Fluoride-mediated phosphination of alkenes and alkynes by silylphosphines

被引：31
作者：
Hayashi, M [1 ]
Matsuura, Y [1 ]
Watanabe, Y [1 ]
机构：
[1] Ehime Univ, Fac Engn, Dept Appl Chem, Matsuyama, Ehime 7908577, Japan
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 50期
关键词：
silylphosphine; phosphination; Michael addition; three-component coupling;
D O I：
10.1016/j.tetlet.2004.10.098
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselective phosphination of carbon-carbon unsaturated bonds by a fluoride-mediated reaction of silylphosphines is described. Alkenes and alkynes having a directing group, such as an aromatic or a carbonyl group, reacted to form a carbon-phosphorus bond under mild conditions. When an anhydrous fluoride source was applied in the presence of an electrophile, the corresponding three-component coupling product was obtained. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9167 / 9169
页数：3
相关论文
共 18 条
  • [1] ABEL EN, 1999, APPL TRANSITION META, V9
  • [2] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
  • [3] ADDITION OF DIPHENYLPHOSPHINE TO MICHAEL-TYPE OLEFINS - THE PREPARATION OF PHOSPHINE-NITRILE AND PHOSPHINE-ESTER LIGANDS
    BLINN, DA
    BUTTON, RS
    FARAZI, V
    NEEB, MK
    TAPLEY, CL
    TREHEARNE, TE
    WEST, SD
    KRUGER, TL
    STORHOFF, BN
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 393 (01) : 143 - 152
  • [4] BORDACHEV AA, 1994, IZV AKAD NAUK K, V4, P754
  • [5] t-BuOK-catalyzed addition phosphines to functionalized alkenes:: a convenient synthesis of polyfunctional phosphine derivatives
    Bunlaksananusorn, T
    Knochel, P
    [J]. TETRAHEDRON LETTERS, 2002, 43 (33) : 5817 - 5819
  • [6] ADDITION OF GERMYLPHOSPHINES AND SILYLPHOSPHINES TO ALPHA-ETHYLENIC ALDEHYDES AND KETONES
    COURET, C
    ESCUDIE, J
    SATGE, J
    ANH, NT
    SOUSSAN, G
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 91 (01) : 11 - 30
  • [7] Silylphosphanes: Developments in phosphorus chemistry
    Fritz, G
    Scheer, P
    [J]. CHEMICAL REVIEWS, 2000, 100 (09) : 3341 - 3401
  • [8] Gilheany D. G., 1990, CHEM ORGANOPHOSPHORU, V1, P151
  • [9] Activation of silylphosphines by diethyl azodicarboxylate: novel silylation of alcohols
    Hayashi, M
    Matsuura, Y
    Watanabe, Y
    [J]. TETRAHEDRON LETTERS, 2004, 45 (07) : 1409 - 1411
  • [10] Highly stereoselective addition of silylphosphines to chiral aldehydes
    Kolodiazhnyi, OI
    Guliaiko, IV
    Kolodiazhna, AO
    [J]. TETRAHEDRON LETTERS, 2004, 45 (37) : 6955 - 6957
12