Copper-Catalyzed Silacarboxylation of Internal Alkynes by Employing Carbon Dioxide and Silylboranes

被引:138
作者
Fujihara, Tetsuaki [1 ]
Tani, Yosuke [1 ]
Semba, Kazuhiko [1 ]
Terao, Jun [1 ]
Tsuji, Yasushi [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Kyoto 6158510, Japan
关键词
alkynes; carboxylation; copper; homogeneous catalysis; silylborane; C-H BONDS; DIRECT CARBOXYLATION; TERMINAL ALKYNES; PALLADIUM; HYDROCARBOXYLATION; SILABORATION; COMPLEXES; CLEAVAGE; TRANSFORMATION; BENZOSILOLES;
D O I
10.1002/anie.201207148
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Silalactones: The copper-catalyzed reaction of internal alkynes with (dimethylphenylsilyl)pinacolborane (Me 2PhSi-B(pin)) as the silicon source and CO 2 at atmospheric pressure afforded silalactones selectively in good to high yields. The silalactones can be used as substrates for the Hiyama cross-coupling reaction as demonstrated for one substrate. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11487 / 11490
页数:4
相关论文
共 51 条
  • [1] [Anonymous], 2010, ANGEW CHEM-GER EDIT
  • [2] [Anonymous], 2010, ANGEW CHEM
  • [3] [Anonymous], 2011, ANGEW CHEM-GER EDIT
  • [4] [Anonymous], 2011, ANGEW CHEM-GER EDIT
  • [5] Aresta M., 2010, CARBON DIOXIDE CHEM
  • [6] Iridium-Catalyzed Preparation of Silylboranes by Silane Borylation and Their Use in the Catalytic Borylation of Arenes
    Boebel, Timothy A.
    Hartwig, John F.
    [J]. ORGANOMETALLICS, 2008, 27 (22) : 6013 - 6019
  • [7] Carboxylation of N-H/C-H Bonds Using N-Heterocyclic Carbene Copper(I) Complexes
    Boogaerts, Ine I. F.
    Fortman, George C.
    Furst, Marc R. L.
    Cazin, Catherine S. J.
    Nolan, Steven P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) : 8674 - 8677
  • [8] Carboxylation of C-H Bonds Using N-Heterocyclic Carbene Gold(I) Complexes
    Boogaerts, Ine I. F.
    Nolan, Steven P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) : 8858 - +
  • [9] Structural and spectroscopic studies on three-coordinate complexes of copper(I) halides with tricyclohexylphosphine
    Bowmaker, GA
    Boyd, SE
    Hanna, JV
    Hart, RD
    Healy, PC
    Skelton, BW
    White, AH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (13): : 2722 - 2730
  • [10] Cokoja M., 2011, ANGEW CHEM, V123, P8662, DOI DOI 10.1002/ANGE.201102010