共查询到20条相似文献,搜索用时 15 毫秒
1.
Dr. Johanne Ling Dr. Antoine Bruneau-Voisine Dr. Guillaume Journot Prof. Gwilherm Evano 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(44):e202201356
A general copper-catalyzed carbonylative cross-coupling between amines and alkyl iodides is reported. Using a simple combination of catalytic amounts of copper(I) chloride and N,N,N’,N”,N”-pentamethyldiethylenetriamine in the presence of sodium hydroxide under carbon monoxide pressure, a broad range of alkyl iodides and amines can be efficiently coupled to the corresponding amides that are obtained in good to excellent yields. Notable features of this process – the first one relying on a base metal catalyst – include the availability and low cost of the catalytic system, its successful use with primary, secondary, tertiary alkyl iodides and all classes of amines – with no or limited competing nucleophilic substitution without CO incorporation – as well as its efficiency with complex alkyl iodides and amines. Mechanistic studies demonstrated that a radical pathway is operative and the key role of CO. 相似文献
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Alisa D. Kharlamova Anton S. Abel Alexei D. Averin Olga A. Maloshitskaya Vitaly A. Roznyatovskiy Evgenii N. Savelyev Boris S. Orlinson Ivan A. Novakov Irina P. Beletskaya 《Molecules (Basel, Switzerland)》2021,26(7)
N-heteroaryl substituted adamantane-containing amines are of substantial interest for their perspective antiviral and psychotherapeutic activities. Chlorine atom at alpha-position of N-heterocycles has been substituted by the amino group using convenient nucleophilic substitution reactions with a series of adamantylalkylamines. The prototropic equilibrium in these compounds was studied using NMR spectroscopy. The introduction of the second amino substituent in 4-amino-6-chloropyrimidine, 2-amino-chloropyrazine, and 1-amino-3-chloroisoquinoline was achieved using Pd(0) catalysis. 相似文献
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Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents
NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols. 相似文献
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铜催化的芳环C—H键直接芳基化反应已成为一种合成联芳烃化合物的重要手段,近年来一直是有机化学和催化化学的研究热点和难点之一.按照参与反应的底物或成键模式的不同对近年来铜催化的芳环C—H键直接芳基化反应的研究进展进行了综述. 相似文献
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Shishkin V. N. Esina I. V. Lapin K. K. Butin K. P. 《Russian Journal of Organic Chemistry》2002,38(3):374-377
Polybromobenzenes C6Br5X (X = Br, F, CN, NO2) react with primary amines (methylamine and cyclohexylamine) to give nucleophilic substitution products; reactions of the same substrates with secondary amines (dimethylamine, diethylamine, piperidine, and morpholine) are accompanied by hydrodebromination processes. 相似文献
6.
A. P. Kozynchenko Yu. M. Volovenko F. S. Babichev V. K. Promonenkov 《Chemistry of Heterocyclic Compounds》1990,26(1):73-75
It has been shown that -chloroquinoxalines heteroarylate pyridin-2-yl and quinolin2-ylacetonitriles primarily at the methylene group. A method has been developed for synthesizing 1-R-2-amino-3-heteroarylpyrrolo[2,3-b]quinoxalines permitting the preparation of compounds containing the pyridine and quinoline nuclei.For Communication 2, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 85–87, January, 1990. 相似文献
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A simple, scalable, ligand-free, and metal-free protocol for arylation of amines and monoarylation of symmetrical diamines with diheteroaryl halides in the presence of brine solution has been developed. The protocol has broad structural applicability for chemoselective monoarylation of a wide variety of symmetrical, cyclic, and acyclic aliphatic diamines. The protocol is also applicable for selective arylation of aliphatic amine in the presence of aromatic amine. 相似文献
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Rahman Hosseinzadeh Mahmood Tajbakhsh Maryam Mohadjerani Parizad Rezaei Mohammad Alikarami 《合成通讯》2013,43(17):3023-3031
An efficient synthesis of diaryl ethers by the copper-catalyzed arylation of phenols with a variety of aryl iodide susing KF/Al2O3 as a suitable base and CuI and 1,3 diphenyl-1,3 propandione as the catalyst is described. 相似文献
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Miseon Choi Dr. Manish Kumar Mehra Prof. Chung Whan Lee 《European journal of organic chemistry》2023,26(4):e202201286
One-pot synthesis of various indolo[2,3-b]indoles has been accomplished from a copper-catalyzed transformation of easily accessible 2-(substituted-amino)aryl)(mesityl)iodonium salts and indole derivatives. Reaction offers great functional group toleration, providing a series of indolo[2,3-b]indole derivatives in good yields. Additionally, intramolecular cyclization of 2-(substituted-amino)aryl)(mesityl)iodonium salts in the presence of copper-catalyst provided direct access to benzoxazole derivatives. 相似文献
13.
Dr. Srimanta Manna Dr. Quentin Dherbassy Dr. Gregory J. P. Perry Prof. Dr. David J. Procter 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(12):4909-4912
An efficient, enantio- and diastereoselective, copper-catalyzed coupling of imines, 1,3-enynes, and diborons is reported. The process shows broad substrate scope and delivers complex, chiral homopropargyl amines; useful building blocks on the way to biologically-relevant compounds. In particular, functionalized homopropargyl amines bearing up to three contiguous stereocenters can be prepared in a single step. 相似文献
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《Tetrahedron letters》1988,29(32):3979-3982
Pd- and Ni-catalyzed reactions of methylenecyclopropanes with trimethylsilyl cyanide (1) give β-(cyanomethyl)allylsilanes and 1-(trimethylsilyl)methyl-1-cyclopropanecarbonitriles; the ratio of those depends on catalysts used and on the structure of substrates employed. 相似文献
17.
Regiospecific N‐Arylation of Aliphatic Amines under Mild and Metal‐Free Reaction Conditions
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Dr. Nibadita Purkait Gabriella Kervefors Erika Linde Prof. Berit Olofsson 《Angewandte Chemie (International ed. in English)》2018,57(35):11427-11431
A transition metal‐free N‐arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N‐alkyl anilines. The methodology is unprecedented among metal‐free methods in terms of amine scope, the ability to transfer both electron‐withdrawing and electron‐donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required. 相似文献
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A. D. Averin M. A. Ulanovskaya A. K. Buryak E. N. Savel’ev B. S. Orlinson I. A. Novakov I. P. Beletskaya 《Russian Journal of Organic Chemistry》2010,46(12):1790-1811
Palladium-catalyzed arylation of various (1-adamantyl)alkanamines with isomeric (ortho, meta, and para) bromochloro- and dibromobenzenes was studied. Optimal catalytic systems were found for the synthesis of mono- and diamination
products, and the dependences of their yields on the nature of the initial amine and dihalobenzene and on the amount of base
were examined. Side amination products were isolated, and paths of their formation were analyzed. 相似文献
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Xiaohong Li Bin Fu Qiao Zhang Xiuping Yuan Prof. Qian Zhang Prof. Tao Xiong Prof. Qian Zhang 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(51):23256-23260
A catalytic defluorinative hydroarylation of alkenes with polyfluoroarenes in the presence of dppbz-ligated Cu catalyst and silanes was developed. This method provides a straightforward and alternative avenue to synthetic important polyfluorinated arenes with readily available and bench-stable alkenes as latent nucleophiles, and therefore avoids conventional reliance on stoichiometric quantities of organometallic reagents. This reaction proceeds under very mild conditions and exhibits good functional group compatibility and high level of regioselectivity. The synthetic potential of this method was further demonstrated by a gram-scale synthesis, and an array of experimental studies were also carried out to elaborate the probable mechanism. 相似文献