Regio- and Stereoselective Copper(II)-Catalyzed Hydrosilylation of Activated Allenes in Water: Access to Vinylsilanes

被引:30
|
作者
Pashikanti, Srinath [1 ]
Calderone, Joseph A. [1 ]
Nguyen, Matthew K. [1 ]
Sibley, Christopher D. [1 ]
Santos, Webster L. [1 ]
机构
[1] Virginia Tech, Dept Chem, Blacksburg, VA 24061 USA
基金
美国国家科学基金会;
关键词
SI-B BOND; SILYL CONJUGATE ADDITIONS; INTERNAL ALKYNES; TERMINAL ALKYNES; CATALYZED HYDROSILYLATION; REGIOSELECTIVE HYDROSILYLATION; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; BETA-BORYLATION; GAMMA-ADDITIONS;
D O I
10.1021/acs.orglett.6b00981
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By using catalytic amounts of copper(II), 4-picoline, and dimethylphenylsilylpinacol borane, a series of allenoates were silylated on the beta carbon in good to excellent yields and high (E)-selectivity. The mild and efficient silylation method is conducted in water under atmospheric conditions to afford vinylsilanes.
引用
收藏
页码:2443 / 2446
页数:4
相关论文
共 50 条
  • [1] Copper(II)-catalyzed highly regio- and stereoselective hydrosilylation of unactivated internal alkynes with silylborate in water
    Xuan, Qing-Qing
    Ren, Chuan-Li
    Liu, Li
    Wang, Dong
    Li, Chao-Jun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (21) : 5871 - 5874
  • [2] Regio- and stereoselective hydrosilylation of alkynes with alkoxysilanes for the synthesis of β-(Z) vinylsilanes catalyzed by a dirhodium(ii)/XantPhos complex
    Yang, Liqun
    Lu, Wenkui
    Wu, Xiaoyu
    Lu, Yan
    Xie, Xiaomin
    Zhang, Zhaoguo
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (02) : 448 - 457
  • [3] Copper(I)-Catalyzed Regio- and Stereoselective Silaboration of Terminal Allenes
    Ozawa, Yu
    Koriyama, Hisao
    Shiratori, Yuma
    Ito, Hajime
    [J]. ACS ORGANIC & INORGANIC AU, 2023, 3 (02): : 104 - 108
  • [4] Copper-catalyzed regio- and stereo-selective hydrosilylation of terminal allenes to access (E)-allylsilanes
    Shaowei Chen
    Xiaoqian He
    Yi Jin
    Yu Lan
    Xiao Shen
    [J]. Nature Communications, 13
  • [5] Copper-catalyzed regio- and stereo-selective hydrosilylation of terminal allenes to access (E)-allylsilanes
    Chen, Shaowei
    He, Xiaoqian
    Jin, Yi
    Lan, Yu
    Shen, Xiao
    [J]. NATURE COMMUNICATIONS, 2022, 13 (01)
  • [6] Iron-Catalyzed Synthesis of (E)-β-Vinylsilanes via a Regio- and Stereoselective Hydrosilylation from Terminal Alkynes
    Liu, Zhi-Kai
    Zhang, Guo-Liang
    Li, Ding-Chang
    Yang, Ying
    Chen, Li
    Zhan, Zhuang-Ping
    [J]. SYNLETT, 2019, 30 (02) : 235 - 239
  • [7] Copper(I)-Catalyzed Highly Regio- and Stereoselective Hydrosilylation of Terminal Alkynes with Boryldisiloxane
    Zhou, Hui
    Wang, Yan-Bo
    [J]. CHEMCATCHEM, 2014, 6 (09) : 2512 - 2516
  • [8] Cobalt-Catalyzed Regio- and Stereoselective Hydroboration of Allenes
    Li, Can
    Yang, Zheng
    Wang, Lei
    Guo, Yinlong
    Huang, Zheng
    Ma, Shengming
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (15) : 6278 - 6283
  • [9] Regio- and Stereoselective Oxysulfonylation of Allenes
    Huang, Zhiyuan
    Lu, Qingquan
    Liu, Yichang
    Liu, Dong
    Zhang, Jian
    Lei, Aiwen
    [J]. ORGANIC LETTERS, 2016, 18 (16) : 3940 - 3943
  • [10] Experimental and Computational Studies of the Ruthenium-Catalyzed Hydrosilylation of Alkynes: Mechanistic Insights into the Regio- and Stereoselective Formation of Vinylsilanes
    Gao, Ruili
    Pahls, Dale R.
    Cundari, Thomas R.
    Yi, Chae S.
    [J]. ORGANOMETALLICS, 2014, 33 (23) : 6937 - 6944