New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust

被引:157
作者
Fillon, H [1 ]
Gosmini, C [1 ]
Périchon, J [1 ]
机构
[1] Univ Paris 12, UMR 7582 CNRS, Lab Electrochim Catalyze & Syth Organ, F-94320 Thiais, France
关键词
D O I
10.1021/ja0289494
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new chemical method for the preparation of arylzinc intermediates is described in acetonitrile, on the basis of the activation of aryl bromides by low-valent cobalt species arising from the reduction of cobalt halide by zinc dust. This procedure allows for the synthesis of a variety of functionalized aryl- and thienylzinc species in good to excellent yields. The versatility and the simplicity of that original method represent an alternative to most known procedures.
引用
收藏
页码:3867 / 3870
页数:4
相关论文
共 23 条
  • [1] Boudier A, 2000, ANGEW CHEM INT EDIT, V39, P4414, DOI 10.1002/1521-3773(20001215)39:24<4414::AID-ANIE4414>3.0.CO
  • [2] 2-C
  • [3] Preparation of alternating π-conjugated copolymers involving electrochemically generated aryldizinc intermediates
    Cecile, C
    Mellah, M
    Labbé, E
    Nédélec, JY
    Périchon, J
    [J]. NEW JOURNAL OF CHEMISTRY, 2002, 26 (06) : 787 - 790
  • [4] Pure acetonitrile as solvent for the efficient electrochemical conversion of aryl bromides in organozinc species and their coupling reaction with acetyl chloride
    Fillon, H
    Le Gall, E
    Gosmini, C
    Périchon, J
    [J]. TETRAHEDRON LETTERS, 2002, 43 (34) : 5941 - 5944
  • [5] Electrosynthesis of functionalized organodizinc compounds from aromatic dihalides via a cobalt catalysis in acetonitrile/pyridine as solvent
    Fillon, H
    Gosmini, C
    Nédélec, JY
    Périchon, J
    [J]. TETRAHEDRON LETTERS, 2001, 42 (23) : 3843 - 3846
  • [6] FILLON H, 2001, Patent No. 0108880
  • [7] Synthesis of unsymmetrical biaryls by electroreductive cobalt-catalyzed cross-coupling of aryl halides
    Gomes, P
    Fillon, H
    Gosmini, C
    Labbé, E
    Périchon, J
    [J]. TETRAHEDRON, 2002, 58 (42) : 8417 - 8424
  • [8] Electrosynthesis of 3-thienylzinc bromide from 3-bromothiophene via a nickel catalysis.
    Gosmini, C
    Nedelec, JY
    Perichon, J
    [J]. TETRAHEDRON LETTERS, 1997, 38 (11) : 1941 - 1942
  • [9] New efficient preparation of arylzinc compounds from aryl halides using cobalt catalysis and sacrificial anode process
    Gosmini, C
    Rollin, Y
    Nédélec, JY
    Périchon, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 6024 - 6026
  • [10] Preparation of unsymmetrical biaryls via palladium-catalyzed coupling reaction of aryl halides
    Hassan, J
    Hathroubi, C
    Gozzi, C
    Lemaire, M
    [J]. TETRAHEDRON, 2001, 57 (37) : 7845 - 7855