Pd-Catalyzed Oxidative Cross-Coupling of Perfluoroarenes with Aromatic Heterocycles

被引:271
作者
He, Chun-Yang [1 ]
Fan, Shilu [1 ]
Zhang, Xingang [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
关键词
C-H FUNCTIONALIZATION; THIN-FILM TRANSISTORS; DIRECT ARYLATION; ORGANIC SEMICONDUCTORS; ARENES; OLIGOFLUOROBENZENES; OLIGOTHIOPHENES; DERIVATIVES; ACTIVATION; MECHANISM;
D O I
10.1021/ja106046p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A straightforward and practical method for direct Pd(OAc)(2)-catalyzed oxidative cross-coupling of electron-deficient perfluoroarenes with aromatic heterocycles has been developed. Because of its low catalyst loading (2.5 mol %), high reaction efficiency, good chemo- and regioselectivity, and excellent functional-group compatibility, this protocol provides a useful and operationally simple access to perfluoroarene thiophene structures of interest in functional materials for electronic devices.
引用
收藏
页码:12850 / 12852
页数:3
相关论文
共 40 条
  • [1] C-F Bond Activation in Organic Synthesis
    Amii, Hideki
    Uneyama, Kenji
    [J]. CHEMICAL REVIEWS, 2009, 109 (05) : 2119 - 2183
  • [2] 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
  • [3] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides
    Brasche, Gordon
    Garcia-Fortanet, Jorge
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2008, 10 (11) : 2207 - 2210
  • [4] Hexyl-substituted oligothiophenes with a central tetrafluorophenylene unit: crystal engineering of planar structures for p-type organic semiconductors
    Crouch, DJ
    Skabara, PJ
    Heeney, M
    McCulloch, I
    Coles, SJ
    Hursthouse, MB
    [J]. CHEMICAL COMMUNICATIONS, 2005, (11) : 1465 - 1467
  • [5] 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
  • [6] Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) : 1128 - +
  • [7] An Aromatic Glaser-Hay Reaction
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (47) : 17052 - +
  • [8] Copper-catalyzed arene C-H bond cross-coupling
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. CHEMICAL COMMUNICATIONS, 2009, (42) : 6433 - 6435
  • [9] C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls
    Dwight, Timothy A.
    Rue, Nicholas R.
    Charyk, Dagmara
    Josselyn, Ryan
    DeBoef, Brenton
    [J]. ORGANIC LETTERS, 2007, 9 (16) : 3137 - 3139
  • [10] Building blocks for n-type organic electronics: Regiochemically modulated inversion of majority carrier sign in perfluoroarene-modified polythiophene semiconductors
    Facchetti, A
    Yoon, MH
    Stern, CL
    Katz, HE
    Marks, TJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) : 3900 - 3903