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Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles
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作者 Chengyao Zhao Jingyuan Liao +4 位作者 Yuxiang Zhu Yiying Zhang Lianjie Zhai Junrong Huang Hengzhi You 《Chinese Chemical Letters》 2025年第6期404-408,共5页
The significance of axial chiral compounds in asymmetric organic catalysis,functional materials,and pharmaceutical useful molecules has encouraged advancements in the atroposelective synthesis of such compounds.Herein... The significance of axial chiral compounds in asymmetric organic catalysis,functional materials,and pharmaceutical useful molecules has encouraged advancements in the atroposelective synthesis of such compounds.Herein,we report the first atroposelective construction of axially chiral N-aryl benzimidazoles catalyzed by a polymer-supported chiral phosphoric acid.A varied library of atropisomers has been synthesized in 30%-96%yield with 58%-98%enantiomeric excess(ee)under a straightforward reaction setup(without the use of molecular sieves).Notably,even after 12 cycles,the immobilized catalyst maintained its reactivity and selectivity(TON>540). 展开更多
关键词 Asymmetric catalysis Heterogeneous catalysis Chiral phosphoric acid Atroposelective synthesis n-aryl benzimidazoles
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N-Arylation of azaheterocycles with aryl and heteroaryl halides catalyzed by iminodiacetic acid resin-chelated copper complex 被引量:5
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作者 Wu, Xiang Mei Wang, Yan 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第1期51-54,共4页
Iminodiacetic acid resin-chelated copper(Ⅱ) complex is effective in cross-coupling reactions between azaheterocycles and aryl or heteroaryl halides,providing N-arylated products in good to excellent yields.The copper... Iminodiacetic acid resin-chelated copper(Ⅱ) complex is effective in cross-coupling reactions between azaheterocycles and aryl or heteroaryl halides,providing N-arylated products in good to excellent yields.The copper catalyst is air stable and can be readily recovered and reused with minimal loss of activity for three runs. 展开更多
关键词 n-arylATION COPPER Azaheterocycle Iminodiacetic acid resin
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CuI-catalyst N-arylation of 4-iodotryptophan derivatives: effort toward the total synthesis of indolactam V
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作者 江静倩 徐正仁 贾彦兴 《Journal of Chinese Pharmaceutical Sciences》 CAS 2012年第2期113-123,共11页
Efforts toward the total synthesis of indolactam V via CuI-mediated inter- and intra-molecular N-arylation of 4-iodotryptophan derivatives for the introduction of 4-valine moiety from natural L-valine are described. M... Efforts toward the total synthesis of indolactam V via CuI-mediated inter- and intra-molecular N-arylation of 4-iodotryptophan derivatives for the introduction of 4-valine moiety from natural L-valine are described. Meanwhile, the efficient synthesis of several pyrroloquinoline derivatives by taking advantage of the CuI-catalyzed intramolecular N-arylation reaction of 4-iodotryptophan is disclosed. 展开更多
关键词 Intermolecular n-arylation CuI catalyst Pyrroloquinoline derivatives Indolactam V
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Practical copper-catalyzed N-arylation of amines with 20% aqueous solution of n-Bu_4NOH 被引量:3
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作者 Hamidreza Molaei Mohammad Mehdi Ghanbari 《Chinese Chemical Letters》 SCIE CAS CSCD 2012年第3期301-304,共4页
N-Arylation of a wide variety of amines with phenylboronic acid catalyzed by copper acetate under 20%aqueous solution of n-Bu_4NOH was accomplished in good to excellent yields(up to 92%) and substrate conversions(u... N-Arylation of a wide variety of amines with phenylboronic acid catalyzed by copper acetate under 20%aqueous solution of n-Bu_4NOH was accomplished in good to excellent yields(up to 92%) and substrate conversions(up to 96%). 展开更多
关键词 COPPER-CATALYZED n-arylATION Phenylboronic acid AMINES
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A bifunctional and recyclable catalyst:Amine and ionic liquid grafting on MOFs for the one-pot synthesis of N-aryl oxazolidin-2-ones 被引量:3
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作者 Siying Chong Tongtong Wang +4 位作者 Haijun Zhong Lingfei Xu Hailong Xu Zhongwu Lv Min Ji 《Green Energy & Environment》 SCIE CSCD 2020年第2期154-165,共12页
