Highly Efficient Incorporation of Functional Groups into Aromatic Main-Chain Polymer Using Iridium-Catalyzed C-H Activation and Suzuki-Miyaura Reaction

被引:72
作者
Jo, Tae Soo [1 ]
Kim, Se Hye [1 ]
Shin, Jihoon [1 ]
Bae, Chulsung [1 ]
机构
[1] Univ Nevada, Dept Chem, Las Vegas, NV 89154 USA
基金
美国国家科学基金会;
关键词
CROSS-COUPLING REACTIONS; POLYSULFONES; BORYLATION; MEMBRANES; ARENES; SYSTEMS;
D O I
10.1021/ja808374e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a mild, iridium-catalyzed borylation of aromatic polysulfone with bis(pinacolato)diboron [B-2(pin)(2)] to form the corresponding borylated polysulfones up to high concentrations with nearly constant efficiency. The Suzuki-Miyaura cross-coupling reactions of the borylated polysulfones with functionalized aryl bromides allows installation of various functional groups such as ketone, amine, hydroxyl, and aldehyde to the polysulfone main chain in excellent conversion.
引用
收藏
页码:1656 / +
页数:3
相关论文
共 22 条
  • [1] Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes
    Boller, TM
    Murphy, JM
    Hapke, M
    Ishiyama, T
    Miyaura, N
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) : 14263 - 14278
  • [2] SYNTHESIS AND CHARACTERIZATION OF PENDANTLY AMINE FUNCTIONALIZED POLY(ARYLENE ETHER SULFONE)
    BOTTINO, FA
    MAMO, A
    RECCA, A
    BRADY, J
    STREET, AC
    MCGRAIL, PT
    [J]. POLYMER, 1993, 34 (13) : 2901 - 2902
  • [3] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds
    Cho, JY
    Tse, MK
    Holmes, D
    Maleczka, RE
    Smith, MR
    [J]. SCIENCE, 2002, 295 (5553) : 305 - 308
  • [4] Sterically directed functionalization of aromatic C-H bonds: Selective borylation ortho to cyano groups in arenes and heterocycles
    Chotana, GA
    Rak, MA
    Smith, MR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) : 10539 - 10544
  • [5] THE MODIFICATION OF POLYSULFONE BY METALATION
    GUIVER, MD
    APSIMON, JW
    KUTOWY, O
    [J]. JOURNAL OF POLYMER SCIENCE PART C-POLYMER LETTERS, 1988, 26 (02) : 123 - 127
  • [6] FUNCTIONAL-GROUP POLYSULFONES BY BROMINATION METALATION
    GUIVER, MD
    KUTOWY, O
    APSIMON, JW
    [J]. POLYMER, 1989, 30 (06) : 1137 - 1142
  • [7] Guiver MD, 2001, J POLYM SCI POL CHEM, V39, P2103
  • [8] Guiver MD, 2000, ACS SYM SER, V744, P137
  • [9] Poly(arylene ether sulfone) copolymers and related systems from disulfonated monomer building blocks: Synthesis, characterization, and performance - A topical review
    Harrison, WL
    Hickner, MA
    Kim, YS
    McGrath, JE
    [J]. FUEL CELLS, 2005, 5 (02) : 201 - 212
  • [10] Alternative polymer systems for proton exchange membranes (PEMs)
    Hickner, MA
    Ghassemi, H
    Kim, YS
    Einsla, BR
    McGrath, JE
    [J]. CHEMICAL REVIEWS, 2004, 104 (10) : 4587 - 4611