Hydrodehalogenation of organohalides by Et3SiH catalysed by group 4 metal complexes and B(C6F5)3

被引:11
作者
Dunlop, David [1 ]
Pinkas, Jiri [1 ]
Horacek, Michal [1 ]
Zilkova, Nadezda [1 ]
Lamac, Martin [1 ]
机构
[1] Czech Acad Sci, J Heyrovsky Inst Phys Chem, Vvi, Dolejskova 2155-3, Prague 18223 8, Czech Republic
关键词
F BOND ACTIVATION; SI-H; HYDRODEFLUORINATION; TRIFLUOROTOLUENES; CHEMISTRY; CLEAVAGE;
D O I
10.1039/d0dt00360c
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Catalytic hydrodehalogenation (HDH) of aliphatic organohalides such as trifluorotoluenes by Et3SiH proceeds in the presence of readily available group 4 metal compounds: Cp ' 2MX2 (Cp ' = eta(5)-C5H5 or eta(5)-C5Me5; X = F, Cl, or Me; M = Ti, Zr, or Hf), CpTiCl3 and TiCl4 with a catalytic amount of B(C6F5)(3). The use of metallocenes in combination with the borane activator leads to a better selectivity of the reaction, i.e., suppression of Friedel-Crafts alkylations of arenes.
引用
收藏
页码:2771 / 2775
页数:5
相关论文
共 38 条
  • [1] Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation To Access Fluorinated Building Blocks
    Ahrens, Theresia
    Kohlmann, Johannes
    Ahrens, Mike
    Braun, Thomas
    [J]. CHEMICAL REVIEWS, 2015, 115 (02) : 931 - 972
  • [2] Hydrodefluorinations of trifluorotoluenes by LiAlH4 and TiCl4
    Akiyama, Takahiko
    Atobe, Kohei
    Shibata, Michiko
    Mori, Keiji
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 : 81 - 83
  • [3] C-F Bond Activation in Organic Synthesis
    Amii, Hideki
    Uneyama, Kenji
    [J]. CHEMICAL REVIEWS, 2009, 109 (05) : 2119 - 2183
  • [4] [Anonymous], 2012, ANGEW CHEM
  • [5] Reactions of zirconocene 2-vinylpyridine complexes with diisobutylaluminum hydride and fluoride
    Arndt, P
    Spannenberg, A
    Baumann, W
    Burlakov, VV
    Rosenthal, U
    Becke, S
    Weiss, T
    [J]. ORGANOMETALLICS, 2004, 23 (20) : 4792 - 4795
  • [6] Activation of Alkyl C-F Bonds by B(C6F5)3: Stoichiometric and Catalytic Transformations
    Caputo, Christopher B.
    Stephan, Douglas W.
    [J]. ORGANOMETALLICS, 2012, 31 (01) : 27 - 30
  • [7] Activation of C-F Bonds by Electrophilic Organosilicon Sites Supported on Sulfated Zirconia
    Culver, Damien B.
    Conley, Matthew P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (45) : 14902 - 14905
  • [8] Hydrodefluorination of perfluoroalkyl groups using silylium-carborane catalysts
    Douvris, Christos
    Ozerov, Oleg V.
    [J]. SCIENCE, 2008, 321 (5893) : 1188 - 1190
  • [9] Hydrodefluorination and Other Hydrodehalogenation of Aliphatic Carbon-Halogen Bonds Using Silylium Catalysis
    Douvris, Christos
    Nagaraja, C. M.
    Chen, Chun-Hsing
    Foxman, Bruce M.
    Ozerov, Oleg V.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (13) : 4946 - 4953
  • [10] SILANE REDUCTIONS IN ACIDIC MEDIA .7. ALUMINUM-CHLORIDE CATALYZED HYDROGEN-HALOGEN EXCHANGE BETWEEN ORGANOSILANES AND ALKYL-HALIDES - EFFICIENT HYDROCARBON SYNTHESIS
    DOYLE, MP
    MCOSKER, CC
    WEST, CT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) : 1393 - 1396