A bifunctional heterogeneous catalyst was designed and synthesized,denoted DMEDA/IL–NH2-MIL-101.The structure and physical-chemical characterization of DMEDA/IL–NH2-MIL-101 and its precursors were characterized by S... A bifunctional heterogeneous catalyst was designed and synthesized,denoted DMEDA/IL–NH2-MIL-101.The structure and physical-chemical characterization of DMEDA/IL–NH2-MIL-101 and its precursors were characterized by SEM,N2 adsorption-desorption,XPS,FT-IR,PXRD,elemental analysis,and TGA techniques.The date showed that the two catalytic components of N,N-dimethylethylenediamine(DMEDA)and 1-butyl-3-methylimidazolium bromide(BmimBr)were chemically immobilized in NH2-MIL-101 nanocages.The amine of DMEDA was grafted onto carrier NH2-MIL-101 by N–Cr coordinate covalent bonds and the ionic liquid of BmimBr(IL(Br-))was anchored in the NH2-MIL-101 nanocages by'ship-in-a-bottle'method,in which the amidogen of NH2-MIL-101 condensed with N,N-carbonyldiimidazole(CDI)firstly,and then alkylated with 1-bromo butane.This novel heterogeneous catalyst with two different active sites can efficiently catalyze the synthesis of N-aryl oxazolidin-2-ones from carbon dioxide(CO2),epoxides,and anilines in one-pot under mild solvent-free conditions.It not only showed good stability and recoverability after five cycles but also exhibited shape selectivity for the substrate due to the synergic catalysis of amine,ionic liquid,and NH2-MIL-101.This novel bifunctional material is a promising solid catalyst for the green synthesis of N-aryl oxazolidin-2-ones. 展开更多
关键词 Metal-organic frameworks Ionic liquid immobilization n-aryl oxazolidin-2-ones One-pot synthesis Bifunctional heterogeneous catalyst
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CuI/Proline-catalyzed N-Arylation of Nitrogen Heterocycles 被引量:2
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作者 Wei DENG Ye Feng WANG Chen ZHANG Lei LIU Qing Xiang GUO 《Chinese Chemical Letters》 SCIE CAS CSCD 2006年第3期313-316,共4页
Ma's CuI/proline procedure for the catalytic cross coupling between nitrogen heterocycles and aryl halides was markedly improved. The key finding was that K3PO4 was a much better base than K2CO3 for the reaction. Wit... Ma's CuI/proline procedure for the catalytic cross coupling between nitrogen heterocycles and aryl halides was markedly improved. The key finding was that K3PO4 was a much better base than K2CO3 for the reaction. With this new reaction condition the cross coupling with aryl iodides could be accomplished in 1,4-dioxane instead of DMSO. This reactin also could be carried out in DMF. Furthermore, the coupling yields under the new conditions are usually higher than in Ma's original methods. 展开更多
关键词 Cross coupling reaction CUI n-arylATION nitrogen heterocycle proline.
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Copper-catalyzed N-arylation of 2-arylindoles with aryl halides 被引量:2
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作者 Wei Liu Li-Ya Han +2 位作者 Rui-Li Liu Li-Ge Xu Yan-Lan Bi 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第9期1240-1243,共4页
10 mol% Cul combined with the DMEDA ligand can efficiently catalyze the N-arylation of 2-arylindoles with aryl iodides and aryl bromides in good to excellent yields. The aryl halides bearing electron-rich or electron-... 10 mol% Cul combined with the DMEDA ligand can efficiently catalyze the N-arylation of 2-arylindoles with aryl iodides and aryl bromides in good to excellent yields. The aryl halides bearing electron-rich or electron-deficient functional groups can be well tolerated under this mild reaction conditions. 展开更多
关键词 2-Arylindoles Aryl halides n-arylATION COPPER
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Synthesis of N-arylquinolone derivatives bearing 2-thiophenoxyquinolines and their antimicrobial evaluation 被引量:1
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作者 Mehul B.Kanani Manish P.Patel 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第7期1073-1076,共4页
A new series of 2-thiophenoxyquinolines based trifluoromethyl substituted N-aryl quinolone derivatives 8a-f and 9a-f have been synthesized via a one-pot multicomponent reaction. In vitro antimicrobial activity of the ... A new series of 2-thiophenoxyquinolines based trifluoromethyl substituted N-aryl quinolone derivatives 8a-f and 9a-f have been synthesized via a one-pot multicomponent reaction. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains. Compounds 8c, 9c and 9e exhibited comparable antimicrobial activity to first line drugs. 展开更多
