oxygen (1O2). Highly efficient PSs are in great demand for many applications, such as photodynamic therapy, photoinduced organic waste decomposition, and photocatalytic organic synthesis. In this work, we propose the concept of polymerization-enhanced photosensitization. We show that polymerization of small-molecule PSs into conjugated polymers could significantly enhance their efficiency in 1O2 production with superior performance to that of commercial PSs (e.g., Ce6) in various applications. This concept is anticipated to open up new opportunities for rational photosensitizer design and applications. Effective photosensitizers are highly desirable in many applications. Herein, Liu and co-workers demonstrate polymerization-enhanced photosensitization, in which conjugated-polymer-based photosensitizers show much higher efficiency in singlet oxygen (1O2) production than their small-molecule analogs. Based on this concept, conjugated polymer photosensitizer CP1 with an aggregation-induced emission feature is proposed to show highly efficient 1O2 generation ability superior to that of its small-molecule analog SM1 and commercial photosensitizer Ce6 in photodynamic therapy, organic waste decomposition, and photocatalytic reactions.
Wu, Wenbo,Mao, Duo,Xu, Shidang,Kenry,Hu, Fang,Li, Xueqi,Kong, Deling,Liu, Bin
supporting information
p. 1937 - 1951
(2018/06/29)

Chan-Evans-Lam Couplings with Copper Iminoarylsulfonate Complexes: Scope and Mechanism
Copper(II) pyridyliminoarylsulfonate complexes with chloride or triflate counteranions were employed in Chan-Evans-Lam (CEL) couplings of N-nucleophiles and arylboronic acids. The complexes avoided typical side reactions in CEL couplings, and an excess of boronic acid was not required. Water was tolerated, and addition of neither base nor other additives was necessary. Primary amines, acyclic and cyclic secondary amines, anilines, aminophenol, imidazole, pyrazole, and phenyltetrazole can be quantitatively arylated at either 25 or 50 °C with 2.5 mol % of the catalyst. Reaction kinetics were investigated in detail. Kinetic and spectroscopic studies provide evidence for the formation of unproductive copper-substrate complexes. Formation of an aniline-phenylboronic acid adduct was responsible for the zero-order dependence of reaction rates on phenylboronic acid concentration. Kinetic evidence indicates that the order of reaction steps is transmetalation, nucleophile coordination, and oxidation. Couplings performed poorly with electron-deficient arylboronic acids, due to a slower Cu(II)/Cu(III) oxidation in the catalytic cycle. Photoredox catalysis partially resolved this problem, but addition of copper acetate as an external oxidant proved to be more efficient.
Hardouin Duparc, Valérie,Bano, Guillaume L.,Schaper, Frank
p. 7308 - 7325
(2018/07/05)

Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV=O Catalysis
A main group-catalyzed method for the synthesis of aryl- and heteroarylamines by intermolecular C-N coupling is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane) and a terminal hydrosilane reductant (phenylsilane) to drive reductive intermolecular coupling of nitro(hetero)arenes with boronic acids. Applications to the construction of both Csp2-N (from arylboronic acids) and Csp3-N bonds (from alkylboronic acids) are demonstrated; the reaction is stereospecific with respect to Csp3-N bond formation. The method constitutes a new route from readily available building blocks to valuable nitrogen-containing products with complementarity in both scope and chemoselectivity to existing catalytic C-N coupling methods.
Nykaza, Trevor V.,Cooper, Julian C.,Li, Gen,Mahieu, Nolwenn,Ramirez, Antonio,Luzung, Michael R.,Radosevich, Alexander T.
supporting information
p. 15200 - 15205
(2018/11/30)

Meta - And para -Functionalized Thermally Crosslinkable OLED-Materials through Selective Transition-Metal-Catalyzed Cross-Coupling Reactions
Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9 H -fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9 H -fluorenes that underwent end-functionalization by the Suzuki-Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9 H -fluorenes. Novel meta -functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta -substituted materials than their para -functionalized analogues.
Hempe, Matthias,Schnellb?cher, Lutz,Wiesner, Tobias,Reggelin, Michael
p. 4489 - 4499
(2017/09/26)

