Cu2O/Nano-CuFe2O4: An Efficient and Magnetically Recoverable Catalyst for the Ligand-free N-Arylation of Amines and Nitrogen Heterocycles with Aryl Halides

被引：12

作者：

Elhampour, Ali ^{[1
]}

Nemati, Firouzeh ^{[1
]}

Kaveh, Mandieh ^{[1
]}

机构：

[1] Semnan Univ, Dept Chem, Semnan 3513119111, Iran

来源：

CHEMISTRY LETTERS | 2016年 / 45卷 / 02期

关键词：

SULFONIC-ACID GROUPS; AROMATIC-ALDEHYDES; SEPARABLE CATALYST; C-N; COPPER; WATER; DERIVATIVES; IMIDAZOLES;

D O I：

10.1246/cl.151097

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient strategy has been developed for the N-arylation of azoles and aliphatic amines with aryl halide using a Cu2O/nano-CuFe2O4 magnetic composite as the catalyst and KOH as the base. The methodology is found to be applicable to a variety of nitrogen-containing heterocycles, such as imidazole, indole, and pyrrole, as well as aliphatic amines in high yields with practical simplicity under cost-effective "ligand-free" conditions. The magnetic property of the catalyst allowed its fast separation from the reaction medium by an external magnet. Additionally, the inexpensive catalyst could be recycled for five consecutive runs with small drops in catalytic activity.

引用

页码：223 / 225

页数：3

共 30 条

[1] A facile one-step approach for the synthesis of uniform spherical Cu/Cu2O nano- and microparticles with high catalytic activity in the Buchwald-Hartwig amination reaction
Bhosale, Manohar A.
Bhanage, Bhalchandra M.
[J]. RSC ADVANCES, 2014, 4 (29): : 15122 - 15130
[2] An efficient and recyclable chitosan supported copper(II) heterogeneous catalyst for C-N cross coupling between aryl halides and aliphatic diamines
Bodhak, Chandan
Kundu, Ashis
Pramanik, Animesh
[J]. TETRAHEDRON LETTERS, 2015, 56 (02) : 419 - 424
[3] Magnetic nanoparticle-supported proline as a recyclable and recoverable ligand for the CuI catalyzed arylation of nitrogen nucleophiles
Chouhan, Gagan
Wang, Dashan
Alper, Howard
[J]. CHEMICAL COMMUNICATIONS, 2007, (45) : 4809 - 4811
[4] Selective copper catalysed aromatic N-arylation in water
Engel-Andreasen, Jens
Shimpukade, Bharat
Ulven, Trond
[J]. GREEN CHEMISTRY, 2013, 15 (02) : 336 - 340
[5] Copper(I) 3-methylsalicylate, an efficient catalyst for N-arylation of heterocycles under moderate reaction conditions
Farahat, Abdelbasset A.
Boykin, David W.
[J]. TETRAHEDRON LETTERS, 2014, 55 (19) : 3049 - 3051
[6] Silica-decorated magnetic nanocomposites for catalytic applications
Gawande, Manoj B.
Monga, Yukti
Zboril, Radek
Sharma, R. K.
[J]. COORDINATION CHEMISTRY REVIEWS, 2015, 288 : 118 - 143
[7] An efficient, reusable copper-oxide/carbon-nanotube catalyst for N-arylation of imidazole
Gopiraman, Mayakrishnan
Babu, Sundaram Ganesh
Khatri, Zeeshan
Kai, Wei
Kim, Yoong Ahm
Endo, Morinobu
Karvembu, Ramasamy
Kim, Ick Soo
[J]. CARBON, 2013, 62 : 135 - 148
[8] A Highly Versatile Catalytic System for N-Arylation of Amines with Aryl Chlorides in Water
Huang, Manna
Lin, Xiaoqin
Zhu, Xinhai
Peng, Weili
Xie, Jianwei
Wan, Yiqian
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (24) : 4523 - 4527
[9] Ninhydrin: an efficient ligand for the Cu-catalyzed N-arylation of nitro gen-containing heterocycles with aryl halides
Huang, Yi-Zheng
Gao, Jin
Ma, Hong
Miao, Hong
Xu, Jie
[J]. TETRAHEDRON LETTERS, 2008, 49 (06) : 948 - 951
[10] Fe3O4 nanoparticle-supported Cu(II)-β-cyclodextrin complex as a magnetically recoverable and reusable catalyst for the synthesis of symmetrical biaryls and 1,2,3-triazoles from aryl boronic acids
Kaboudin, Babak
Mostafalu, Ramin
Yokomatsu, Tsutomu
[J]. GREEN CHEMISTRY, 2013, 15 (08) : 2266 - 2274

← 1 2 3 →