4,7-Dimethoxy-1,10-phenanthroline:: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles

被引:268
|
作者
Altman, Ryan A. [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ol0608505
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4,7-Dimethoxy-1,10-phenanthroline (L) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazole with aryl iodides and bromides under mild conditions. A variety of hindered and functionalized imidazoles and aryl halides were transformed in good to excellent yields.
引用
收藏
页码:2779 / 2782
页数:4
相关论文
共 50 条
  • [1] Benzotriazole: an excellent ligand for Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides
    Verma, Akhilesh Kumar
    Singh, Jaspal
    Sankar, V. Kasi
    Chaudhary, Ritu
    Chandra, Ramesh
    [J]. TETRAHEDRON LETTERS, 2007, 48 (24) : 4207 - 4210
  • [2] Pyridine N-Oxides as Ligands in Cu-Catalyzed N-Arylation of Imidazoles in Water
    Liang, Lei
    Li, Zhengkai
    Zhou, Xiangge
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3294 - 3297
  • [3] Copper-Catalyzed Coupling Reactions of Aryl Halides and Phenols by 4,4′-Dimethoxy-2,2′-bipyridine and 4,7-Dimethoxy-1,10-phenanthroline
    Zhao, Yingying
    Wang, Xiangyong
    Kodama, Koichi
    Hirose, Takuji
    [J]. CHEMISTRYSELECT, 2018, 3 (44): : 12620 - 12624
  • [4] Simple synthesized Mannich bases as ligands in Cu-catalyzed N-arylation of imidazoles in water
    Zhu, Yefeng
    Shi, Yixing
    Wei, Yunyang
    [J]. MONATSHEFTE FUR CHEMIE, 2010, 141 (09): : 1009 - 1013
  • [5] Simple synthesized Mannich bases as ligands in Cu-catalyzed N-arylation of imidazoles in water
    Yefeng Zhu
    Yixing Shi
    Yunyang Wei
    [J]. Monatshefte für Chemie - Chemical Monthly, 2010, 141 : 1009 - 1013
  • [6] 3-(Diphenylphosphino)propanoic acid: An efficient ligand for the Cu-catalyzed N-arylation of imidazoles and 1H-pyrazole with aryl halides
    Ya-Shuai Liu
    Yan Liu
    Xiao-Wei Ma
    Ping Liu
    Jian-Wei Xie
    Bin Dai
    [J]. Chinese Chemical Letters, 2014, 25 (05) : 775 - 778
  • [7] 3-(Diphenylphosphino)propanoic acid: An efficient ligand for the Cu-catalyzed N-arylation, of imidazoles and 1H-pyrazole with aryl halides
    Liu, Ya-Shuai
    Liu, Yan
    Ma, Xiao-Wei
    Liu, Ping
    Xie, Jian-Wei
    Dai, Bin
    [J]. CHINESE CHEMICAL LETTERS, 2014, 25 (05) : 775 - 778
  • [8] DNA binding of iron(II) mixed-ligand complexes containing 1,10-phenanthroline and 4,7-diphenyl-1,10-phenanthroline
    Mudasir
    Yoshioka, N
    Inoue, H
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 1999, 77 (3-4) : 239 - 247
  • [9] Iron(II) and nickel(II) mixed-ligand complexes containing 1,10-phenanthroline and 4,7-diphenyl-1,10-phenanthroline
    Mudasir
    Yoshioka N.
    Inoue H.
    [J]. Transition Metal Chemistry, 1999, 24 (2) : 210 - 217
  • [10] NEW, SIMPLE, AND EFFECTIVE THIOSEMICARBAZIDE LIGAND FOR COPPER(II)-CATALYZED N-ARYLATION OF IMIDAZOLES
    Shan, Yuefeng
    Wang, Ying
    Jia, Xiaolei
    Cai, Wenwen
    Xiang, Jiannan
    [J]. SYNTHETIC COMMUNICATIONS, 2012, 42 (08) : 1192 - 1199