High Catalytic Activity of Peptide Nanofibres Decorated with Ni and Cu Nanoparticles for the Synthesis of 5-Substituted 1H-Tetrazoles and N-Arylation of Amines
A rapid development of a new methodology for decarboxylative N-arylation of carboxylic acids and the preparation of 5-substituted 1H-tetrazoles catalysed by peptide nanofibres decorated with Cu and Ni nanoparticles is presented. Compared with conventional aryl halides, benzoic acids are extremely interesting and environmentally friendly options for the synthesis of secondary aryl amines.
Ghorbani-Choghamarani, Arash,Taherinia, Zahra
p. 1127 - 1137
(2017/10/10)

Copper immobilized on magnetite nanoparticles coated with ascorbic acid: An efficient and reusable catalyst for C─N and C─O cross-coupling reactions
In a continuation of using magnetic nanoparticle (MNP)-supported catalysts, ascorbic acid (readily available, very safe and with strong affinity to MNPs) was used instead of the commonly used silica layer coating. This hybrid was used for immobilizing copper nanoparticles to produce Cu/ascorbic acid@MNPs catalyst. The catalyst was characterized and used in carbon–oxygen and carbon–nitrogen (various substrates) cross-coupling reactions in aqueous media and at room temperature with excellent product yields. Furthermore, the catalyst could be quickly and completely recovered using an external magnetic field and reused for six reaction cycles without significant change in catalytic activity.
Hajipour, Abdol R.,Check, Maryam,Khorsandi, Zahra
(2017/09/30)

Copper Oxide Nanoparticles as a Mild and Efficient Catalyst for N-Arylation of Imidazole and Aniline with Boronic Acids at Room Temperature
The present work describes the excellent catalytic activity of copper(II) oxide nanoparticles (NPs) towards N-arylation of aniline and imidazole at room temperature. The copper(II)oxide NPs were synthesized by a thermal refluxing technique and characterized by FT-IR spectroscopy; powder XRD, SEM, EDX, TEM, TGA, XPS, BET surface area analysis, and particle size analysis. The size of the NPs was found to be around 12 nm having a surface area of 164.180 m 2 g -1.The catalytic system was also found to be recyclable and could be reused in subsequent catalytic runs without a significant loss of activity.
Borah, Raju Kumar,Raul, Prasanta Kumar,Mahanta, Abhijit,Shchukarev, Andrey,Mikkola, Jyri-Pekka,Thakur, Ashim Jyoti
p. 1177 - 1182
(2017/06/13)

Sulfonato-imino copper(II) complexes: Fast and general Chan-Evans-Lam coupling of amines and anilines
Sulfonato-imine copper complexes with either chloride or triflate counteranions were prepared in a one-step reaction followed by anion-exchange. They are highly active in Chan-Evans-Lam couplings under mild conditions with a variety of amines or anilines, in particular with sterically hindered substrates. No optimization of reaction conditions other than time and/or temperature is required.
Hardouin Duparc,Schaper
supporting information
p. 12766 - 12770
(2017/10/11)

Sulfonato-diketimine Copper(II) Complexes: Synthesis and Application as Catalysts in Chan-Evans-Lam Couplings
Copper complexes bearing a diketimino-sulfonate ligand, LCu(NO3)(NCMe), were prepared and proved to be stable to water for several hours in solution. Prolonged standing in the presence of water or strong bases led to desulfonation of the ligand. LCu(NO3) was inactive in the polymerization of lactide (in the presence of benzyl alcohol), but showed high activity for the Chan-Evans-Lam coupling of a variety of amines and anilines. Couplings do not require addition of base, ligand, or molecular sieves. Mechanistic investigations indicate a catalytic cycle involving dioxygen as the required oxidant, precoordination of boronic acid to the sulfonate group, and transmetalation occurring prior to reaction with the nucleophile.
Hardouin Duparc, Valérie,Schaper, Frank
p. 3053 - 3060
(2017/09/05)

