Highly β(Z)-Selective Hydrosilylation of Terminal Alkynes Catalyzed by Thiolate-Bridged Dirhodium Complexes

被引：32
|
作者：
Zhao, Xiangyu [1 ]
Yang, Dawei [1 ]
Zhang, Yahui [1 ]
Wang, Baomin [1 ]
Qu, Jingping [1 ,2 ]
机构：
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] East China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 17期
基金：
中国国家自然科学基金;
关键词：
N-HETEROCYCLIC CARBENE; Z-SELECTIVE HYDROSILYLATION; STEREOSELECTIVE HYDROSILYLATION; CP-ASTERISK; RUTHENIUM COMPLEXES; (Z)-SELECTIVE HYDROSILYLATION; MARKOVNIKOV HYDROSILYLATION; RHODIUM(I) COMPLEXES; HYDRIDE COMPLEXES; NICKEL-IRON;
D O I：
10.1021/acs.orglett.8b02267
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of novel monothiolate-bridged dirhodium complexes, [Cp*Rh(mu-SR)(mu-Cl)(2)RhCp*][BF4] {Cp* = eta(5)-C5Me5, R = tertiary butyl (Bu-t), 1a; R = ferrocenyl (Fc), 1b; R = adamantyl (Ad), 1c} were designed and successfully synthesized, which can smoothly facilitate highly regioselective and stereoselective hydrosilylation of terminal alkynes to afford beta(Z) vinylsilanes with good functional group compatibility. Furthermore, the hydride bridged dirhodium complex [Cp*Rh(mu-(SBu)-Bu-t)(mu-Cl)(mu-H)RhCp*][BF4] (5) as a potential inter-mediate was obtained by the reaction of la with excess HSiEt3.
引用
收藏
页码：5357 / 5361
页数：5
相关论文
共 50 条
  • [1] Head-to-head Z dimerization of terminal alkynes catalyzed by thiolate-bridged diruthenium complexes
    Qü, JP
    Masui, D
    Ishii, Y
    Hidai, M
    [J]. CHEMISTRY LETTERS, 1998, (10) : 1003 - 1004
  • [2] Cobalt-Catalyzed Z-Selective Hydrosilylation of Terminal Alkynes
    Teo, Wei Jie
    Wang, Chao
    Tan, Ye Wei
    Ge, Shaozhong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) : 4328 - 4332
  • [3] Pincer cobalt complex-catalyzed Z-selective hydrosilylation of terminal alkynes
    Du, Xiaoyong
    Hou, Wenjun
    Zhang, Yanlu
    Huang, Zheng
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (08): : 1517 - 1521
  • [4] Three Reversible Redox States of Thiolate-Bridged Dirhodium Complexes without Metal-Metal Bonds
    Coll, Ryan P.
    Dunbar, Kim R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (38) : 16313 - 16323
  • [5] Highly β-(E)-selective hydrosilylation of terminal and internal alkynes catalyzed by a (IPr)Pt(diene) complex
    Berthon-Gelloz, Guillaume
    Schumers, Jean-Marc
    De Bo, Guillaume
    Marko, Istvan E.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (11): : 4190 - 4197
  • [6] Allylation of arenes catalysed by thiolate-bridged diruthenium complexes
    Nishibayashi, Y
    Yamanashi, M
    Takagi, Y
    Hidai, M
    [J]. CHEMICAL COMMUNICATIONS, 1997, (09) : 859 - 860
  • [7] Hydration of Nitriles to Amides by Thiolate-Bridged Diiron Complexes
    Tong, Peng
    Yang, Dawei
    Li, Yang
    Wang, Baomin
    Qu, Jingping
    [J]. ORGANOMETALLICS, 2015, 34 (14) : 3571 - 3576
  • [8] Cyclization of terminal diynes catalyzed by thiolate-bridged diruthenium complexes:: A simple synthetic route to endo-macrocyclic (Z)-1-en-3-ynes
    Nishibayashi, Y
    Yamanashi, M
    Wakiji, I
    Hidai, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (16) : 2909 - 2911
  • [9] Thiolate-bridged heterobimetallic complexes as electrocatalysts for proton reduction
    Ghosh, Pokhraj
    Wang, Ning
    Ding, Shengda
    Bhuvanesh, Nattamai
    Popescu, Victoria
    Hall, Michael
    Darensbourg, Marcetta
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [10] Catalytic disproportionation of hydrazine by thiolate-bridged diiron complexes
    Su, Linan
    Yang, Dawei
    Wang, Baomin
    Qu, Jingping
    [J]. INORGANIC CHEMISTRY COMMUNICATIONS, 2020, 112
12345