Ligand-free copper-catalyzed arylation of imidazole and N,N′-carbonyldiimidazole, and microwave-assisted synthesis of N-Aryl-1H-imidazoles

被引:14
|
作者
Yang, Xiao-Dong [1 ]
Li, Liang [1 ]
Zhang, Hong-Bin [1 ]
机构
[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Yunnan, Peoples R China
关键词
D O I
10.1002/hlca.200890156
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Microwave-assisted arylation of 1H-imidazoles and N,N'-carbonyldiinidazole under ligand-free copper-mediated conditions in tetraethyl orthosilicate is reported. Valuable evidence for understanding of the Cu-catalyzed mechanism of the Ullmann reaction is also presented.
引用
收藏
页码:1435 / 1442
页数:8
相关论文
共 50 条
  • [11] Ligand free copper-catalyzed N-arylation of heteroarylamines
    Wang, Deping
    Kuang, Daizhi
    Zhang, Fuxing
    Liu, Yang
    Ning, Shunhua
    TETRAHEDRON LETTERS, 2014, 55 (51) : 7121 - 7123
  • [12] Ligand-free copper(I) catalyzed N- and O-arylation of aryl halides
    Sperotto, Elena
    de Vries, Johannes G.
    van Klink, Gerard P. M.
    van Koten, Gerard
    TETRAHEDRON LETTERS, 2007, 48 (41) : 7366 - 7370
  • [13] Copper catalyzed N-arylation of sulfonamides with aryl bromides under ligand-free conditions
    Teo, Yong-Chua
    Tan, Yun-Ru
    Saanvi, M. Kyra
    Loh, Chu-Ken
    Tan, Swee-Ngin
    SYNTHETIC COMMUNICATIONS, 2023, 53 (14) : 1143 - 1152
  • [14] Ligand-Free Copper-Catalyzed Arylation of Phosphonamides and Phosphinamides with Aryl Siloxanes
    Zhong, Longjin
    Su, Qiong
    Xiao, Jing
    Peng, Zhihong
    Dong, Wanrong
    Zhang, Yingjun
    An, Delie
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (08) : 1072 - 1079
  • [15] Commercial drug norfloxacin as a novel ligand for the copper-catalyzed N-arylation of imidazole with aryl halides
    Wu, Fengtian
    Nan, Chenlong
    Ma, Minyang
    Li, Huiqin
    Xie, Jianwei
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (11)
  • [16] Efficient ligand-free copper catalyzed N-arylation of sulfonamides
    Yong-Chua, Teo
    Yong, Fui-Fong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [17] Aryl triolborates: Novel reagent for copper-catalyzed N arylation of amines, anilines, and imidazoles
    Yu, Xiao-Qiang
    Yamamoto, Yasunori
    Miyaura, Norio
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1517 - 1522
  • [18] Ligand-Free, Copper-Catalyzed Coupling Reaction of Aryl Aluminum Reagents with N-Aryl Thiosuccinimides
    Zhang, Zhihao
    Jia, Xiaoying
    Pu, Jiaxia
    Han, Lirong
    Hou, Jinsong
    Li, Qinghan
    LETTERS IN ORGANIC CHEMISTRY, 2024, 21 (12) : 1055 - 1063
  • [19] Mild Conditions for Copper-Catalyzed N-Arylation of Imidazoles
    Chen, Huaming
    Wang, Deping
    Wang, Xianyang
    Huang, Wenlong
    Cai, Qian
    Ding, Ke
    SYNTHESIS-STUTTGART, 2010, (09): : 1505 - 1511
  • [20] Ligand-Free Copper-Catalyzed N-Arylation of Pyrazolo[1,5-a]pyrimidin-7-Amines
    Pang, Ting
    Sang, Tian
    He, Jing
    Guo, Ruili
    Xie, Jianwei
    Liu, Ping
    APPLIED ORGANOMETALLIC CHEMISTRY, 2025, 39 (03)