A new transformation of silanols. Palladium-catalyzed cross-coupling with organic halides in the presence of silver(I) oxide

被引:162
作者
Hirabayashi, K [1 ]
Kawashima, J [1 ]
Nishihara, Y [1 ]
Mori, A [1 ]
Hiyama, T [1 ]
机构
[1] Tokyo Inst Technol, Resources Utilizat Res Lab, Yokohama, Kanagawa 2268503, Japan
关键词
D O I
10.1021/ol990614c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The reactions of aryl- and alkenylsilanols with organic halides are found to proceed in a catalyst system of 5 mol % of Pd(PPh3)(4) and Ag2O (1 equiv) to give the corresponding coupling products in up to 84% yield.
引用
收藏
页码:299 / 301
页数:3
相关论文
共 23 条
  • [1] Base promoted preparation of alkenylsilanols from allylsilanes
    Akiyama, T
    Imazeki, S
    [J]. CHEMISTRY LETTERS, 1997, (10) : 1077 - 1078
  • [2] ENANTIOSELECTIVE SYNTHESIS OF EPOXIDES VIA SHARPLESS EPOXIDATION OF ALKENYLSILANOLS
    CHAN, TH
    CHEN, LM
    WANG, D
    LI, LH
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1993, 71 (01): : 60 - 67
  • [3] ENANTIOSELECTIVE SYNTHESIS OF EPOXIDES - SHARPLESS EPOXIDATION OF ALKENYLSILANOLS
    CHAN, TH
    CHEN, LM
    WANG, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (19) : 1280 - 1281
  • [4] GILLMANN T, 1994, SYNLETT, P649
  • [5] SELECTIVE SYNTHESIS OF UNSYMMETRICAL BIARYLS VIA PALLADIUM-CATALYZED CROSS-COUPLING OF ARYLFLUOROSILANES WITH ARYL IODIDES
    HATANAKA, Y
    FUKUSHIMA, S
    HIYAMA, T
    [J]. CHEMISTRY LETTERS, 1989, (10) : 1711 - 1714
  • [6] HATANAKA Y, 1989, J ORG CHEM, V54, P265
  • [7] Synthesis of cyclopropylsilanols by the Simmons-Smith reaction of alkenylsilanols and lithium alkenylsilanolates
    Hirabayashi, K
    Mori, A
    Hiyama, T
    [J]. TETRAHEDRON LETTERS, 1997, 38 (03) : 461 - 464
  • [8] A novel C-C bond forming reaction of aryl- and alkenylsilanols. A halogen-free Mizoroki-Heck type reaction
    Hirabayashi, K
    Nishihara, Y
    Mori, A
    Hiyama, T
    [J]. TETRAHEDRON LETTERS, 1998, 39 (43) : 7893 - 7896
  • [9] A facile preparation and cyclopropanation of 1-alkenylsilanols
    Hirabayashi, K
    Takahisa, E
    Nishihara, Y
    Mori, A
    Hiyama, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (10) : 2409 - 2417
  • [10] PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ORGANOMETALLOIDS THROUGH ACTIVATION WITH FLUORIDE-ION
    HIYAMA, T
    HATANAKA, Y
    [J]. PURE AND APPLIED CHEMISTRY, 1994, 66 (07) : 1471 - 1478