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
来源：
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 02期
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
  • [41] Novel Pd(II)- and Pt(II)-catalyzed regio- and stereoselective trans-hydroarylation of alkynes by simple arenes
    Jia, CG
    Lu, WJ
    Oyamada, J
    Kitamura, T
    Matsuda, K
    Irie, M
    Fujiwara, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) : 7252 - 7263
  • [42] Lewis acid catalyzed highly regio- and stereocontrolled trans-hydrosilylation of alkynes and allenes
    Sudo, T
    Asao, N
    Gevorgyan, V
    Yamamoto, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07): : 2494 - 2499
  • [43] Copper (II)-catalyzed regio- and stereoselective addition of H/P(O)R2 to alkynes
    Trostyanskaya, Inna G.
    Beletskaya, Irina P.
    [J]. TETRAHEDRON, 2014, 70 (15) : 2556 - 2562
  • [44] Ruthenium-catalyzed hydrosilylation of 1-alkynes with novel regio- and stereoselectivity.
    Yamamoto, K
    Kawanami, Y
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U571 - U571
  • [45] Ruthenium(II)-Catalyzed Regio- and Stereoselective Hydroarylation of Alkynes via Directed C-H Functionalization
    Hashimoto, Yuto
    Hirano, Koji
    Satoh, Tetsuya
    Kakiuchi, Fumitoshi
    Miura, Masahiro
    [J]. ORGANIC LETTERS, 2012, 14 (08) : 2058 - 2061
  • [46] Highly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes
    Dupuy, Stephanie
    Gasperini, Danila
    Nolan, Steven P.
    [J]. ACS Catalysis, 2015, 5 (11): : 6918 - 6921
  • [47] Palladium-Catalyzed Regio- and Stereoselective Chlorothiolation of Terminal Alkynes with Sulfenyl Chlorides
    Iwasaki, Masayuki
    Fujii, Tomoya
    Yamamoto, Arisa
    Nakajima, Kiyohiko
    Nishihara, Yasushi
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (01) : 58 - 62
  • [48] Regio- and stereoselective dimerization of terminal alkynes to enynes catalyzed by a palladium/imidazolium system
    Yang, CL
    Nolan, SP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02): : 591 - 593
  • [49] Recent Advances in Cobalt-Catalyzed Regio- or Stereoselective Hydrofunctionalization of Alkenes and Alkynes
    Li, Yan
    Lu, Xi
    Fu, Yao
    [J]. CCS CHEMISTRY, 2024, 6 (05): : 1130 - 1156
  • [50] Palladium-Catalyzed Regio- and Stereoselective Carbothiolation of Terminal Alkynes with Azolyl Sulfides
    Iwasaki, Masayuki
    Topolovcan, Nikola
    Hu, Hao
    Nishimura, Yugo
    Gagnot, Glwadys
    Nakorn, Rungsaeng Na
    Yuvacharaskul, Ramida
    Nakajima, Kiyohiko
    Nishihara, Yasushi
    [J]. ORGANIC LETTERS, 2016, 18 (07) : 1642 - 1645
12345