N-Arylation of nitrogen heterocycles with aryl halides and arylboronic acids catalyzed by cellulose supported copper(0)

被引:91
作者
Reddy, K. Rajender [1 ]
Kumar, Nadakuditi S. [1 ]
Sreedhar, B. [1 ]
Kantam, M. Lakshmi [1 ]
机构
[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India
关键词
copper catalyst; cellulose support; C-N coupling; imidazole; aryl halides; arylboronic acids;
D O I
10.1016/j.molcata.2006.02.053
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Cellulose supported copper(0) catalyst was prepared and employed for the N-arylation of nitrogen heterocycles with a variety of aryl halides and arylboronic acids to afford the corresponding coupled products in good to excellent yields without using external ligands or additives as promoters. The catalyst was recovered by simple filtration and reused for several cycles. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:136 / 141
页数:6
相关论文
共 50 条
[11]   L-(-)-Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles [J].
Zhou, Qifan ;
Du, Fangyu ;
Chen, Yuanguang ;
Fu, Yang ;
Sun, Wenjiao ;
Wu, Ying ;
Chen, Guoliang .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) :8160-8167
[12]   Rh(III)-Catalyzed N-Arylation of Alkyl Dioxazolones with Arylboronic Acids for the Synthesis of N-Aryl Amides [J].
Song, Jia-Lin ;
Chen, Shao-Yong ;
Xiao, Lin ;
Xie, Xiao-Ling ;
Zheng, Yi-Chuan ;
Zhang, Shang-Shi ;
Shu, Bing .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (34)
[13]   Commercial drug norfloxacin as a novel ligand for the copper-catalyzed N-arylation of imidazole with aryl halides [J].
Wu, Fengtian ;
Nan, Chenlong ;
Ma, Minyang ;
Li, Huiqin ;
Xie, Jianwei .
APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (11)
[14]   N-arylation of heterocycles catalyzed by activated-copper in pure water [J].
Yang, Qichao ;
Wang, Yufang ;
Lin, Dong ;
Zhang, Mingjie .
TETRAHEDRON LETTERS, 2013, 54 (15) :1994-1997
[15]   Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids [J].
Tang, Jing-Jing ;
Yu, Xiaoqiang ;
Yamamoto, Yoshinori ;
Bao, Ming .
ACS CATALYSIS, 2021, 11 (22) :13955-13961
[16]   Nickel-catalyzed N-arylation of amines with arylboronic acids under open air [J].
Ando, Shin ;
Hirota, Yurina ;
Matsunaga, Hirofumi ;
Ishizuka, Tadao .
TETRAHEDRON LETTERS, 2019, 60 (18) :1277-1280
[17]   A Practical Copper Catalyzed N-Arylation of Amines Using Aryl Triazenes as Aryl Source [J].
Chand, Shiv ;
Kumar, Saurabh ;
Singh, Rahul ;
Singh, Krishna Nand .
CHEMISTRYSELECT, 2019, 4 (02) :718-721
[18]   N-Arylation of nitrogen heterocycles with 2,4-difluoroiodobenzene [J].
Jitchati, Rukkiat ;
Batsanov, Andrei S. ;
Bryce, Martin R. .
TETRAHEDRON, 2009, 65 (04) :855-861
[19]   Ligand complex of copper (II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: an efficient and magnetically separable catalyst for N-arylation of nitrogen-containing heterocycles with aryl halides [J].
Zahmatkesh, Saeed ;
Esmaeilpour, Mohsen ;
Poli, Azade Mollaiy .
INORGANIC AND NANO-METAL CHEMISTRY, 2019, 49 (10) :323-334
[20]   Highly Functional Group Tolerance in Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles under Mild Conditions [J].
Zhu, Liangbo ;
Li, Gaocan ;
Luo, Liang ;
Guo, Peng ;
Lan, Jingbo ;
You, Jingsong .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05) :2200-2202