Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis

被引：123
作者：
Noto, Naoki [1 ]
Koike, Takashi [1 ]
Akita, Munetaka [1 ]
机构：
[1] Tokyo Inst Technol, Inst Innovat Res, Lab Chem & Life Sci, Midori Ku, R1-27,4259 Nagatsuta Cho, Yokohama, Kanagawa 2268503, Japan
来源：
CHEMICAL SCIENCE | 2017年 / 8卷 / 09期
关键词：
FLUOROALKYLATION REACTIONS; RADICAL POLYMERIZATION; TRIFLUOROMETHYLATION; DRIVEN; EFFICIENT; OXYDIFLUOROMETHYLATION; DIFUNCTIONALIZATION;
D O I：
10.1039/c7sc01703k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Regioselective amino-difluoromethylation of aromatic alkenes via C(sp(3))-CF2H and C(sp(3))-N bond formation with the C=C moiety has been achieved in a single operation by visible-light photoredox catalysis. The combination of a shelf-stable and easy-to-handle sulfonium salt, S-difluoromethyl-S-di(p-xylyl) sulfonium tetrafluoroborate, and perylene catalysis is the key to the successful transformation. Furthermore, this noble metal-free protocol allows for the photocatalytic trifluoromethylation of alkenes.
引用
收藏
页码：6375 / 6379
页数：5
相关论文
共 49 条
  • [1] Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes
    Alonso, Concepcion
    Martinez de Marigorta, Eduardo
    Rubiales, Gloria
    Palacios, Francisco
    [J]. CHEMICAL REVIEWS, 2015, 115 (04) : 1847 - 1935
  • [2] Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols
    Arai, Yusuke
    Tomita, Ren
    Ando, Gaku
    Koike, Takashi
    Akita, Munetaka
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (04) : 1262 - 1265
  • [3] Photocatalytic fluoroalkylation reactions of organic compounds
    Barata-Vallejo, Sebastian
    Bonesi, Sergio M.
    Postigo, Al
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11153 - 11183
  • [4] Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp2) and C(sp) Centers
    Belhomme, Marie-Charlotte
    Besset, Tatiana
    Poisson, Thomas
    Pannecoucke, Xavier
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (37) : 12836 - 12865
  • [5] Berberan-Santos MN., 2012, MOL FLUORESCENCE, DOI DOI 10.1002/9783527650002
  • [6] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
    Charpentier, Julie
    Frueh, Natalja
    Togni, Antonio
    [J]. CHEMICAL REVIEWS, 2015, 115 (02) : 650 - 682
  • [7] Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis
    Chatterjee, Tanmay
    Iqbal, Naeem
    You, Youngmin
    Cho, Eun Jin
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) : 2284 - 2294
  • [8] Trifluoromethylation of Alkenes with Concomitant Introduction of Additional Functional Groups
    Egami, Hiromichi
    Sodeoka, Mikiko
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) : 8294 - 8308
  • [9] Photochemistry and photophysics of coordination compounds: Iridium
    Flamigni, Lucia
    Barbieri, Andrea
    Sabatini, Cristiana
    Ventura, Barbara
    Barigelletti, Francesco
    [J]. PHOTOCHEMISTRY AND PHOTOPHYSICS OF COORDINATION COMPOUNDS II, 2007, 281 : 143 - 203
  • [10] Visible-light-mediated radical oxydifluoromethylation of olefinic amides for the synthesis of CF2H-containing heterocycles
    Fu, Weijun
    Han, Xin
    Zhu, Mei
    Xu, Chen
    Wang, Zhiqiang
    Ji, Baoming
    Hao, Xin-Qi
    Song, Mao-Ping
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (91) : 13413 - 13416
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