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
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共 52 条
  • [1] Copper-Catalyzed Dehydrogenative Coupling of Arenes with Alcohols
    Bhadra, Sukalyan
    Matheis, Christian
    Katayev, Dmitry
    Goossen, Lukas J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9279 - 9283
  • [2] Synthesis of Aryl Ethers from Benzoates through Carboxylate-Directed C-H-Activating Alkoxylation with Concomitant Protodecarboxylation
    Bhadra, Sukalyan
    Dzik, Wojciech I.
    Goossen, Lukas J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (10) : 2959 - 2962
  • [3] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    Brasche, Gordon
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934
  • [4] Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C-H Bond Arylation
    Chen, Bo
    Hou, Xue-Long
    Li, Yu-Xue
    Wu, Yun-Dong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) : 7668 - 7671
  • [5] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
    Chen, Xiao
    Hao, Xue-Shi
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791
  • [6] Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions
    Cho, Seung Hwan
    Yoon, Jungho
    Chang, Sukbok
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) : 5996 - 6005
  • [7] Catalytic C-H amination: the stereoselectivity issue
    Collet, Florence
    Lescot, Camille
    Dauban, Philippe
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) : 1926 - 1936
  • [8] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds
    Daugulis, Olafs
    Do, Hien-Quang
    Shabashov, Dmitry
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) : 1074 - 1086
  • [9] Cu-Catalyzed Mild C(sp2)-H Functionalization Assisted by Carboxylic Acids en Route to Hydroxylated Arenes
    Gallardo-Donaire, Joan
    Martin, Ruben
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) : 9350 - 9353
  • [10] Copper-Catalyzed sp3 C-H Amination
    Gephart, Raymond T., III
    Warren, Timothy H.
    [J]. ORGANOMETALLICS, 2012, 31 (22) : 7728 - 7752