Copper-Catalyzed C-N Bond Formation with N-Heterocycles and Aryl Halides

被引:26
作者
Boswell, Mikki G. [1 ]
Yeung, Fanny G. [1 ]
Wolf, Christian [1 ]
机构
[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA
基金
美国国家科学基金会;
关键词
copper; cross-coupling; N-heterocycles; aryl halides; microwave; CROSS-COUPLING REACTIONS; NITROGEN-CONTAINING HETEROCYCLES; LONG-LIVED CATALYSTS; ROOM-TEMPERATURE; AMINO-ACID; PALLADIUM PRECATALYSTS; EFFICIENT CATALYST; ARYLBORONIC ACID; HIGHLY EFFICIENT; AQUEOUS AMMONIA;
D O I
10.1055/s-0031-1290827
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The microwave-assisted, cuprous oxide catalyzed coupling of aryl bromides and iodides with imidazole, benzimidazole, pyrazole, or triazole was found to give a wide range of N-aryl heteroaromatic products in good to high yields. Aryl dibromides undergo selective monosubstitution even in the presence of large excess of N-heterocyclic nucleophiles which leaves the second aryl bromide functionality intact for further derivatization.
引用
收藏
页码:1240 / 1244
页数:5
相关论文
共 50 条
  • [41] Copper-catalyzed C-N bond cross-coupling of aryl halides and amines in water in the presence of ligand derived from oxalyl dihydrazide: scope and limitation
    Kurandina, D. V.
    Eliseenkov, E. V.
    Khaibulova, T. S.
    Petrov, A. A.
    Boyarskiy, V. P.
    TETRAHEDRON, 2015, 71 (41) : 7931 - 7937
  • [42] 3-Acetylcoumarin as a Practical Ligand for Copper-Catalyzed C-N Coupling Reactions at Room Temperature
    Tao, Chuan-Zhou
    Liu, Wei-Wei
    Sun, Ji-You
    Cao, Zhi-Ling
    Li, Hui
    Zhang, Ying-Fen
    SYNTHESIS-STUTTGART, 2010, (08): : 1280 - 1284
  • [43] Assembly of N-Containing Heterocycles via Pd- and Cu-Catalyzed C-N Bond Formation Reactions
    Jiang, Yongwen
    Ma, Dawei
    AMINATION AND FORMATION OF SP2 C-N BONDS, 2013, 46 : 87 - 118
  • [44] Copper-Catalyzed C-N Bond Exchange of N-Heterocyclic Substituents around Pyridine and Pyrimidine Cores
    Tao, Sheng
    Ji, Enhui
    Shi, Lei
    Liu, Ning
    Xu, Liang
    Dai, Bin
    SYNTHESIS-STUTTGART, 2017, 49 (23): : 5120 - 5130
  • [45] C-N Bond Formation at Discrete CuIII-Aryl Complexes
    Reese, Maxwell S.
    Bonanno, Mitchell G.
    Bower, Jamey K.
    Moore, Curtis E.
    Zhang, Shiyu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (49) : 26810 - 26816
  • [46] Copper(II)-Catalyzed C-N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol
    Du, Fangyu
    Zhou, Qifan
    Fu, Yang
    Chen, Yuanguang
    Wu, Ying
    Chen, Guoliang
    SYNLETT, 2019, 30 (19) : 2161 - 2168
  • [47] Copper-catalyzed C-N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride
    Phillips, Dean P.
    Zhu, Xue-Feng
    Lau, Thomas L.
    He, Xiaohui
    Yang, Kunyong
    Liu, Hong
    TETRAHEDRON LETTERS, 2009, 50 (52) : 7293 - 7296
  • [48] An Efficient Copper-Catalyzed Etherification of Aryl Halides
    Huang, Jinkun
    Chen, Ying
    Chan, Johann
    Ronk, Mike L.
    Larsen, Robert D.
    Faul, Margaret M.
    SYNLETT, 2011, (10) : 1419 - 1422
  • [49] Copper-Catalyzed Regioselective Synthesis of N-Aryl Amides from Aldoximes and Aryl Halides
    Panda, Niranjan
    Mothkuri, Raghavender
    Nayak, Dinesh Kumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (08) : 1602 - 1605
  • [50] Copper-Catalyzed Oxidative C-H Amination: Synthesis of Imidazo[1,2-a]-N-Heterocycles from N-Heteroaryl Enaminones
    Reddy, K. Ranjith
    Reddy, A. Siva
    Shankar, Ravi
    Kant, Rajni
    Das, Parthasarathi
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (06) : 573 - 583