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
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
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
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
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
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
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
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
Herein,we report rhodium catalyzed N-arylation via addition of arylboronic acids to electron-deficientα-iminoesters which can be prepared in high efficiency by using easily accessible B-carbonyl esters.The reaction i...Herein,we report rhodium catalyzed N-arylation via addition of arylboronic acids to electron-deficientα-iminoesters which can be prepared in high efficiency by using easily accessible B-carbonyl esters.The reaction is highly regiospecific to achieve the N-aryl addition efficiently with up to 99%yield under mild conditions.The corresponding product can be further efficiently converted into indoles andaseries of other important building blocks.展开更多
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
Four inexpensive and air-/moisture-stable pyrrolecarbaldiminato-Cu complexes 1-4 were synthesized and evaluated to be a novel class of catalysts for the N-arylation of imidazoles with aryl halides. A variety of aryl i...Four inexpensive and air-/moisture-stable pyrrolecarbaldiminato-Cu complexes 1-4 were synthesized and evaluated to be a novel class of catalysts for the N-arylation of imidazoles with aryl halides. A variety of aryl iodides, bromides and activated aryl chlorides underwent the coupling with imidazoles, promoted by the catalyst 4, in moderate to good yields without the protection by an inert gas.展开更多
A general and efficient Cu（II）-catalyzed cross-coupling method is reported for the preparation of acyclic tertiary amides. Generally moderate to excellent yields and functional group tolerance were obtained with sec...A general and efficient Cu（II）-catalyzed cross-coupling method is reported for the preparation of acyclic tertiary amides. Generally moderate to excellent yields and functional group tolerance were obtained with secondary acyclic amides and aryl halides as substrates in toluene.展开更多
A combination of CuSO4/dimethylglyoxime was found to be an efficient and inexpensive catalyst system for N-arylation of imidazole and benzimidazole with aryl halides and heteroaryl halides in water, providing the corr...A combination of CuSO4/dimethylglyoxime was found to be an efficient and inexpensive catalyst system for N-arylation of imidazole and benzimidazole with aryl halides and heteroaryl halides in water, providing the corresponding products in moderate to good yields.展开更多
A simple and efficient C--N cross-coupling method of aryl halides with various heterocycles was reported, by using 10 tool% of CuI as catalyst and 1.2 equiv. Nail as base. Aryl iodides, aryl bromides and many substitu...A simple and efficient C--N cross-coupling method of aryl halides with various heterocycles was reported, by using 10 tool% of CuI as catalyst and 1.2 equiv. Nail as base. Aryl iodides, aryl bromides and many substituted atyl chlorides could efficiently react with heterocycles, providing variety of N-arylated products in good to excellent yields. The ligand-free catalyst system was stable in air and could be readily reused.展开更多
An efficient approach for the synthesis of N-arylated amides was developed via copper(Ⅱ) triflate-catalyzed direct oxidation of(aryl)methylamines to primary arylamides by air and subsequent N-arylation by diaryliodon...An efficient approach for the synthesis of N-arylated amides was developed via copper(Ⅱ) triflate-catalyzed direct oxidation of(aryl)methylamines to primary arylamides by air and subsequent N-arylation by diaryliodonium salts. Various substituted benzylamines could be applied in the reaction, providing a series of N-arylated amides in moderate to good yields. This method showed convenient, practical, and environment friendly advantages.展开更多
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
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
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
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
基金supported by the Natural Science Foundation of Zhejiang Province(No.Y407240).
文摘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.
基金National Natural Science Foundation of China(Grant No. 20802005 and 20972007)the National Basic Research Program of China (973 Program, Grant No. 2010CB833200)
文摘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.
文摘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%）.
文摘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.
基金supported by the National Natural Science Foundation of China (No.21102036)Plan for Scientific Innovation Talent of Henan University of Technology (No.11CXRC02)startup fund from HAUT (No.2010BS042)
文摘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.
基金supported fnancially by the National Basic Research Program of China(973 Program,No.2012CB722603)the Start-Up Foundation for Young Scientists of Shihezi University(Nos.RCZX201012,RCZX201014,RCZX201015)
文摘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.
