Electrochemical Ruthenium-Catalysed Directed C-H Functionalization of Arenes with Boron Reagents

被引:0
|
作者
Kenyon, Jacob [1 ]
Larrosa, Igor [1 ]
机构
[1] Univ Manchester, Dept Chem, Oxford Rd, Manchester M13 9PL, England
基金
英国工程与自然科学研究理事会; 欧洲研究理事会;
关键词
C-H activation; electrochemistry; homogeneous catalysis; ARYLATION; ALKYL; ACIDS; ARYL; NICKEL; BONDS; IRON;
D O I
10.1002/adsc.202301184
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Ortho-directed electrochemical C-H functionalization of aromatics with boron-based coupling partners has been achieved under ruthenium catalysis through an oxidatively induced reductive elimination mechanism. Our method provides a single set of conditions delivering C-H arylation, alkenylation and methylation, yielding ortho-functionalized products with good functional group tolerance, including examples of late-stage functionalization in synthetically useful yields. By harnessing electricity as a 'green' oxidant, this method circumvents the need for stoichiometric quantities of chemical oxidants, enhancing our sustainability metrics. image
引用
收藏
页码:830 / 837
页数:8
相关论文
共 50 条
  • [1] Ruthenium-catalysed dehydrogenative C-H borylation of arenes with pinacolborane
    Murata, Miki
    Ueda, Yosuke
    Hyogo, Mayu
    Kohari, Yoshihito
    Namikoshi, Takeshi
    Watanabe, Shinji
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2016, (07) : 393 - 396
  • [2] Improving the sustainability of the ruthenium-catalysed N-directed C-H arylation of arenes with aryl halides
    Findlay, Michael T.
    Hogg, Ashley S.
    Douglas, James J.
    Larrosa, Igor
    [J]. GREEN CHEMISTRY, 2023, 25 (06) : 2394 - 2400
  • [3] Electrochemical ruthenium-catalysed C-H activation in water through heterogenization of a molecular catalyst
    Buehler, Jan
    Zurflueh, Jonas
    Siol, Sebastian
    Blacque, Olivier
    Severy, Laurent
    Tilley, S. David
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2022, 12 (05) : 1512 - 1519
  • [4] Ruthenium-catalysed σ-activation for remote meta-selective C-H functionalisation
    Leitch, Jamie A.
    Frost, Christopher G.
    [J]. CHEMICAL SOCIETY REVIEWS, 2017, 46 (23) : 7145 - 7153
  • [5] Ruthenium-catalysed C-H/C-N bond activation: facile access to isoindolinones
    Hu, Xiao-Qiang
    Hou, Ye-Xing
    Liu, Zi-Kui
    Gao, Yang
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (05) : 915 - 921
  • [6] Palladium-catalysed norbornene-mediated C-H functionalization of arenes
    Ye, Juntao
    Lautens, Mark
    [J]. NATURE CHEMISTRY, 2015, 7 (11) : 863 - 870
  • [7] Recent advances in ruthenium-catalysed aromatic C-H bond oxygenation, nitrogenation and halogenation
    Singh, Keisham S.
    [J]. CHEMISTRYSELECT, 2024, 9 (07):
  • [8] Transition metal-catalysed directed C-H functionalization with nucleophiles
    Barranco, Sergio
    Zhang, Jiayu
    Lopez-Resano, Sara
    Casnati, Alessandra
    Perez-Temprano, Monica H.
    [J]. NATURE SYNTHESIS, 2022, 1 (11): : 841 - 853
  • [9] INOR 55-Directed C-H functionalization with ruthenium boron analogs of the Shvo hydrogenation catalyst
    Casey, Charles P.
    Clark, Timothy B.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 247 - 247
  • [10] Electrochemical C-H Functionalization of (Hetero)Arenes-Optimized by DoE
    Doerr, Maurice
    Roeckl, Johannes L.
    Rein, Jonas
    Schollmeyer, Dieter
    Waldvogel, Siegfried R.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (45) : 10195 - 10198