Rhodium Catalyzed, Carbon-Hydrogen Bond Directed Hydrodefluorination of Fluoroarenes

被引:30
|
作者
Ekkert, Olga [1 ]
Strudley, Sebastian D. A. [1 ]
Rozenfeld, Alisa [1 ]
White, Andrew J. P. [1 ]
Crimmin, Mark R. [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
基金
英国工程与自然科学研究理事会;
关键词
C-F ACTIVATION; FLUORINE BONDS; H BONDS; COMPLEXES; HEXAFLUOROBENZENE; FLUOROAROMATICS; SELECTIVITY; CRYSTAL; HYDRIDE;
D O I
10.1021/om501113j
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
[Cp*RhCl(mu-Cl)](2) is reported as a highly efficient and selective precatalyst for the hydrodefluorination of perfluoroarenes using a hydrocarbon-soluble aluminum dihydride as the terminal reductant. Reactions are directed to cleave a C-F bond adjacent to an existing C-H bond with high regioselectivity (98.5-99%). A heterobimetallic complex containing an extremely rare Al-H-Rh functional group has been isolated and shown to be catalytically competent.
引用
收藏
页码:7027 / 7030
页数:4
相关论文
共 50 条
  • [31] Base-promoted carbon-hydrogen bond activation of alkanes with rhodium(III) porphyrin complexes
    Chan, Yun Wai
    Chan, Kin Shing
    ORGANOMETALLICS, 2008, 27 (18) : 4625 - 4635
  • [32] KINETICS OF TERMINAL ALKYNE SP CARBON-HYDROGEN BOND ACTIVATION CATALYZED BY SILVER (I)
    LEWANDOS, GS
    MAKI, JW
    GINNEBAUGH, JP
    ORGANOMETALLICS, 1982, 1 (12) : 1700 - 1705
  • [33] Rhodium-catalyzed silylation of aromatic carbon-hydrogen bonds in 2-arylpyridines with disilane
    Tobisu, Mamoru
    Ano, Yusuke
    Chatani, Naoto
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1585 - 1591
  • [34] Rhodium-Catalyzed Synthesis of Silafluorene Derivatives via Cleavage of Silicon-Hydrogen and Carbon-Hydrogen Bonds
    Ureshino, Tomonari
    Yoshida, Takuya
    Kuninobu, Yoichiro
    Takai, Kazuhiko
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) : 14324 - 14326
  • [35] Rhodium catalyzed hydrogenation of fluoroarenes in mild condition
    Dick, Tyler
    Luke, Anna
    Peterson, Alicia
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [36] Activation of the carbon-hydrogen bond by oxides and halides
    Metiu, Horia
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [37] The carbon-hydrogen bond strengths in methane and ethane
    Andersen, HG
    Kistiakowsky, CB
    Van Artsdalen, ER
    JOURNAL OF CHEMICAL PHYSICS, 1942, 10 (05): : 305 - 305
  • [38] CARBON-HYDROGEN BOND DISSOCIATION ENERGY IN METHANOL
    CRUICKSHANK, FR
    BENSON, SW
    JOURNAL OF PHYSICAL CHEMISTRY, 1969, 73 (03): : 733 - +
  • [39] Activation of the carbon-hydrogen bond by oxides and halides
    Metiu, Horia
    Chretien, Steeve
    Kristoffersen, Henrik
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [40] Combined Rhodium-Catalyzed Carbon-Hydrogen Activation and β-Carbon Elimination to access Eight-Membered Rings
    Crepin, Damien
    Dawick, James
    Aissa, Christophe
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (03) : 620 - 623