关键词 2-Thiophenoxyquinoline TRIFLUOROMETHYL n-aryl quinolone Antimicrobial activity
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N-Aryl diketopyrrolopyrrole derivatives towards organic optical and electronic materials 被引量:1
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作者 Jinqiu Meng Nan Luo +3 位作者 Guanxin Zhang Xiangfeng Shao Zitong Liu Deqing Zhang 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第6期157-163,共7页
Diketopyrrolopyrrole(DPP)and related derivatives have drawn great attention due to their applications in organic optical/electronic materials.Progress in these materials is associated with developments in the synthese... Diketopyrrolopyrrole(DPP)and related derivatives have drawn great attention due to their applications in organic optical/electronic materials.Progress in these materials is associated with developments in the syntheses of the DPP family.Chemical modification of DPP at nitrogen atom,including N-alkylation and N-arylation,is an effective strategy to improve its physical and chemical properties,such as solubility,optical and semiconducting properties.However,N-arylation of DPPs remains challenging compared to the easily accessible N-alkylation.Herein,the synthesis of N-aryl DPP derivatives and correlatedπ-expanded DPPs are summarized,and their optical/electronic properties are introduced.The future perspectives of N-aryl DPP derivatives are also discussed. 展开更多
关键词 DIKETOPYRROLOPYRROLE n-arylATION π-expanded derivatives Organic optical material Organic electronic material
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A mild and simple synthesis of N-aryl substituted toluenesulfamides under solvent-free conditions 被引量:1
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作者 ZHAO Na WANG Yu-lu 《合成化学》 CAS CSCD 2004年第z1期73-73,共1页
关键词 grinding solvent-free n-aryl SUBSTITUTED toluenesulfamides
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Tetrazole-1-acetic acid as a ligand for copper-catalyzed N-arylation of imidazoles with aryl iodides under mild conditions 被引量:3
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作者 Feng-Tian Wu Ping Liu +2 位作者 Xiao-Wei Ma Jian-Wei Xie Bin Dai 《Chinese Chemical Letters》 SCIE CAS CSCD 2013年第10期893-896,共4页
Tetrazole-l-acetic acid was found to serve as a superior ligand for Cul-catalyzed N-arylation of imidazoles with aryl iodides under a low catalyst loading (5 mol% of Cul). A variety of aryl iodides could he aminated... Tetrazole-l-acetic acid was found to serve as a superior ligand for Cul-catalyzed N-arylation of imidazoles with aryl iodides under a low catalyst loading (5 mol% of Cul). A variety of aryl iodides could he aminated to provide the N-arylated products in good to excellent yields without the need of an inert atmosphere. 展开更多
关键词 Tetrazole-l-acetic acid n-arylation Imidazoles Copper Aryl iodides
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One-step synthesis of carbon-supported copper nanoparticles from biomass for N-arylation of pyrazole 被引量:2
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作者 Wenjing Li Yongjun Gao +2 位作者 Pei Tang Yao Xu Ding Ma 《Journal of Energy Chemistry》 SCIE EI CAS CSCD 2018年第3期859-865,共7页
Carbon-supported copper catalyst was prepared for the first time in one-step with copper nitrate and corn stalk through calcination under different temperatures. Uniformly dispersed nanoparticles were obtained and wer... Carbon-supported copper catalyst was prepared for the first time in one-step with copper nitrate and corn stalk through calcination under different temperatures. Uniformly dispersed nanoparticles were obtained and were identified to be Cu(0) and Cu(Ⅰ) in XRD patterns. Excellent catalytic activity and selectivity were achieved in the N-arylation of pyrazole under ligand and protection gas free conditions. About90.4% of product yield was achieved with only 0.5 mol% of copper catalyst(Cu-C-300), which was considerably more efficient than previous reports. XPS results suggested that the N-arylation of pyrazole activity was closely related to the surface Cu(Ⅰ) species. 展开更多
关键词 Corn stalk Carbon-supported copper n-arylation Ligand-free
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One-pot synthesis of N-aryl propargylamine from aromatic boronic acid,aqueous ammonia,and propargyl bromide under microwave-assisted conditions 被引量:2
