A reusable polymer supported copper(I) complex for the C-N bond cross-coupling reaction

被引：23

作者：

Islam, S. M. ^{[1
]}

Mondal, Sanchita ^{[1
]}

Mondal, Paramita ^{[1
]}

Roy, Anupam Singha ^{[1
]}

Tuhina, Kazi

Mobarok, Manir ^{[1
]}

机构：

[1] Univ Kalyani, Dept Chem, Nadia 741235, WB, India

来源：

INORGANIC CHEMISTRY COMMUNICATIONS | 2011年 / 14卷 / 09期

关键词：

PS-LCu(I) catalyst; N-arylation; Amination; Reusable catalyst; CATALYZED AMINATION; ARYLBORONIC ACIDS; HIGHLY EFFICIENT; ARYL HALIDES; ARYLATION; IMIDAZOLES; ALKYLAMINES; AMINES; CU(II); MILD;

D O I：

10.1016/j.inoche.2011.05.019

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The Ullmann coupling of amines with aryl iodide as well as arylboronic acids and N(H)-heterocycles with arylboronic acids has been carried out efficiently using PS-LCu(I) catalyst. The copper complex has been prepared and characterized by using scanning electron microscope (SEM), elemental analysis, atomic absorption spectroscopy (AAS), Thermo gravimetric analysis and spectrometric methods like Fourier transform infrared spectroscopy (FTIR). The effects of various parameters such as temperature, solvent and base on the reaction system were studied. The reusability experiments show that the catalyst can be used five times without much loss in the catalytic activity. (C) 2011 Elsevier B.V. All rights reserved.

引用

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页码：1352 / 1357

页数：6

相关论文

共 23 条

[1] Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].

Antilla, JC ;

Baskin, JM ;

Barder, TE ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587

[2] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[3] Alumina-Supported Cu(II), A Versatile and Recyclable Catalyst for Regioselective Ring Opening of Aziridines and Epoxides and Subsequent Cyclization to Functionalized 1,4-Benzoxazines and 1,4-Benzodioxanes [J].

Bhadra, Sukalyan ;

Adak, Laksmikanta ;

Samanta, Subhas ;

Islam, A. K. M. Maidul ;

Mukherjee, Manabendra ;

Ranu, Brindaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) :8533-8541

[4] Catalytic activities of Cu(II) complexes with nitrogen-chelating bidentate ligands in the coupling of imidazoles with arylboronic acids [J].

Collman, JP ;

Zhong, M ;

Zhang, C ;

Costanzo, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7892-7897

[5] A second-generation catalyst for aryl halide amination: Mixed secondary amines from aryl halides and primary amines catalyzed by (DPPF)PdCl2 [J].

Driver, MS ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7217-7218

[6] Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design [J].

Hartwig, JF .

SYNLETT, 1997, (04) :329-+

[7] Cobalt(II), nickel(II) and copper(II) complexes of 5-(2-carboxyphenylazo)-2-thiohydantoin [J].

Kandil, SS ;

El-Hefnawy, GB ;

Bakr, EA ;

Abou El-Ezz, AZ .

TRANSITION METAL CHEMISTRY, 2003, 28 (02) :168-175

[8] An efficient base-free N-arylation of imidazoles and amines with arylboronic acids using copper-exchanged fluorapatite [J].

Kantam, M. Lakshmi ;

Venkanna, Gopaldasu T. ;

Sridhar, Chidara ;

Sreedhar, Bojja ;

Choudary, Boyapati M. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9522-9524

[9] Mild copper-catalyzed N-arylation of azaheterocycles with aryl halides [J].

Kuil, M ;

Bekedam, EK ;

Visser, GM ;

van den Hoogenband, A ;

Terpstra, JW ;

Kamer, PCJ ;

van Leeuwen, PWNM ;

van Strijdonck, GPF .

TETRAHEDRON LETTERS, 2005, 46 (14) :2405-2409

[10]

Lam PYS, 2000, SYNLETT, P674