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
  • [21] Asymmetric Intramolecular Carbocyanation of Alkenes by C-C Bond Activation
    Najera, Carmen
    Sansano, Jose M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (14) : 2452 - 2456
  • [22] Reversible Boron-Insertion into Aromatic C-C Bonds
    Kuroki, Kaito
    Ito, Tatsuyoshi
    Takaya, Jun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (48)
  • [23] Heterogeneous Iron-Catalyzed Aerobic Oxidative Cleavage of C-C Bonds in Alcohols to Esters
    Tan, Shangzhi
    Yu, Xiangzhu
    Zhu, Lina
    Fu, Weiru
    Wang, Lianyue
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2022, 10 (50) : 16527 - 16537
  • [24] Mild Oxidation of C-C Bonds of Benzoiridacycles
    Padilla, Rosa
    Salazar, Veronica
    Paneque, Margarita
    Alvarado-Rodriguez, Jose G.
    Tamariz, Joaquin
    Pacheco-Cuvas, Hector
    Vattier, Florencia
    ORGANOMETALLICS, 2010, 29 (12) : 2835 - 2838
  • [25] Copper-catalyzed C-C bond cleavage and intramolecular cyclization: an approach toward acridones
    Zhou, Wang
    Yang, Youqing
    Liu, Yong
    Deng, Guo-Jun
    GREEN CHEMISTRY, 2013, 15 (01) : 76 - 80
  • [26] Synthetic transformation of C-H and C-C bonds
    Murakami, M
    Ito, Y
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (05) : 444 - 451
  • [27] Selective Cleavage and Tunable Functionalization of the C-C/C-N Bonds of N-Arylpiperidines Promoted by tBuONO
    He, Yan
    Zheng, Zhi
    Liu, Yajie
    Qiao, Jiajie
    Zhang, Xinying
    Fan, Xuesen
    ORGANIC LETTERS, 2019, 21 (06) : 1676 - 1680
  • [28] Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes
    Shen, Tong
    Liu, Shuai
    Zhao, Jianyou
    Wang, Nengyong
    Yang, Le
    Wu, Jintao
    Shen, Xu
    Liu, Zhong-Quan
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (05) : 3286 - 3295
  • [29] Progress of the C-C Bond Cleavage in Acetonitrile Catalyzed by Transition-Metal Complexes
    Chen Hui-Qing
    Zhang Kun
    Xu Feng
    Huang Wei
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2013, 29 (11) : 2265 - 2275
  • [30] Transition-Metal-Mediated Cleavage of C-C Single Bonds: Making the Cut in Total Synthesis
    Wang, Brian
    Perea, Melecio A.
    Sarpong, Richmond
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (43) : 18898 - 18919