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作者 Yu-Bo Jiang Wen-Sheng Zhang +2 位作者 Hui-Ling Cheng Yu-Qi Liu Rui Yang 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第5期779-782,共4页
A facile,one-pot synthesis of N-aryl propargylamine from aromatic boronic acid,aqueous ammonia,and propargyl bromide has been achieved under microwave-assisted conditions.The reactions can be smoothly completed within... A facile,one-pot synthesis of N-aryl propargylamine from aromatic boronic acid,aqueous ammonia,and propargyl bromide has been achieved under microwave-assisted conditions.The reactions can be smoothly completed within a total 10 min through a two-step procedure,including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide. 展开更多
关键词 One-pot Microwave n-aryl propargylamine Aromatic boronic acid Aqueous ammonia Propargyl bromide
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Electrochemical C-H/N-H cross-coupling of 2-phenylindolizines with phenothiazines to synthesize novel N-aryl phenothiazine derivatives
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作者 Chenglong Feng Xin Liu +2 位作者 Yuanbin She Zhenlu Shen Meichao Li 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第6期306-309,共4页
A facile and elegant method for synthesis of novel N-aryl phenothiazine derivatives from 2-phenylindolizines and phenothiazines through direct electrochemical oxidation has been developed.This approach was performed s... A facile and elegant method for synthesis of novel N-aryl phenothiazine derivatives from 2-phenylindolizines and phenothiazines through direct electrochemical oxidation has been developed.This approach was performed smoothly at room temperature without external oxidant and catalyst.Cyclic voltammetry and in situ FTIR techniques were applied to analyze the cross-coupling process of phenothiazines and 2-phenylindolizines,which helped to select the appropriate reaction potential.Under the optimized conditions,a broad range of substrates were well tolerated,affording the desired products in moderate to excellent isolated yields(up to 91%)with high regioselectivity.Meanwhile,a plausible mechanism involving a radical pathway has been proposed. 展开更多
关键词 n-aryl phenothiazine derivatives Electrochemical oxidation 2-Phenylindolizines PHENOTHIAZINES CROSS-COUPLING
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Dimethyl sulfoxide-aided copper(0)-catalyzed intramolecular decarbonylative rearrangement of N-aryl isatins leading to acridones
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作者 Hao Wu Nana Ma +1 位作者 Mengxiao Song Guisheng Zhang 《Chinese Chemical Letters》 SCIE CAS CSCD 2020年第6期1580-1583,共4页
Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide(DMSO)under air atmosphere and additive-fr... Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide(DMSO)under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields.This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C-N bond,CO extrusion,Cu migration,reductive elimination and DMSO-aided proton migration processes,involving multiple types of bond cleavage and formation in a single chemical step. 展开更多
关键词 Cu(0)-catalyzed decarbonylation Decarbonylative rearrangements DMSO-aided reactions n-aryl isatins ACRIDONES
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3-(Diphenylphosphino)propanoic acid: An efficient ligand for the Cu-catalyzed N-arylation of imidazoles and 1H-pyrazole with aryl halides
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作者 Ya-Shuai Liu Yan Liu +3 位作者 Xiao-Wei Ma Ping Liu Jian-Wei Xie Bin Dai 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第5期775-778,共4页
3-(Diphenylphosphino)propanoic acid(L2) has proved to be an efficient ligand for the copper-catalyzed C–N coupling reactions.N-arylation of imidazoles with aryl iodides catalyzed by CuCl/L2 was smoothly carried o... 3-(Diphenylphosphino)propanoic acid(L2) has proved to be an efficient ligand for the copper-catalyzed C–N coupling reactions.N-arylation of imidazoles with aryl iodides catalyzed by CuCl/L2 was smoothly carried out in DMSO at 100 8C with a yield up to 98%.N-arylation of 1H-pyrazole with aryl iodides and bromides catalyzed by Cu(OAc)2/L2 in 1 4-dioxane also gave the corresponding products with yields of40%–98%. 展开更多
关键词 Cu catalyzed C–N coupling n-arylation P O ligands
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Selective arylation/annulation cascade reactions of 2-alkynylanilines with diaryliodonium salts
