From vinyl sulfides, sulfoxides and sulfones to vinyl zirconocene derivatives

被引:52
|
作者
Farhat, S [1 ]
Zouev, I [1 ]
Marek, I [1 ]
机构
[1] Technion Israel Inst Technol, Dept Chem, Inst Catalysis Sci & Technol, IL-32000 Haifa, Israel
基金
以色列科学基金会;
关键词
D O I
10.1016/j.tet.2003.08.074
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An easy and straightforward new method for the preparation of Sp(2) zirconocene derivatives from a wide range of heterosubstituted alkenes such as vinyl sulfides, sulfoxides and sulfones is described. In all cases, a complete isomerization of the stereochemistry is observed and only the E-isomer is obtained. The reactivity of the resulting vinylic organometallic can be increased by a transmetalation reaction into organocopper, organozinc or organopalladium species and, therefore, several carbon-carbon formation were easily realized. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1329 / 1337
页数:9
相关论文
共 50 条
  • [1] From vinyl sulfides, sulfoxides, and sulfones to vinyl transition metal complexes
    Farhat, S
    Marek, I
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (08) : 1410 - 1413
  • [2] Stereoselective Heck Reactions with Vinyl Sulfoxides, Sulfides and Sulfones
    Bachmann, Daniel G.
    Wittwer, Christopher C.
    Gillingham, Dennis G.
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3703 - 3707
  • [3] ORGANOSILICON VINYL SULFOXIDES AND VINYL SULFONES
    SHOSTAKO.MF
    KOMAROV, NV
    VLASOVA, NN
    RINKUS, GA
    JOURNAL OF GENERAL CHEMISTRY USSR, 1966, 36 (05): : 917 - &
  • [4] Metal catalysed hydroboration of vinyl sulfides, sulfoxides, sulfones, and sulfonates
    Webb, Jonathan D.
    Harrison, Daniel J.
    Norman, David W.
    Blacquiere, Johanna M.
    Vogels, Christopher M.
    Decken, Andreas
    Bates, Craig G.
    Venkataraman, D.
    Baker, R. Thomas
    Westcott, Stephen A.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 275 (1-2) : 91 - 100
  • [5] CYCLOPROPANATION OF VINYL SULFIDES AND VINYL SULFONES
    LIEBOWITZ, SM
    JOHNSON, HJ
    SYNTHETIC COMMUNICATIONS, 1986, 16 (10) : 1255 - 1259
  • [6] Recent applications of vinyl sulfones and vinyl sulfoxides in asymmetric synthesis
    Carretero, JC
    Arrayás, RG
    Buezo, ND
    Garrido, JL
    Alonso, I
    Adrio, J
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 153 : 259 - 273
  • [8] Synthesis of β-trifluoroacetyl-substituted vinyl sulfones and vinyl sulfides
    Krasovsky, AL
    Nenajdenko, VG
    Balenkova, ES
    RUSSIAN CHEMICAL BULLETIN, 2002, 51 (11) : 2080 - 2085
  • [9] Synthesis of β-trifluoroacetyl-substituted vinyl sulfones and vinyl sulfides
    A. L. Krasovsky
    V. G. Nenajdenko
    E. S. Balenkova
    Russian Chemical Bulletin, 2002, 51 : 2080 - 2085
  • [10] CONTRASTING PATHWAYS FOR THE DIRECTED HOMOGENEOUS HYDROGENATION OF VINYL SULFOXIDES AND VINYL SULFONES
    ANDO, D
    BEVAN, C
    BROWN, JM
    PRICE, DW
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (08) : 592 - 594