Nickel-Catalyzed Regioselective Hydroarylation of Internal Enamides

被引:19
|
作者
Wang, Chenchen [1 ,2 ]
Xi, Yang [1 ,2 ]
Huang, Wenyi [1 ,2 ]
Qu, Jingping [1 ,2 ]
Chen, Yifeng [1 ,2 ]
机构
[1] East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Feringa Nobel Prize Scientist Joint Res Ctr, Key Lab Adv Mat,Sch Chem & Mol Engn, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Feringa Nobel Prize Scientist Joint Res Ctr, Joint Int Res Lab Precis Chem & Mol Engn,Sch Chem, Shanghai 200237, Peoples R China
基金
中国国家自然科学基金;
关键词
DIRECT ARYLATION; CYCLIC ENAMIDES; ALKENES; FUNCTIONALIZATION; HYDROALKYNYLATION; HYDROAMINATION; DERIVATIVES; CYCLIZATION; MECHANISM; IRIDIUM;
D O I
10.1021/acs.orglett.0c03542
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we disclose a nickel-catalyzed three-component reaction of internal enamide, diethoxymethylsilane, and aryl iodide to provide expedient access to benzylic amide derivatives. The protocol features a broad substrate scope with a moderate to excellent isolated yield under the mild condition. The high regioselectivity of Ni-catalyzed enamide hydroarylation can be attributed to the directing effect by the prefunctionalized nitrogen-containing group on the alkenes.
引用
收藏
页码:9319 / 9324
页数:6
相关论文
共 50 条
  • [31] Ligand-modulated nickel-catalyzed regioselective silylalkylation of alkenes
    Chao Ding
    Yaoyu Ren
    Yue Yu
    Guoyin Yin
    Nature Communications, 14
  • [32] Nickel-Catalyzed Chemo- and Regioselective Arylcyanation of β,γ-Unsaturated Amides
    Hu, Jinghui
    Du, Qiang
    Zhao, Yao
    Zhang, Fei
    Chen, Rizhi
    Zhou, Jianrong Steve
    Wu, Xiaojin
    ORGANIC LETTERS, 2022, 24 (24) : 4328 - 4332
  • [33] Macrocyclizations of Ynals: Application of regioselective nickel-catalyzed reductive couplings
    Knauff, Allison R.
    Montgomery, John
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [34] Regioselective synthesis of indenols via nickel-catalyzed carbocyclization reaction
    Rayabarapu, DK
    Yang, CH
    Cheng, CH
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17): : 6726 - 6731
  • [35] ON THE MECHANISM OF THE NICKEL-CATALYZED REGIOSELECTIVE CYCLO-DIMERIZATION OF ISOPRENE
    VANLEEUWEN, PWNM
    ROOBEEK, CF
    TETRAHEDRON, 1981, 37 (10) : 1973 - 1983
  • [36] Ligand-modulated nickel-catalyzed regioselective silylalkylation of alkenes
    Ding, Chao
    Ren, Yaoyu
    Yu, Yue
    Yin, Guoyin
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [37] Access to branched allylsilanes by nickel-catalyzed regioselective hydrosilylation of allenes
    Zeng, Jia-Hao
    Chen, Jun-Jia
    Chen, Li
    Zhan, Zhuang-Ping
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (09) : 1132 - 1136
  • [38] Asymmetric Hydroarylation of Enones via Nickel-Catalyzed 5-Endo-Trig Cyclization
    Qin, Xurong
    Lee, Marcus Wen Yao
    Zhou, Jianrong Steve
    ORGANIC LETTERS, 2019, 21 (15) : 5990 - 5994
  • [39] Nickel-Catalyzed Regio- and Enantioselective Hydroarylation of 1,3-Dienes with Indoles
    Cheng, Lei
    Li, Ming-Ming
    Li, Mao-Lin
    Xiao, Li-Jun
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CCS CHEMISTRY, 2022, 4 (08): : 2612 - 2619
  • [40] Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids
    Li, Zi-Qi
    Fu, Yue
    Deng, Ruohan
    Tran, Van T.
    Gao, Yang
    Liu, Peng
    Engle, Keary M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (51) : 23306 - 23312