Regio- and stereoselective hydrosilylation of alkynes with alkoxysilanes for the synthesis of β-(Z) vinylsilanes catalyzed by a dirhodium(ii)/XantPhos complex

被引:3
|
作者
Yang, Liqun [1 ]
Lu, Wenkui [1 ]
Wu, Xiaoyu [1 ]
Lu, Yan [1 ]
Xie, Xiaomin [1 ]
Zhang, Zhaoguo [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
N-HETEROCYCLIC CARBENE; ANTI-MARKOVNIKOV HYDROSILYLATION; Z-SELECTIVE HYDROSILYLATION; TRANSITION-METAL-COMPLEXES; C-H FUNCTIONALIZATION; TERMINAL ALKYNES; REGIOSELECTIVE HYDROSILYLATION; RHODIUM(I) COMPLEXES; RUTHENIUM COMPLEXES; ENANTIOSELECTIVE SYNTHESIS;
D O I
10.1039/d3qo01725g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Rh2(OAc)(4)/XantPhos ((9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane)) catalyzed regio- and stereoselective hydrosilylation of alkynes with various tertiary silanes in acetonitrile represents a straightforward and highly effective strategy for the synthesis of beta-(Z) vinylsilanes. This method exhibits remarkable compatibility with diverse functional groups, encompassing halides, nitriles, amines, esters, nitro compounds, and heterocycles.
引用
收藏
页码:448 / 457
页数:10
相关论文
共 50 条
  • [1] 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
  • [2] Regio- and Stereoselective Copper(II)-Catalyzed Hydrosilylation of Activated Allenes in Water: Access to Vinylsilanes
    Pashikanti, Srinath
    Calderone, Joseph A.
    Nguyen, Matthew K.
    Sibley, Christopher D.
    Santos, Webster L.
    [J]. ORGANIC LETTERS, 2016, 18 (10) : 2443 - 2446
  • [3] 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
  • [4] Highly Regio- and Stereoselective Hydrosilylation of Alkynes Catalyzed by Tridentate Cobalt Complexes
    Kong, Degong
    Hu, Bowen
    Chen, Dafa
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (15) : 2694 - 2703
  • [5] Regio- and stereoselective hydrosilylation of immobilized terminal alkynes
    Pedersen, Palle J.
    Henriksen, Jonas
    Gotfredsen, Charlotte H.
    Clausen, Mads H.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (43) : 6220 - 6223
  • [6] 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
  • [7] Xantphos Doped POPs-PPh3 as Heterogeneous Ligand for Cobalt-Catalyzed Highly Regio- and Stereoselective Hydrosilylation of Alkynes
    Li, Ren-Hao
    Zhang, Guo-Liang
    Dong, Jia-Xing
    Li, Ding-Chang
    Yang, Ying
    Pan, Ying-Ming
    Tang, Hai-Tao
    Chen, Li
    Zhan, Zhuang-Ping
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (01) : 149 - 154
  • [8] Regio- and stereoselective synthesis of (Z)-vinylgermanes by hydrogermylation of alkynes
    David-Quillot, Frank
    Thiery, Valerie
    Abarbri, Mohamed
    Thibonnet, Jerome
    Besson, Thierry
    Duchene, Alain
    [J]. MAIN GROUP METAL CHEMISTRY, 2007, 30 (05) : 235 - 244
  • [9] Palladium-Catalyzed Regio- and Stereoselective Hydrosilylation of Electron-Deficient Alkynes
    Sumida, Yuto
    Kato, Tomoe
    Yoshida, Suguru
    Hosoya, Takamitsu
    [J]. ORGANIC LETTERS, 2012, 14 (06) : 1552 - 1555
  • [10] 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