Copper-catalyzed Sila-Sonogashira-Hagihara Cross-coupling Reactions of Alkynylsilanes with Aryl Iodides under Palladium-free Conditions

被引：38
|
作者：
Nishihara, Yasushi [1 ]
Noyori, Shintaro [1 ]
Okamoto, Takeru [1 ]
Suetsugu, Masato [1 ]
Iwasaki, Masayuki [1 ]
机构：
[1] Okayama Univ, Div Chem & Biochem, Grad Sch Nat Sci & Technol, Kita Ku, Okayama 7008530, Japan
来源：
CHEMISTRY LETTERS | 2011年 / 40卷 / 09期
关键词：
HETEROARYL HALIDES; TERMINAL ALKYNES; SALT; POLYCONDENSATION; ACETYLENES; CHLORIDES; ALKENYL; TOLANES; KETONES;
D O I：
10.1246/cl.2011.972
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient and inexpensive catalytic system using a readily available CuCl/PPh3 combination for the catalytic cross-coupling reactions of alkynylsilanes with a variety of aryl iodides affords unsymmetrical diarylethynes in good to excellent yields.
引用
收藏
页码：972 / 974
页数：3
相关论文
共 50 条
  • [1] Palladium-free copper-catalyzed Sonogashira cross-coupling at room temperature
    Liang, Huimin
    Fu, Hua
    Qiao, Renzhong
    Jiang, Yuyang
    Zhao, Yufen
    [J]. SYNTHESIS-STUTTGART, 2008, (15): : 2417 - 2426
  • [2] Copper-catalyzed sonogashira-type reactions under mild palladium-free conditions
    Monnier, Florian
    Turtaut, Francois
    Duroure, Leslie
    Taillefer, Marc
    [J]. ORGANIC LETTERS, 2008, 10 (15) : 3203 - 3206
  • [3] Palladium/copper-catalyzed sila-Sonogashira reactions of aryl iodides with alkynylsilanes via a direct C-Si bond activation
    Nishihara, Yasushi
    Inoue, Eiji
    Ogawa, Daisuke
    Okada, Yoshiaki
    Noyori, Shintaro
    Takagi, Kentaro
    [J]. TETRAHEDRON LETTERS, 2009, 50 (32) : 4643 - 4646
  • [4] Sila-Sonogashira Cross-Coupling Reactions of Activated Aryl Chlorides with Alkynylsilanes
    Nishihara, Yasushi
    Inoue, Eiji
    Okada, Yoshiaki
    Takagi, Kentaro
    [J]. SYNLETT, 2008, (19) : 3041 - 3045
  • [5] Synthesis of unsymmetrically disubstituted ethynes by the palladium/copper(I)-cocatalyzed sila-Sonogashira-Hagihara coupling reactions of alkynylsilanes with aryl iodides, bromides, and chlorides through a direct activation of a carbon-silicon bond
    Nishihara, Yasushi
    Inoue, Eiji
    Noyori, Shintaro
    Ogawa, Daisuke
    Okada, Yoshiaki
    Iwasaki, Masayuki
    Takagi, Kentaro
    [J]. TETRAHEDRON, 2012, 68 (24) : 4869 - 4881
  • [6] Cu(I)/Pd(0)-catalyzed cross-coupling reaction of alkynylsilanes with aryl or alkenyl triflates: "Sila"-Sonogashira-Hagihara coupling
    Nishihara, Y
    Ikegashira, K
    Mori, A
    Hiyama, T
    [J]. CHEMISTRY LETTERS, 1997, (12) : 1233 - 1234
  • [7] Palladium-free copper-catalyzed coupling reaction of aryl iodides and terminal acetylenes in water
    Chen, Gong
    Zhu, Xinhai
    Cai, Jiwen
    Wan, Yiqian
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) : 1355 - 1361
  • [8] Synthesis of Unsymmetrical Diarylethynes by Pd(0)/Cu(I)-cocatalyzed Sila-Sonogashira-Hagihara Coupling Reactions of Alkynylsilanes with Aryl Tosylates or Mesylates
    Nishihara, Yasushi
    Ogawa, Daisuke
    Noyori, Shintaro
    Iwasaki, Masayuki
    [J]. CHEMISTRY LETTERS, 2012, 41 (11) : 1503 - 1505
  • [9] Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides under Ligand-Free Conditions
    Huang, Yu-Ting
    Tsai, Wan-Ting
    Badsara, Satpal Singh
    Chan, Chien-Ching
    Lee, Chin-Fa
    [J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2014, 61 (09) : 967 - 974
  • [10] Copper-catalyzed cross-coupling of aryl acetylenes and vinyl iodides
    Venkataraman, D
    Bates, CG
    Saejueng, P
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U118 - U118
12345