Pd-catalyzed Highly Regio- and Stereocontrolled Direct Alkenylation of Electron-deficient Polyfluoroarenes

被引：19
作者：
Chen, Fei [1 ]
Zhang, Xingang [1 ]
机构：
[1] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
来源：
CHEMISTRY LETTERS | 2011年 / 40卷 / 09期
关键词：
C-H BOND; OXIDATIVE HECK REACTION; DIRECT ARYLATION; SIMPLE ARENES; F BOND; PERFLUOROARENES; ACTIVATION; FLUORINE; OLEFINATION; METATHESIS;
D O I：
10.1246/cl.2011.978
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An effective and reliable method for Pd-catalyzed highly regio- and stereocontrolled direct alkenylation of electron-deficient polyfluoroarenes with alkenyl iodides has been developed. The advantages of this reaction are its high regio- and stereoselectivity, mild reaction temperature (70 degrees C), and the use of readily available Pd(PPh3)(4). This approach provides a useful access to polyfluoroarylated derivatives of interest in both life and materials science.
引用
收藏
页码：978 / 979
页数：2
相关论文
共 32 条
  • [1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [2] Mechanism of silver-promoted ligand metathesis in square-planar complexes of d8 ions.: Kinetics of formation and molecular structures of a trinuclear intermediate [(Me)(N-N)Pt(μ-Cl)Ag(μ-Cl)Pt(N-N)(Me)]+ and its dinuclear evolution product [(Me)(N-N)Pt(μ-Cl)Pt(N-N)(Me)]+ (N-N = ArN=C(Me)C(Me)=NAr, Ar=2,6-(i-Pr)2C6H3)
    Albano, VG
    Di Serio, M
    Monari, M
    Orabona, I
    Panunzi, A
    Ruffo, F
    [J]. INORGANIC CHEMISTRY, 2002, 41 (10) : 2672 - 2677
  • [3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [4] C-F Bond Activation in Organic Synthesis
    Amii, Hideki
    Uneyama, Kenji
    [J]. CHEMICAL REVIEWS, 2009, 109 (05) : 2119 - 2183
  • [5] Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom
    Babudri, Francesco
    Farinola, Gianluca M.
    Naso, Francesco
    Ragni, Roberta
    [J]. CHEMICAL COMMUNICATIONS, 2007, (10) : 1003 - 1022
  • [6] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules
    Campeau, LC
    Fagnou, K
    [J]. CHEMICAL COMMUNICATIONS, 2006, (12) : 1253 - 1264
  • [7] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
    Colby, Denise A.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. CHEMICAL REVIEWS, 2010, 110 (02) : 624 - 655
  • [8] Regioselective functionalization of unreactive carbon-hydrogen bonds
    Daugulis, Olafs
    Zaitsev, Vladimir G.
    Shabashov, Dmitry
    Pham, Quynh-Nhu
    Lazareva, Anna
    [J]. SYNLETT, 2006, (20) : 3382 - 3388
  • [9] A general and highly selective chelate-controlled intermolecular oxidative Heck reaction
    Delcamp, Jared H.
    Brucks, Alexandria P.
    White, M. Christina
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) : 11270 - +
  • [10] A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds
    Do, Hien-Ouang
    Khan, Rana M. Kashif
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) : 15185 - 15192
1234