Palladium-Catalyzed Carbon-Fluorine and Carbon-Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes

被引：23
|
作者：
Chen, Wenyi [1 ]
Hooper, Thomas N. [1 ]
Ng, Jamues [1 ]
White, Andrew J. P. [1 ]
Crimmin, Mark R. [1 ]
机构：
[1] Imperial Coll London, Dept Chem, London SW7 2AZ, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 41期
基金：
欧盟地平线“2020”; 欧洲研究理事会;
关键词：
alumination; C-F activation; C-H activation; fluoroarenes; hydrodefluorination; C-F ACTIVATION; OXIDATIVE ADDITION; BUILDING-BLOCKS; MEDICINAL CHEMISTRY; C(SP(3))-F BONDS; HYDRODEFLUORINATION; FUNCTIONALIZATION; RHODIUM; BORYLATION; CLEAVAGE;
D O I：
10.1002/anie.201706378
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Through serendipitous discovery, a palladium bis(phosphine) complex was identified as a catalyst for the selective transformation of sp(2)C-F and sp(2)C-H bonds of fluoroarenes and heteroarenes to sp(2)C-Al bonds (19 examples, 1 mol% Pd loading). The carbon-fluorine bond functionalization reaction is highly selective for the formation of organoaluminium products in preference to hydrodefluorination products (selectivity=4.4:1 to 27:1). Evidence is presented for a tandem catalytic process in which hydrodefluorination is followed by sp(2)C-H alumination.
引用
收藏
页码：12687 / 12691
页数：5
相关论文
共 50 条
  • [1] Palladium-catalyzed aliphatic carbon-fluorine bond formation
    Katcher, Matthew H.
    Doyle, Abigail G.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [2] Rhodium Catalyzed, Carbon-Hydrogen Bond Directed Hydrodefluorination of Fluoroarenes
    Ekkert, Olga
    Strudley, Sebastian D. A.
    Rozenfeld, Alisa
    White, Andrew J. P.
    Crimmin, Mark R.
    [J]. ORGANOMETALLICS, 2014, 33 (24) : 7027 - 7030
  • [3] Palladium-catalyzed fluorination of carbon-hydrogen bonds
    Hull, Kami L.
    Anani, Waseem Q.
    Sanford, Melanie S.
    [J]. Journal of the American Chemical Society, 2006, 128 (22): : 7134 - 7135
  • [4] Palladium-catalyzed fluorination of carbon-hydrogen bonds
    Hull, Kami L.
    Anani, Waseem Q.
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) : 7134 - 7135
  • [5] Carbon-fluorine bond activation coupled with carbon-hydrogen bond formation α to iridium:: Kinetics, mechanism, and diastereoselectivity
    Garratt, SA
    Hughes, RP
    Kovacik, I
    Ward, AJ
    Willemsen, S
    Zhang, DH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) : 15585 - 15594
  • [6] Solvent effects on the carbon-fluorine hydrogen bond
    Rosenberg, Robert E.
    Huu Nguyen
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [7] Palladium(0)-Catalyzed Carbon-Hydrogen Bond Functionalization for the Synthesis of Indoloquinazolinones
    Tsukano, Chihiro
    Okuno, Masataka
    Nishiguchi, Hiromi
    Takemoto, Yoshiji
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1533 - 1538
  • [8] Synthesis of Methylene-Bridge Polyarenes through Palladium-Catalyzed Activation of Benzylic Carbon-Hydrogen Bond
    Hsiao, Chien-Chi
    Lin, Yi-Kuan
    Liu, Chia-Ju
    Wu, Tsun-Cheng
    Wu, Yao-Ting
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3267 - 3274
  • [9] A STUDY OF CARBON-FLUORINE BOND
    RAJPUT, AS
    PANDEY, GK
    CHANDRA, S
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (10) : 2424 - +
  • [10] Carbon-fluorine bond formation
    Furuya, Takeru
    Kuttruff, Christian A.
    Ritter, Tobias
    [J]. CURRENT OPINION IN DRUG DISCOVERY & DEVELOPMENT, 2008, 11 (06) : 803 - 819
12345