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作者 段英 杨艳良 +1 位作者 戴晓玉 李东密 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2016年第11期1837-1840,共4页
An efficient Cu catalyzed selective arylation/annulation cascade reaction of 2-alkynylanilines with diaryliodonium salts was developed.This reaction was selective to N-arylation instead of C-arylation,which provides a... An efficient Cu catalyzed selective arylation/annulation cascade reaction of 2-alkynylanilines with diaryliodonium salts was developed.This reaction was selective to N-arylation instead of C-arylation,which provides a simple synthetic method for N-aryl indoles. 展开更多
关键词 Selective arylation ANNULATION Diaryliodonium salt 2-Alkynylaniline n-aryl indole Cascade reaction
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Microwave-assisted chemoselective copper-catalyzed amination of o-chloro and o-bromobenzoic acids using aromatic amines under solvent free conditions 被引量:2
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作者 Yaghoub Sarrafi Manijeh Mohadeszadeh Kamal Alimohammadi 《Chinese Chemical Letters》 SCIE CAS CSCD 2009年第7期784-788,共5页
Copper-catalyzed synthesis of N-aryl anthranilic acid derivatives using effective amination of 2-chloro and 2-bromobenzoic acid under microwave irradiation is reported. Some of the advantages of this method are high c... Copper-catalyzed synthesis of N-aryl anthranilic acid derivatives using effective amination of 2-chloro and 2-bromobenzoic acid under microwave irradiation is reported. Some of the advantages of this method are high chemoselectivity, short reaction times, ease of work up procedure and elimination of the need for acid protection. 2009 Published by Elsevier B.V. on behalf of Chinese Chemical Society. 展开更多
关键词 MICROWAVE-ASSISTED COPPER-CATALYZED Solvent free AMINATION n-aryl anthranilic acid
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Popping of g-C_3N_4 mixed with cupric nitrate: Facile synthesis of Cu-based catalyst for construction of C-N bond 被引量:1
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作者 Shaoyu Yuan Penglei Cui +3 位作者 Yunrui Zhang Hong Zhang Li Huo Yongjun Gao 《Green Energy & Environment》 SCIE 2018年第4期368-374,共7页
A novel strategy to synthesize copper-based nanoparticles supported on carbon nitride(C3 N4) was developed by popping of mixture containing C3 N4 and cupric nitrate. Characterizations such as X-ray photoelectron spect... A novel strategy to synthesize copper-based nanoparticles supported on carbon nitride(C3 N4) was developed by popping of mixture containing C3 N4 and cupric nitrate. Characterizations such as X-ray photoelectron spectroscopy(XPS) and X-ray diffraction(XRD) indicate that the structure of g-C3 N4 maintained although a popping process occurred. High resolution transmission electronic microscopy(HRTEM) characterization illustrated that copper-based nanoparticles with diameter of < 1 nm were well distributed on g-C3 N4. This kind of copper catalyst exhibits high catalytic activity and selectivity in arylation of pyrazole, a simple and effect strategy to construct C-N bond in organic chemistry.According to the results of control experiments and characterizations, cuprous oxide should be the catalytic active phase in the supported coperbased catalyst. 展开更多
关键词 C-N coupling n-arylATION Carbon NITRIDE Catalysis COPPER-BASED catalyst
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Salen-Cu(II) Complex Catalyzed <i>N</i>-Arylation of Imidazoles under Mild Conditions 被引量:2
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作者 Yan Liu Qin Zhang +4 位作者 Xiaowei Ma Ping Liu Jianwei Xie Bin Dai Zhiyong Liu 《International Journal of Organic Chemistry》 2013年第3期185-189,共5页
Three inexpensive and air-/moisture-stable Salen-Cu complexes 1-3 were evaluated to be a novel class of catalysts for the N-arylation of imidazoles with aryl halides. A variety of aryl iodides, bromides underwent the ... Three inexpensive and air-/moisture-stable Salen-Cu complexes 1-3 were evaluated to be a novel class of catalysts for the N-arylation of imidazoles with aryl halides. A variety of aryl iodides, bromides underwent the coupling with imida-zoles, promoted by the complex 3, in moderate to excellent yields without the protection by an inert gas. 展开更多
关键词 Salen-Cu COMPLEX n-arylATION Imidazole CATALYZE
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