Cu2(BDC)2(BPY)-MOF: An efficient and reusable heterogeneous catalyst for the aerobic Chan-Lam coupling prepared via ball-milling strategy
Nanoporous Cu2(BDC)2(BPY)-MOF was used as efficient and reusable heterogeneous catalyst to effect the aerobic cross-coupling of aromatic amines and phenyl boronic acid (Chan-Lam coupling). Ball-milling strategy was utilized for the first as a powerful green and energy-efficient method for the synthesis of this nanoporous metal-organic framework. Certain ratio of metal ion and organic linkers were held to improve the quality of nanostructures. Cu2(BDC)2(BPY) were characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and Brunauer-Emmett-Teller (BET) surface area analysis.
Khosravi, Armaqan,Mokhtari, Javad,Naimi-Jamal, Mohammad Reza,Tahmasebi, Sharareh,Panahi, Leila
p. 46022 - 46027
(2017/10/10)

A method for preparing aromatic amine derivative
The invention discloses a preparation method of a diarylamine ramification. The preparation method comprises the following steps: dissolving a phenylamine ramification, a phenylhydrazine ramification, a metal phthalocyanine ramification and a copper salt into a solvent, and reacting at -10 to 40 DEG C to obtain the diarylamine ramification. According to the preparation method, the phenylamine ramification and the phenylhydrazine ramification are taken as starting materials, so that raw materials are easy to obtain and plenty in variety; a product obtained by utilizing the method is plenty in type, can not only be directly used, but also be used for other further reactions; and no additive is required to be added. The preparation method disclosed by the invention has the advantages of short synthetic route, moderation in reaction condition, simple reaction operation and post-processing process, high yield and suitability for large-scale production.
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Paragraph 0146-0149

(2016/10/08)

CoPc/Cu(OAc)2-catalyzed N-arylation of amines with arylhydrazines leading to N-aryl amines
The N-arylation of amines with arylhydrazines has been developed, achieving the selective cross-coupling of aryl radicals with amines to form N-aryl amines. The reaction uses air as an oxidant, CoPc and Cu(OAc)2as catalysts. The reaction proceeds under mild conditions in air through a relay process, arylhydrazines are oxidized to aryldiazenes by CoPc, further oxidized to aryl radicals by air (O2), which are trapped by Cu(OAc)2–amine complex, followed by reduction–elimination reaction to form N-aryl amines. Arylamines and arylhydrazines give the highest yields, but N-aryl-N-alkylamines and N-alkylamines can be used as well.
Sun, Wang-Bin,Zhang, Pei-Zhi,Jiang, Tao,Li, Cheng-Kun,An, Li-Tao,Shoberu, Adedamola,Zou, Jian-Ping
p. 6477 - 6483
(2016/09/23)

Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem
The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.
Vantourout, Julien C.,Law, Robert P.,Isidro-Llobet, Albert,Atkinson, Stephen J.,Watson, Allan J. B.
p. 3942 - 3950
(2016/05/24)

A facile and practical copper diacetate mediated, ligand free C-N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes
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.
Jadhav,Pardeshi
p. 14531 - 14537
(2016/02/19)

A quick Chan-Lam C-N and C-S cross coupling at room temperature in the presence of square pyramidal [Cu(DMAP)4I]I as a catalyst
A rapid and efficient protocol for C-N and C-S cross coupling has been developed using a new square pyramidal copper complex, [Cu(DMAP)4I]I. The complex was successfully synthesized via a disproportionation reaction of CuI and DMAP in DMSO. The catalytic activity of the complex was found to be excellent for Chan-Lam coupling reaction between aryl boronic acid and amine, amide, azide or thiol. The reaction could be carried out in the presence of only 2 mol% of the copper catalyst in methanol at room temperature within a short time.
Roy, Subhasish,Sarma, Manas Jyoti,Kashyap, Bishwapran,Phukan, Prodeep
supporting information
p. 1170 - 1173
(2016/01/15)

