Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones

被引:11
|
作者
Nozawa-Kumada, Kanako [1 ]
Matsuzawa, Yuta [1 ]
Ono, Kanako [1 ]
Shigeno, Masanori [1 ]
Kondo, Yoshinori [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, 6-3 Aoba, Sendai, Miyagi 9808578, Japan
基金
日本学术振兴会;
关键词
C-H ACTIVATION; 3+2 ANNULATION; OXIDATION; AMINATION; DERIVATIVES; MOLECULES; KETIMINES; ALKYNES;
D O I
10.1039/d1cc02870g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A copper-catalyzed aerobic 3-hydroxyisoindolinone synthesis was developed via the benzylic double C(sp(3))-H functionalization of 2-alkylbenzamides. In this reaction, molecular oxygen was used as both an oxidant for C(sp(3))-H functionalization and an oxygen source. Our method can be extended to diverse benzylic C(sp(3))-H bonds and shows excellent functional group tolerance.
引用
收藏
页码:8604 / 8607
页数:4
相关论文
共 50 条
  • [31] Enantioselective functionalization of unactivated C(sp3)-H bonds through copper-catalyzed diyne cyclization by kinetic resolution
    Chen, Yang-Bo
    Liu, Li-Gao
    Wang, Zhe-Qi
    Chang, Rong
    Lu, Xin
    Zhou, Bo
    Ye, Long-Wu
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [32] Copper catalyzed benzylic sp3 C-H alkenylation
    Chen, Ting-An
    Staples, Richard J.
    Warren, Timothy H.
    CHEMICAL SCIENCE, 2024, 15 (42) : 17685 - 17690
  • [33] Copper-Catalyzed Tandem Aerobic Oxidative Cyclization for the Synthesis of Polysubstituted Quinolines via C(sp3)/C(sp2)-H Bond Functionalization
    Pang, Xiaobo
    Wu, Mingzhong
    Ni, Jixiang
    Zhang, Fuming
    Lan, Jingfeng
    Chen, Baohua
    Yan, Rulong
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19): : 10110 - 10120
  • [34] Organopotassium-Catalyzed Silylation of Benzylic C(sp3)-H Bonds
    Neil, Baptiste
    Saadi, Lamine
    Fensterbank, Louis
    Chauvier, Clement
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (31)
  • [35] Copper-Catalyzed sp3 C-H Amination
    Gephart, Raymond T., III
    Warren, Timothy H.
    ORGANOMETALLICS, 2012, 31 (22) : 7728 - 7752
  • [36] Copper-Catalyzed γ-C(sp3)-H Lactamization and Iminolactonization
    Sheng, Tao
    Zhuang, Zhe
    Zhao, Zhihan
    Hoque, Md Emdadul
    Yu, Jin-Quan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (04)
  • [37] Synthesis of functionalized benzoxazines by copper-catalyzed C(sp3)-H bond functionalization of acetonitrile with olefinic amides
    Chu, Xue-Qiang
    Xu, Xiao-Ping
    Meng, Hua
    Ji, Shun-Jun
    RSC ADVANCES, 2015, 5 (83): : 67829 - 67832
  • [38] Selective functionalization of benzylic C(sp3)-H bonds to synthesize complex molecules
    Zhang, Yu
    Zhang, Tong
    Das, Shoubhik
    CHEM, 2022, 8 (12): : 3175 - 3201
  • [39] Copper-Catalyzed Aerobic C(sp3)-H Oxidation of β-(Alkoxy)imino Carbonyl Compounds
    Ueda, Masafumi
    Ichimonji, Ayano
    Nakayama, Miku
    Ito, Sachiko
    Takeda, Norihiko
    Yasui, Motohiro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2023, 71 (02) : 83 - 92
  • [40] Unexpected Copper-Catalyzed Aerobic Oxidative Cleavage of C(sp3)-C(sp3) Bond of Glycol Ethers
    Liu, Zhong-Quan
    Zhao, Lixing
    Shang, Xiaojie
    Cui, Zili
    ORGANIC LETTERS, 2012, 14 (12) : 3218 - 3221