An efficient and recyclable chitosan supported copper(II) heterogeneous catalyst for C-N cross coupling between aryl halides and aliphatic diamines

被引:39
作者
Bodhak, Chandan [1 ]
Kundu, Ashis [1 ]
Pramanik, Animesh [1 ]
机构
[1] Univ Calcutta, Dept Chem, Kolkata 700009, India
关键词
Aryl halides; 1,2-and 1,3-diamines/amino alcohols; Chitosan@copper catalyst; Chelation pathway; BOND FORMATION; NATURAL-PRODUCTS; AMINO-ACID; MILD; AMINATION; ARYLATION; IODIDES; ALKYLAMINES; AMIDATION;
D O I
10.1016/j.tetlet.2014.11.120
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A useful and convenient methodology has been developed for synthesis of mono N-arylated aliphatic 1,2- and 1,3-diamines and amino alcohols. A highly efficient and renewable heterogeneous chitosan supported copper(II) catalyst has been employed for the C-N cross coupling between aryl halides and aliphatic diamines/amino alcohols. The main advantages of this reaction are the high yields of the products, reduced reaction time, convenient work up procedure, renewability of the catalyst, and less metal contamination of the products. All these factors make the present C-N cross coupling reaction economical, green, and sustainable. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:419 / 424
页数:6
相关论文
共 41 条
[1]   Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates [J].
Ackermann, Lutz ;
Sandmann, Rene ;
Song, Weifeng .
ORGANIC LETTERS, 2011, 13 (07) :1784-1786
[2]   Copper-Catalyzed Arylation of Oxadiamines and Polyamines [J].
Anokhin, Maxim V. ;
Averin, Alexei D. ;
Beletskaya, Irina P. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (31) :6240-6253
[3]   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
[4]   Copper on chitosan: a recyclable heterogeneous catalyst for azide-alkyne cycloaddition reactions in water [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
GREEN CHEMISTRY, 2013, 15 (07) :1839-1843
[5]   The influence of salinity on acute nickel toxicity to the two euryhaline fish species, Fundulus heteroclitus and Kryptolebias marmoratus [J].
Bielmyer, Gretchen K. ;
DeCarlo, Carri ;
Morris, Cameron ;
Carrigan, Thomas .
ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY, 2013, 32 (06) :1354-1359
[6]   Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].
Buchwald, SL ;
Mauger, C ;
Mignani, G ;
Scholz, U .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39
[7]  
Buckingham J., 1994, DICT NATURAL PRODUCT, V1
[8]  
Cheng JH, 2001, CARDIOVASC DRUG REV, V19, P152
[9]   Copper-catalyzed C-N cross-coupling reactions for the preparation of aryl diamines applying mild conditions [J].
Costa, Marcio V. ;
Viana, Gil M. ;
de Souza, Thais M. ;
Malta, Luiz Fernando B. ;
Aguiar, Lucia C. S. .
TETRAHEDRON LETTERS, 2013, 54 (19) :2332-2335
[10]  
Craig P.N., 1991, COMPREHENSIVE MED CH, P8