Copper-Catalyzed Carboxamide-Directed Ortho Amination of Anilines with Alkylamines at Room Temperature

被引:179
|
作者
Li, Qiong [1 ]
Zhang, Shu-Yu [1 ]
He, Gang [1 ]
Ai, Zhaoyan [1 ]
Nack, William A. [1 ]
Chen, Gong [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
基金
美国国家科学基金会;
关键词
C-H BONDS; UNACTIVATED C(SP(3))-H; C(SP(2))-H BONDS; PALLADIUM; ARYLATION; FUNCTIONALIZATION; ALKOXYLATION; ALKYLATION; COMPLEXES; OXIDATION;
D O I
10.1021/ol500464x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.
引用
收藏
页码:1764 / 1767
页数:4
相关论文
共 50 条
  • [1] Copper-Catalyzed Oxalamide-Directed ortho-C-H Amination of Anilines with Alkylamines
    Wu, Peng
    Huang, Wei
    Cheng, Tai-Jin
    Lin, Hai-Xia
    Xu, Hui
    Dai, Hui-Xiong
    ORGANIC LETTERS, 2020, 22 (13) : 5051 - 5056
  • [2] Copper-catalyzed ortho-C-H amination of protected anilines with secondary amines
    Manu Martinez, Angel
    Rodriguez, Nuria
    Gomez Arrayas, Ramon
    Carretero, Juan C.
    CHEMICAL COMMUNICATIONS, 2014, 50 (21) : 2801 - 2803
  • [3] Room Temperature, Copper-Catalyzed Amination of Bromonaphthyridines with Aqueous Ammonia
    Anderson, Cyrus A.
    Taylor, Phillip G.
    Zeller, Mary A.
    Zimmerman, Steven C.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14): : 4848 - 4851
  • [4] Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature
    Zhu, Haibo
    Shen, Yajing
    Deng, Qinyue
    Tu, Tao
    CHEMICAL COMMUNICATIONS, 2015, 51 (92) : 16573 - 16576
  • [5] Copper-catalyzed ortho-halogenation of protected anilines
    Urones, Beatriz
    Manu Martinez, Angel
    Rodriguez, Nuria
    Gomez Arrayas, Ramon
    Carretero, Juan C.
    CHEMICAL COMMUNICATIONS, 2013, 49 (94) : 11044 - 11046
  • [6] Room-Temperature Practical Copper-Catalyzed Amination of Aryl Iodides
    Deldaele, Christopher
    Evano, Gwilherm
    CHEMCATCHEM, 2016, 8 (07) : 1319 - 1328
  • [7] Copper-catalyzed monoselective C-H amination of ferrocenes with alkylamines
    Jia, Zhen-Sheng
    Yue, Qiang
    Li, Ya
    Xu, Xue-Tao
    Zhang, Kun
    Shi, Bing-Feng
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 2488 - 2495
  • [8] Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines
    Kwong, FY
    Buchwald, SL
    ORGANIC LETTERS, 2003, 5 (06) : 793 - 796
  • [9] Room-temperature copper-catalyzed electrophilic amination of arylcadmium iodides with ketoximes
    Korkmaz, Adem
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2021, 18 (11) : 3119 - 3125
  • [10] Room-temperature copper-catalyzed electrophilic amination of arylcadmium iodides with ketoximes
    Adem Korkmaz
    Journal of the Iranian Chemical Society, 2021, 18 : 3119 - 3125