Cleavage of C-C and C-Si σ-Bonds and Their Intramolecular Exchange

被引:120
|
作者
Ishida, Naoki [1 ]
Ikemoto, Wataru [1 ]
Murakami, Masahiro [1 ]
机构
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
关键词
CARBON-CARBON BOND; NICKEL-CATALYZED CARBOCYANATION; COUPLING REACTIONS; PALLADIUM; SILACYCLOBUTANES; ACTIVATION; METHYLENECYCLOPROPANES; CHEMISTRY; BIPHENYLENE; PLATINUM;
D O I
10.1021/ja502601g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
C-C and C-Si sigma-bonds are cleaved to undergo bond exchange when substrates equipped with cyclobutanone and silacyclobutane moieties are treated with a palladium(0) catalyst. The skeletal exchange results in construction of silabicyclo[5.2.1]decanes in a diastereoselective manner.
引用
收藏
页码:5912 / 5915
页数:4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Intermolecular Exchange between C-C and C-Si σ-Bonds
    Okumura, Shintaro
    Sun, Fangzhu
    Ishida, Naoki
    Murakami, Masahiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (36) : 12414 - 12417
  • [2] Cobalt-catalyzed intramolecular decarbonylative coupling of acylindoles and diarylketones through the cleavage of C-C bonds
    Yu, Tian-Yang
    Xu, Wen-Hua
    Lu, Hong
    Wei, Hao
    CHEMICAL SCIENCE, 2020, 11 (45) : 12336 - 12340
  • [3] Metal-mediated cleavage of unsaturated C-C bonds
    Chan, Antony P. Y.
    Sergeev, Alexey G.
    COORDINATION CHEMISTRY REVIEWS, 2020, 413
  • [4] Transition-Metal-Mediated Cleavage of C-C Bonds in Aromatic Rings
    Jakoobi, Martin
    Sergeev, Alexey G.
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (13) : 2181 - 2192
  • [5] Enantioselective Cross-Exchange between C-I and C-C σ Bonds
    Sun, Yu-Li
    Wang, Xing-Ben
    Sun, Feng-Na
    Chen, Qian-Qian
    Cao, Jian
    Xu, Zheng
    Xu, Li-Wen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (20) : 6747 - 6751
  • [6] Scandium triflate catalyzed unexpected cleavage of C-C bonds in ynones
    Kavthe, Rahul D.
    Bansode, Avinash H.
    Patil, Nitin T.
    ARKIVOC, 2016, : 223 - 232
  • [7] Intramolecular C-C agostic complexes: C-C sigma interactions by another name
    Etienne, Michel
    Weller, Andrew S.
    CHEMICAL SOCIETY REVIEWS, 2014, 43 (01) : 242 - 259
  • [8] Transition-Metal-Mediated Cleavage and Activation of C-C Single Bonds
    Ruhland, Klaus
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (14) : 2683 - 2706
  • [9] Selective Hydroboration of C-C Single Bonds without Transition-Metal Catalysis
    Li, Sida
    Hu, Chaopeng
    Leo Liu, Liu
    Wu, Lipeng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (51)
  • [10] Cobalt-Catalyzed Regioselective Carboamidation of Alkynes with Imides Enabled by Cleavage of C-N and C-C Bonds
    Min, Xiang-Ting
    Ji, Ding-Wei
    Zheng, Hao
    Chen, Bing-Zhi
    Hu, Yan-Cheng
    Wan, Boshun
    Chen, Qing-An
    ORGANIC LETTERS, 2020, 22 (09) : 3386 - 3391