Pd(II)-Catalyzed para-Selective C-H Arylation of Monosubstituted Arenes

被引:277
|
作者
Wang, Xisheng [1 ]
Leow, Dasheng [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
基金
美国国家卫生研究院;
关键词
CATALYZED ORTHO-ARYLATION; BOND FORMATION; REDUCTIVE ELIMINATION; OXIDATIVE ARYLATION; FUNCTIONALIZATION; ACTIVATION; ELECTRON; BENZENE; COMPLEXES; BIPHENYL;
D O I
10.1021/ja206572w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd-catalyzed highly para-selective C-H arylation of monosubstituted arenes (including toluene) is developed for the first time using an F+ reagent as a bystanding oxidant. This finding provides a new retrosynthetic disconnection for para-substituted biaryl synthesis via C-H/C-H cross-coupling.
引用
收藏
页码:13864 / 13867
页数:4
相关论文
共 50 条
  • [1] Ligand-Controlled Para-Selective C-H Arylation of Monosubstituted Arenes
    Xu, Hui
    Shang, Ming
    Dai, Hui-Xiong
    Yu, Jin-Quan
    ORGANIC LETTERS, 2015, 17 (15) : 3830 - 3833
  • [2] Dinuclear Gold-Catalyzed para-Selective C-H Arylation of Undirected Arenes by Noncovalent Interactions
    Liu, Duan-Yang
    Han, Jie
    Liu, Kai
    Cheng, Yaohang
    Tan, Hairen
    Yang, Xiaoliang
    Li, Weipeng
    Xie, Jin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (44)
  • [3] para-Selective C-H Amidation of Simple Arenes with Nitriles
    Xiang, Shi-Kai
    Li, Jin-Mei
    Huang, He
    Feng, Chun
    Ni, Hai-Liang
    Chen, Xiao-Zhen
    Wang, Bi-Qin
    Zhao, Ke-Qing
    Hu, Ping
    Redshaw, Carl
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) : 3435 - 3440
  • [4] Pd-Catalyzed para-selective C-H difluoromethylation of aromatic carbonyls
    Mao, Yang-Jie
    Wang, Bing-Xin
    Wu, Qiu-Zi
    Zhou, Kun
    Lou, Shao-Jie
    Xu, Dan-Qian
    CHEMICAL COMMUNICATIONS, 2019, 55 (14) : 2019 - 2022
  • [5] Theoretical Studies on Pd(II)-Catalyzed meta-Selective C-H Bond Arylation of Arenes
    Deng, Chao
    Zhang, Jing-Xuan
    Lin, Zhenyang
    ACS CATALYSIS, 2018, 8 (03): : 2498 - 2507
  • [6] Copper-Catalyzed para-Selective C-H Amination of Electron-Rich Arenes
    Berzina, Beatrise
    Sokolovs, Igors
    Suna, Edgars
    ACS CATALYSIS, 2015, 5 (11): : 7008 - 7014
  • [7] Ligand Promoted Pd-Catalyzed High para-Selective C-H Olefination
    Shen, Shuo-Jie
    Li, Yao-Dong
    Ge, Ye
    Yang, Xu
    Li, Lin-Hu
    Xu, Hua-Jin
    Hu, Yi
    ORGANIC LETTERS, 2023, 25 (51) : 9092 - 9096
  • [8] Para-Selective Cu-Catalyzed C-H Aryloxylation of Electron-Rich Arenes and Heteroarenes
    Sokolovs, Igors
    Suna, Edgars
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (02): : 371 - 379
  • [9] Trialkoxysilane-Induced Iridium-Catalyzed para-Selective C-H Bond Borylation of Arenes
    Ju, Guodong
    Huang, Zhibin
    Zhao, Yingsheng
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [10] Para-Selective C-H Thioetherification
    Hsu, Wei-Chieh
    Li, Chao-En
    Lee, Chin-Fa
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (11) : 1667 - 1673