Hydrogen-Atom Transfer Catalysis for C-H Alkylation of Benzylic Fluorides

被引：6
作者：
Ohmatsu, Kohsuke [1 ,2 ]
Suzuki, Ryuhei [1 ,2 ]
Fujita, Hiroki [1 ,2 ]
Ooi, Takashi [1 ,2 ]
机构：
[1] Nagoya Univ, Grad Sch Engn, Inst Transformat BioMol WPIITbM, Nagoya, Aichi 4648601, Japan
[2] Nagoya Univ, Grad Sch Engn, Dept Mol & Macromol Chem, Nagoya, Aichi 4648601, Japan
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 17期
关键词：
LATE-STAGE FUNCTIONALIZATION; ACTIVATED ALKENES; DECATUNGSTATE ANION; BOND; PHOTOCATALYSIS; SUBSTITUTION;
D O I：
10.1021/acs.orglett.2c00817
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A photoinduced catalytic C(sp3)-H alkylation of benzylicfluorides is developed. The use of zwitterionic 1,2,3-triazolium amidate as ahydrogen-atom transfer catalyst is uniquely effective for promoting thistransformation. The combination of C-H alkylation with subsequentdisplacement of the C-F bond enables 1,1-difunctionalization of benzylicfluorides, providing rapid access to an array of functionalized molecularentities
引用
收藏
页码：3134 / 3137
页数：4
相关论文
共 44 条
  • [1] Multiple Catalytic C-H Bond Functionalization for Natural Product Synthesis
    Baudoin, Olivier
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (41) : 17798 - 17809
  • [2] Site-Selective Late-Stage C-H Functionalization via Thianthrenium Salts
    Berger, Florian
    Ritter, Tobias
    [J]. SYNLETT, 2022, 33 (04) : 339 - 345
  • [3] THE PREPARATION AND PROPERTIES OF SOME SUBSTITUTED BENZYL FLUORIDES
    BERNSTEIN, J
    ROTH, JS
    MILLER, WT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (07) : 2310 - 2314
  • [4] Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides
    Blessley, George
    Holden, Patrick
    Walker, Matthew
    Brown, John M.
    Gouverneur, Veronique
    [J]. ORGANIC LETTERS, 2012, 14 (11) : 2754 - 2757
  • [5] Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds
    Cannalire, Rolando
    Pelliccia, Sveva
    Sancineto, Luca
    Novellino, Ettore
    Tron, Gian Cesare
    Giustiniano, Mariateresa
    [J]. CHEMICAL SOCIETY REVIEWS, 2021, 50 (02) : 766 - 897
  • [6] Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration
    Capaldo, Luca
    Ravelli, Davide
    Fagnoni, Maurizio
    [J]. CHEMICAL REVIEWS, 2022, 122 (02) : 1875 - 1924
  • [7] Photocatalytic hydrogen atom transfer: the philosopher's stone for late-stage functionalization?
    Capaldo, Luca
    Quadri, Lorenzo Lafayette
    Ravelli, Davide
    [J]. GREEN CHEMISTRY, 2020, 22 (11) : 3376 - 3396
  • [8] Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis
    Capaldo, Luca
    Ravelli, Davide
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) : 2056 - 2071
  • [9] The medicinal chemist's toolbox for late stage functionalization of drug-like molecules
    Cernak, Tim
    Dykstra, Kevin D.
    Tyagarajan, Sriram
    Vachal, Petr
    Krska, Shane W.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) : 546 - 576
  • [10] Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of C-F Bonds as Enabled by Hydrogen Bonding
    Champagne, Pier Alexandre
    Benhassine, Yasmine
    Desroches, Justine
    Paquin, Jean-Francois
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) : 13835 - 13839
12345