Stereoselective syntheses of (E)-1-boryl-3-(silyl)propenes via ruthenium-catalyzed cross-metathesis and cross-coupling reactions

被引：19
|
作者：
Jankowska, Magdalena
Pietraszuk, Cezary
Marciniec, Bogdan [1 ]
Zaidlewicz, Marek
机构：
[1] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
[2] Nicholas Copernicus Univ, Dept Chem, PL-87100 Torun, Poland
来源：
SYNLETT | 2006年 / 11期
关键词：
silylative coupling; cross-metathesis; organic synthesis; organosilicon compounds; organoboron compounds;
D O I：
10.1055/s-2006-944212
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general and mostly highly stereoselective method for effective synthesis of 1-boryl-3-(silyl)propenes via one-step catalytic processes, i.e. silylative coupling of vinylsilanes with allyl boronates, borylative coupling of vinyl boronates with allylsilanes catalysed by [RuHCl(CO)(PCy3)(2)] and cross-metathesis of respective derivatives in the presence of Grubbs catalysts, is described.
引用
收藏
页码：1695 / 1698
页数：4
相关论文
共 50 条
  • [1] Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis
    Ferré-Filmon, K
    Delaude, L
    Demonceau, A
    Noels, AF
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (15) : 3319 - 3325
  • [2] Ruthenium-catalyzed olefin cross metathesis of styrenes as an alternative to the Heck and cross-coupling reactions
    Chatterjee, AK
    Toste, FD
    Choi, TL
    Grubbs, RH
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (6-7) : 634 - 637
  • [3] Ruthenium-Catalyzed Sequential Enyne Cross-Metathesis/ATRA Reactions
    Kiefer, Gregor
    Ruiz, Jesus
    Solari, Euro
    Hilt, Gerhard
    Severin, Kay
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (01) : 93 - 98
  • [4] Functionalization of octavinylsilsesquioxane by ruthenium-catalyzed silylative coupling versus cross-metathesis
    Itami, Y
    Marciniec, B
    Kubicki, M
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (05) : 1239 - 1248
  • [5] Straightforward synthesis of α,β-unsaturated thioesters via ruthenium-catalyzed olefin cross-metathesis with thioacrylate
    van Zijl, Anthoni W.
    Minnaard, Adriaan J.
    Feringa, Ben L.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5651 - 5653
  • [6] Stereoselective synthesis of esters with vinylsilicon functionality via ruthenium carbene catalyzed cross-metathesis
    Kujawa-Welten, M
    Marciniec, B
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 190 (1-2) : 79 - 83
  • [7] Photoinduced ruthenium-catalyzed alkyl-alkyl cross-coupling reactions
    Jana, Sripati
    Pei, Chao
    Bahukhandi, Srishti Ballabh
    Koenigs, Rene M.
    CHEM CATALYSIS, 2021, 1 (02): : 467 - 479
  • [8] Ruthenium-catalyzed cross-coupling reactions between ketones and primary amines
    Cho, Chan Sik
    CATALYSIS COMMUNICATIONS, 2006, 7 (12) : 1012 - 1014
  • [9] Synthesis of tri-substituted vinyl boronates via ruthenium-catalyzed olefin cross-metathesis
    Morrill, C
    Funk, TW
    Grubbs, RH
    TETRAHEDRON LETTERS, 2004, 45 (41) : 7733 - 7736
  • [10] Terminal conjugated dienes via a ruthenium-catalyzed cross-metathesis/elimination sequence: application to renewable resources
    Bilel, Hallouma
    Hamdi, Naceur
    Zagrouba, Fethi
    Fischmeister, Cedric
    Bruneau, Christian
    CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (07) : 2064 - 2071
12345