Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

被引:15
作者
Dong, Yaxi [1 ]
Breit, Bernhard [1 ]
机构
[1] Albert Ludwigs Univ Freiburg, Inst Organ Chem, D-79104 Freiburg, Germany
关键词
NI-AL; HETEROCYCLES; ACTIVATION; COPPER; HYDROHETEROARYLATION; ALKENYLATION; ALKYLATION; ANNULATION; SWITCH;
D O I
10.1021/acs.orglett.1c02346
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)(2)/Xantphos and catalytic amount of (MeO)(2)MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.
引用
收藏
页码:6765 / 6769
页数:5
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  • [1] Mechanistic Study of a Switch in the Regioselectivity of Hydroheteroarylation of Styrene Catalyzed by Bimetallic Ni-Al through C-H Activation
    Chen, Wen-Ching
    Lai, Ying-Chieh
    Shih, Wei-Chun
    Yu, Ming-Shiuan
    Yap, Glenn P. A.
    Ong, Tiow-Gan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (26) : 8099 - 8105
  • [2] Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile
    Gribble, Michael W., Jr.
    Guo, Sheng
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (15) : 5057 - 5060
  • [3] Divergent Palladium-Catalyzed Cross-Coupling of Nitropyrazoles with Terminal Alkynes
    Ha, Hyeri
    Shin, Changhoon
    Bae, Seri
    Joo, Jung Min
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (20-21) : 2645 - 2650
  • [4] Cu-Catalyzed Regioselective C-H Alkylation of Benzimidazoles with Aromatic Alkenes
    He, Yu-Ting
    Mao, Yang-Jie
    Hao, Hong-Yan
    Xu, Zhen-Yuan
    Lou, Shao-Jie
    Xu, Dan-Qian
    [J]. ORGANIC LETTERS, 2020, 22 (21) : 8250 - 8255
  • [5] Metalation of Pyridines with nBuLi-Li-Aminoalkoxide Mixed Aggregates: The Origin of Chemoselectivity
    Khartabil, Hassan K.
    Gros, Philippe C.
    Fort, Yves
    Ruiz-Lopez, Manuel F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (07) : 2410 - 2416
  • [6] Regioselective C-H alkenylation of imidazoles and its application to the synthesis of unsymmetrically substituted benzimidazoles
    Kim, Hyeongwoo
    Hwang, Ye Ji
    Han, Inhyuk
    Joo, Jung Min
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (50) : 6879 - 6882
  • [7] Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles
    Knippel, James Levi
    Ye, Yuxuan
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2021, 23 (06) : 2153 - 2157
  • [8] Tandem Isomerization and C-H Activation: Regioselective Hydroheteroarylation of Allylarenes
    Lee, Wei-Chih
    Wang, Chun-Han
    Lin, Yung-Huei
    Shih, Wei-Chun
    Ong, Tiow-Gan
    [J]. ORGANIC LETTERS, 2013, 15 (20) : 5358 - 5361
  • [9] N-Heterocyclic Carbene Ligand-Controlled Regioselectivity for Nickel-Catalyzed Hydroarylation of Vinylarenes with Benzothiazoles
    Li, Rui-Peng
    Shen, Zheng-Wang
    Wu, Qin-Jia
    Zhang, Jie
    Sun, Hong-Mei
    [J]. ORGANIC LETTERS, 2019, 21 (13) : 5055 - 5058
  • [10] Enantioselective Aluminum-Free Alkene Hydroarylations through C-H Activation by a Chiral Nickel/JoSPOphos Manifold
    Loup, Joachim
    Mueller, Valentin
    Ghorai, Debasish
    Ackermann, Lutz
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) : 1749 - 1753