New Horizons of Photocatalytic Fluoromethylative Difunctionalization of Alkenes

被引:235
作者
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
CHEM | 2018年 / 4卷 / 03期
关键词
LIGHT PHOTOREDOX CATALYSIS; ELECTRON-DEFICIENT ALKENES; TRANSFER RADICAL-ADDITION; CARBON MULTIPLE BONDS; VISIBLE-LIGHT; UNACTIVATED ALKENES; TRIFLUOROMETHYLATION REACTIONS; DIASTEREOSELECTIVE SYNTHESIS; FLUOROALKYLSULFONYL CHLORIDES; FLUOROALKYLATION REACTIONS;
D O I
10.1016/j.chempr.2017.11.004
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Radical tri- and difluoromethylation (fluoromethylation) by photoredox catalysis has emerged as a new synthetic methodology over the past several years. In particular, the strategy is useful for the introduction of a fluoromethyl group (CF2X, X = F or H) and a different functional group across a carbon-carbon double bond via a single operation. Step-economical synthesis of diverse organofluorine compounds bearing a C(sp(3))-CF2X bond has been achieved. In this review, the discussion focuses on recent representative examples of photoredox-catalyzed fluoromethylative difunctionalization of alkenes through redox-neutral processes. Close attention is paid to the choice of the fluorome-thylating reagent and the photocatalyst. The basic concept, reaction design, and the prospects for this research area are also discussed.
引用
收藏
页码:409 / 437
页数:29
相关论文
共 101 条
  • [1] OUTER-SPHERE DISSOCIATIVE ELECTRON-TRANSFER TO ORGANIC-MOLECULES - A SOURCE OF RADICALS OR CARBANIONS - DIRECT AND INDIRECT ELECTROCHEMISTRY OF PERFLUOROALKYL BROMIDES AND IODIDES
    ANDRIEUX, CP
    GELIS, L
    MEDEBIELLE, M
    PINSON, J
    SAVEANT, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) : 3509 - 3520
  • [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] Trifluoromethylchlorosulfonylation of Alkenes: Evidence for an Inner-Sphere Mechanism by a Copper Phenanthroline Photoredox Catalyst
    Bagal, Dattatraya B.
    Kachkovskyi, Georgiy
    Knorn, Matthias
    Rawner, Thomas
    Bhanage, Bhalchandra M.
    Reiser, Oliver
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) : 6999 - 7002
  • [4] Photocatalytic fluoroalkylation reactions of organic compounds
    Barata-Vallejo, Sebastian
    Bonesi, Sergio M.
    Postigo, Al
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11153 - 11183
  • [5] A scalable and operationally simple radical trifluoromethylation
    Beatty, Joel W.
    Douglas, James J.
    Cole, Kevin P.
    Stephenson, Corey R. J.
    [J]. NATURE COMMUNICATIONS, 2015, 6
  • [6] DIFLUOROIODOMETHANE - PRACTICAL SYNTHESIS AND REACTION WITH ALKENES
    CAO, P
    DUAN, JX
    CHEN, QY
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) : 737 - 738
  • [7] Three-Component Photoredox-Mediated Chloro-, Bromo-, or Iodotrifluoromethylation of Alkenes
    Carboni, Aude
    Dagousset, Guillaume
    Magnier, Emmanuel
    Masson, Geraldine
    [J]. SYNTHESIS-STUTTGART, 2015, 47 (16): : 2439 - 2445
  • [8] One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis
    Carboni, Aude
    Dagousset, Guillaume
    Magnier, Emmanuel
    Masson, Geraldine
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (91) : 14197 - 14200
  • [9] Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates
    Carboni, Aude
    Dagousset, Guillaume
    Magnier, Emmanuel
    Masson, Geraldine
    [J]. ORGANIC LETTERS, 2014, 16 (04) : 1240 - 1243
  • [10] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
    Charpentier, Julie
    Frueh, Natalja
    Togni, Antonio
    [J]. CHEMICAL REVIEWS, 2015, 115 (02) : 650 - 682