Cobalt-catalyzed atroposelective C−H activation/annulation to access N−N axially chiral frameworks

被引:0
|
作者
Tong Li
Linlin Shi
Xinhai Wang
Chen Yang
Dandan Yang
Mao-Ping Song
Jun-Long Niu
机构
[1] Zhengzhou University,College of Chemistry
来源
关键词
D O I
暂无
中图分类号
学科分类号
摘要
The N−N atropisomer, as an important and intriguing chiral system, was widely present in natural products, pharmaceutical lead compounds, and advanced material skeletons. The anisotropic structural characteristics caused by its special axial rotation have always been one of the challenges that chemists strive to overcome. Herein, we report an efficient method for the enantioselective synthesis of N−N axially chiral frameworks via a cobalt-catalyzed atroposelective C-H activation/annulation process. The reaction proceeds under mild conditions by using Co(OAc)2·4H2O as the catalyst with a chiral salicyl-oxazoline (Salox) ligand and O2 as an oxidant, affording a variety of N−N axially chiral products with high yields and enantioselectivities. This protocol provides an efficient approach for the facile construction of N−N atropisomers and further expands the range of of N−N axially chiral derivatives. Additionally, under the conditions of electrocatalysis, the desired N−N axially chiral products were also successfully achieved with good to excellent efficiencies and enantioselectivities.
引用
收藏
相关论文
共 50 条
  • [1] Cobalt-catalyzed atroposelective C-H activation/annulation to access N-N axially chiral frameworks
    Li, Tong
    Shi, Linlin
    Wang, Xinhai
    Yang, Chen
    Yang, Dandan
    Song, Mao-Ping
    Niu, Jun-Long
    [J]. NATURE COMMUNICATIONS, 2023, 14 (01)
  • [2] C-N Axially Chiral Heterobiaryl Skeletons Construction via Cobalt-Catalyzed Atroposelective Annulation
    Li, Tong
    Shi, Linlin
    Zhao, Xiaofang
    Wang, Jianli
    Si, Xiao-Ju
    Yang, Dandan
    Song, Mao-Ping
    Niu, Jun-Long
    [J]. ORGANIC LETTERS, 2023, 25 (28) : 5191 - 5196
  • [3] C-N Axially Chiral Heterobiaryl Isoquinolinone Skeletons Construction via Cobalt-Catalyzed Atroposelective C-H Activation/Annulation
    Wang, Xinhai
    Si, Xiao-Ju
    Sun, Yingjie
    Wei, Zhisen
    Xu, Miao
    Yang, Dandan
    Shi, Linlin
    Song, Mao-Ping
    Niu, Jun-Long
    [J]. ORGANIC LETTERS, 2023, 25 (34) : 6240 - 6245
  • [4] Cobalt-catalyzed enantioselective C-H/N-H annulation of aryl sulfonamides with allenes or alkynes: facile access to C-N axially chiral sultams
    Si, Xiao-Ju
    Zhao, Xiaofang
    Wang, Jianli
    Wang, Xinhai
    Zhang, Yuanshuo
    Yang, Dandan
    Song, Mao-Ping
    Niu, Jun-Long
    [J]. CHEMICAL SCIENCE, 2023, 14 (26) : 7291 - 7303
  • [5] Cobalt-Catalyzed Enantioselective [4+2] Annulation of Benzamides and Alkynes to Synthesize C-N Axially Chiral Isoquinolinones
    Wang, Fen
    Li Xingwei
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 4350 - 4352
  • [6] Carbene-Catalyzed Atroposelective Annulation for Quick Access to Axially Chiral Thiazine Derivatives
    Yang, Xiaoqun
    Li, Tingting
    Chen, Jinli
    Huang, Yixian
    Shen, Tingwei
    Li, Shiguang
    Jin, Zhichao
    Ren, Shi-Chao
    [J]. MOLECULES, 2023, 28 (10):
  • [7] Single-Step Synthesis of Atropisomers with Vicinal C-C and C-N Diaxes by Cobalt-Catalyzed Atroposelective C-H Annulation
    Wang, Bing-Jie
    Xu, Guo-Xiong
    Huang, Zong-Wei
    Wu, Xu
    Hong, Xin
    Yao, Qi-Jun
    Shi, Bing-Feng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (39)
  • [8] Highly Atroposelective Rhodium(II)-Catalyzed N-H Bond Insertion: Access to Axially Chiral N-Arylindolocarbazoles
    Ren, Qiao
    Cao, Tingting
    He, Chunnian
    Yang, Meihua
    Liu, Haitao
    Wang, Lei
    [J]. ACS CATALYSIS, 2021, 11 (10) : 6135 - 6140
  • [9] Cobalt-Catalyzed Oxidase C-H/N-H Alkyne Annulation: Mechanistic Insights and Access to Anticancer Agents
    Mei, Ruhuai
    Wang, Hui
    Warratz, Svenja
    Macgregor, Stuart A.
    Ackermann, Lutz
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (20) : 6759 - 6763
  • [10] Rhodium(III)-Catalyzed Atroposelective Synthesis of C-N Axially Chiral Naphthylamines and Variants via C-H Activation
    Wang, Peiyuan
    Huang, Yaling
    Jing, Jierui
    Wang, Fen
    Li, Xingwei
    [J]. ORGANIC LETTERS, 2022, 24 (13) : 2531 - 2535