The electrophilic aromatic substitution approach to C-H silylation and C-H borylation

被引:21
|
作者
Baehr, Susanne [1 ]
Oestreich, Martin [1 ]
机构
[1] Tech Univ Berlin, Inst Chem, Str 17,Juni 115, D-10623 Berlin, Germany
关键词
boron electrophiles; C-H functionalization; cooperative catalysis; electrophilic aromatic substitution; IMEBORON-16; silicon electrophiles; RU-S BONDS; COMPLEXES; ACTIVATION; HYDROSILANES; GENERATION; PYRIDINES; CLEAVAGE; ANION; IONS; BARF;
D O I
10.1515/pac-2017-0902
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several approaches toward electrophilic C-H silylation of electron-rich arenes are discussed, comprising transition-metal-catalyzed processes as well as Lewis-acid-and Bronsted-acid-induced protocols. These methods differ in the catalytic generation of the silicon electrophile but share proton removal in form of dihydrogen. With slight modifications, these methods are often also applicable to the related electrophilic C-H borylation.
引用
收藏
页码:723 / 731
页数:9
相关论文
共 50 条
  • [1] Borylation and Silylation of C-H Bonds: A Platform for Diverse C-H Bond Functionalizations
    Hartwig, John F.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 864 - 873
  • [2] Intramolecular (directed) electrophilic C-H borylation
    Iqbal, S. A.
    Pahl, J.
    Yuan, K.
    Ingleson, M. J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2020, 49 (13) : 4564 - 4591
  • [3] Electrophilic Aromatic Substitution with Silicon Electrophiles: Catalytic Friedel-Crafts C-H Silylation
    Baehr, Susanne
    Oestreich, Martin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) : 52 - 59
  • [4] Aromatic C-H Borylation by Nickel Catalysis
    Zhang, Hua
    Hagihara, Shinya
    Itami, Kenichiro
    [J]. CHEMISTRY LETTERS, 2015, 44 (06) : 779 - 781
  • [5] Zinc catalysed electrophilic C-H borylation of heteroarenes
    Grundy, Matthew E.
    Yuan, Kang
    Nichol, Gary S.
    Ingleson, Michael J.
    [J]. CHEMICAL SCIENCE, 2021, 12 (23) : 8190 - 8198
  • [6] Sterically controlled C-H/C-H homocoupling of arenes via C-H borylation
    Pei, Xiaocong
    Zhou, Guan
    Li, Xuejing
    Xu, Yuchen
    Panicker, Resmi C.
    Srinivasan, Rajavel
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (23) : 5703 - 5707
  • [7] Luminescent organoboron ladder compounds via directed electrophilic aromatic C-H borylation
    Yusuf, Mayyadah
    Liu, Kanglei
    Guo, Fang
    Lalancette, Roger A.
    Jaekle, Frieder
    [J]. DALTON TRANSACTIONS, 2016, 45 (11) : 4580 - 4587
  • [8] A Minisci Approach to C-H Borylation of Azines
    Kim, Ji Hye
    Constantin, Timothee
    Simonetti, Marco
    Llaveria, Josep
    Sheikh, Nadeem S.
    Leonori, Daniele
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (19): : A162 - A165
  • [9] A Minisci Approach to C-H Borylation of Azines
    Kim, Ji Hye
    Constantin, Timothee
    Simonetti, Marco
    Llaveria, Josep
    Sheikh, Nadeem S.
    Leonori, Daniele
    [J]. SYNLETT, 2021, 32 (16) : A162 - A165
  • [10] Quadruple C-H activation coupled to hydrofunctionalization and C-H silylation/borylation enabled by weakly coordinated palladium catalyst
    Tang, Bo-Cheng
    Lin, Wen-Xuan
    Chen, Xiang-Long
    He, Cai
    Ma, Jin-Tian
    Wu, Yan-Dong
    Lan, Yu
    Wu, An-Xin
    [J]. NATURE COMMUNICATIONS, 2020, 11 (01)