基金supported by the Natural Science Foundation of China(91645115 and 21473003)High-level talents funding project of Hebei(CL201601,E2016100015)science technology research and development guidance program project of Baoding City(No.16ZF027)
文摘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.
基金financial support of this work by the National Basic Research Program of China (973 Program, No. 2012CB722603)the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT1161)+1 种基金the National Natural Science Foundation of China (No. 21103114)the Doctor Foundation of Xinjiang Bingtuan (No. 2012BB010)
文摘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%.
基金financial support from the Natural Science Foundation of Shanghai(20zR1405500).
文摘Herein,we report rhodium catalyzed N-arylation via addition of arylboronic acids to electron-deficientα-iminoesters which can be prepared in high efficiency by using easily accessible B-carbonyl esters.The reaction is highly regiospecific to achieve the N-aryl addition efficiently with up to 99%yield under mild conditions.The corresponding product can be further efficiently converted into indoles andaseries of other important building blocks.
基金supported by Shenzhen Science and Technology Research(Nos.JSGG20201103153807021,GXWD20220811173736002,KCXFZ20230731094904009)the Fundamental Research Funds for the Central Universities,Sun Yat-sen University(No.24qnpy060)+2 种基金Natural Science Foundation of Guangdong Province(No.2021A1515110366)National Natural Science Foundation of China(Nos.22302048,82204231,22275146)Shenzhen Key Laboratory of Advanced Functional Carbon Materials Research and Comprehensive Application。
文摘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).
文摘Four inexpensive and air-/moisture-stable pyrrolecarbaldiminato-Cu complexes 1-4 were synthesized and evaluated to be a novel class of catalysts for the N-arylation of imidazoles with aryl halides. A variety of aryl iodides, bromides and activated aryl chlorides underwent the coupling with imidazoles, promoted by the catalyst 4, in moderate to good yields without the protection by an inert gas.
基金We gratefully thank the National Natural Science Foundation of China （No. 31071720） for generous fi- nancial support.
文摘A general and efficient Cu（II）-catalyzed cross-coupling method is reported for the preparation of acyclic tertiary amides. Generally moderate to excellent yields and functional group tolerance were obtained with secondary acyclic amides and aryl halides as substrates in toluene.
文摘A combination of CuSO4/dimethylglyoxime was found to be an efficient and inexpensive catalyst system for N-arylation of imidazole and benzimidazole with aryl halides and heteroaryl halides in water, providing the corresponding products in moderate to good yields.
基金This work was supported by the National Natural Science Foundation of China （No. 20802049）.
文摘A simple and efficient C--N cross-coupling method of aryl halides with various heterocycles was reported, by using 10 tool% of CuI as catalyst and 1.2 equiv. Nail as base. Aryl iodides, aryl bromides and many substituted atyl chlorides could efficiently react with heterocycles, providing variety of N-arylated products in good to excellent yields. The ligand-free catalyst system was stable in air and could be readily reused.
基金This work was financially supported by the National Nature Science Foundation of China(21272069,20672035)the Fundamental Reearch Funds for the Central Universities and Key Laboratory of Organofluorine Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences.
文摘An efficient approach for the synthesis of N-arylated amides was developed via copper(Ⅱ) triflate-catalyzed direct oxidation of(aryl)methylamines to primary arylamides by air and subsequent N-arylation by diaryliodonium salts. Various substituted benzylamines could be applied in the reaction, providing a series of N-arylated amides in moderate to good yields. This method showed convenient, practical, and environment friendly advantages.
基金the financial support from National Natural Science Foundation of China(NSFC,Nos.22175081 and 21833005)Beijing National Laboratory for Molecular Sciences(No.BNLM202010)+1 种基金State Key Laboratory of Physical Chemistry of Solid Surfaces(No.202108)Guangdong Provincial Key Laboratory of Catalysis(No.20210701)。
文摘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.
基金Support of this work by the National Natural Science Foundation of China(21573016)is gratefully acknowledged.
文摘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.
文摘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.
基金the National Natural Science Foundation of China (No. 21262020)the Science and Technology Planning Project of Yunnan Province (No. KKSY201207140)+1 种基金the Natural Science Foundation of Yunnan Education Department (No. 09Y0081)the Analysis and Measurement Foundation of Kunming University of Science and Technology (No. 20130560) for their financial supports
文摘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.