An electroluminescent compound and an electroluminescent device comprising the same
The present invention relates to an organic light emitting compound adopted to an organic electroluminescent device. The organic light emitting compound is represented by chemical formula 1 or chemical formula 2. In the case of adopting the organic light emitting compound as a phosphorescence host compound in a hole transport functional layer or a luminous layer, an organic electroluminescent device having excellent luminous characteristics such as operating voltage, brightness, long lifespan, etc.
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Paragraph 0289-0291; 0760-0762

(2016/10/10)

Anchoring of Pd(ii) complex in functionalized MCM-41 as an efficient and recoverable novel nano catalyst in C-C, C-O and C-N coupling reactions using Ph3SnCl
Anchored palladium(ii) in functionalized MCM-41 mesoporous silica was prepared and used as an efficient, recoverable and thermally stable heterogeneous nano catalyst for C-C, C-O and C-N bond formation in cross-coupling reactions in the presence of Ph3SnCl. MCM-41 was prepared trough hydrothermal synthesis using tetraethyl orthosilicate (Si(OC2H5)4) as silica source and cetyltrimethylammonium bromide (CTAB) as a template. The structure of functionalized MCM-41 was studied by FT-IR, XRD, SEM, TEM, TGA, EDS, ICP and BET techniques.
Ghorbani-Choghamarani, Arash,Nikpour, Farzad,Ghorbani, Farshid,Havasi, Forugh
p. 33212 - 33220
(2015/04/27)

Visible-Light-Mediated Chan-Lam Coupling Reactions of Aryl Boronic Acids and Aniline Derivatives
The copper(II)-catalyzed aerobic oxidative coupling reaction between aryl boronic acids and aniline derivatives was found to be improved significantly under visible-light-mediated photoredox catalysis. The substrate scope of this oxidative Chan-Lam reaction was thus expanded to include electron-deficient aryl boronic acids as viable starting materials. Two are better than one: The copper(II)-catalyzed aerobic oxidative coupling reaction between aryl boronic acids and anilines is significantly improved by the addition of visible-light-mediated photoredox catalysts. The substrate scope of this Chan-Lam reaction was thus expanded to include electron-deficient aryl boronic acids.
Yoo, Woo-Jin,Tsukamoto, Tatsuhiro,Kobayashi, Shu
supporting information
p. 6587 - 6590
(2015/06/02)

One-pot synthesis of n-aryl-nicotinamides and diarylamines based on a tunable smiles rearrangement
A one-pot Smiles rearrangement has been developed as a useful protocol for the straightforward synthesis of diverse N-aryl-nicotinamides. This method also provides chemoselective access toward diarylamines based on the different substitutions of the amide group. The potential application of the transformation is exemplified by the synthesis of an on-market succinate dehydrogenase inhibitor, boscalid. A substituent-mediated Smiles rearrangement to N-aryl-nicotinamides and diarylamines has been developed. In addition to the wide range of heterocyclic building blocks, the one-pot process also provides an efficient access to an on-market fungicide, boscalid.
Liu, Shihui,Zhu, Shaofan,Wu, Ying,Gao, Jiayu,Qian, Pengfei,Hu, Yanwei,Shi, Linsen,Chen, Shaohua,Zhang, Shilei,Zhang, Yinan
supporting information
p. 3048 - 3052
(2015/05/13)

Aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide mediated by anthraquinone-2-carboxylic acid
We developed the aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide in the presence of anthraquinone-2-carboxylic acid under visible light irradiation.
Tanaka, Masanori,Kamito, Yuji,Lei, Cui,Tada, Norihiro,Itoh, Akichika
p. 5886 - 5888
(2015/11/02)

Catalytic activity and antibacterial properties of nanopolymer-supported copper complex for C-N coupling reactions of amines and nitrogen-containing heterocycles with aryl halides
This paper reports on the antibacterial properties and application of nanopolymer-supported copper complex for the ligand-free C-N coupling reactions of amines and nitrogen-containing heterocycles with aryl halides. This method has the advantages of high yields, simple methodology, and easy workup. The catalyst can be recovered by simple filtration from the reaction mixture and reused several times without significant loss of catalytic activity.
Nasrollahzadeh, Mahmoud,Zahraei, Ali,Pourbasheer, Eslam
p. 1329 - 1334
(2015/08/18)