Fluoride-catalyzed three-component coupling reaction of a silylphosphine, activated alkenes and aldehydes

被引:21
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
关键词
silylphosphine; phosphination; Michael addition; three-component coupling;
D O I
10.1016/j.tetlet.2005.05.128
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel CsF-catalyzed three-component coupling reaction of a silylphosphine, activated alkenes and aldehydes is described. Multi-functional phosphines were obtained by forming both carbon-phosphorus and carbon-carbon bonds in good yields under mild conditions. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5135 / 5138
页数:4
相关论文
共 18 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]  
[Anonymous], 1995, COMPREHENSIVE ORGANO, DOI DOI 10.1016/B978-008046519-7.00134-9
[3]  
BORDACHEV AA, 1994, IZV AKAD NAUK K, V4, P754
[4]   t-BuOK-catalyzed addition phosphines to functionalized alkenes:: a convenient synthesis of polyfunctional phosphine derivatives [J].
Bunlaksananusorn, T ;
Knochel, P .
TETRAHEDRON LETTERS, 2002, 43 (33) :5817-5819
[5]   ADDITION OF GERMYLPHOSPHINES AND SILYLPHOSPHINES TO ALPHA-ETHYLENIC ALDEHYDES AND KETONES [J].
COURET, C ;
ESCUDIE, J ;
SATGE, J ;
ANH, NT ;
SOUSSAN, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 91 (01) :11-30
[6]   Fluoride-mediated phosphination of alkenes and alkynes by silylphosphines [J].
Hayashi, M ;
Matsuura, Y ;
Watanabe, Y .
TETRAHEDRON LETTERS, 2004, 45 (50) :9167-9169
[7]   Activation of silylphosphines by diethyl azodicarboxylate: novel silylation of alcohols [J].
Hayashi, M ;
Matsuura, Y ;
Watanabe, Y .
TETRAHEDRON LETTERS, 2004, 45 (07) :1409-1411
[8]   Boron trifluoride-mediated alkylation of diphenylphosphine with tert-alkyl fluoride [J].
Hirano, K ;
Yorimitsu, H ;
Oshima, K .
ORGANIC LETTERS, 2004, 6 (26) :4873-4875
[9]   Highly stereoselective addition of silylphosphines to chiral aldehydes [J].
Kolodiazhnyi, OI ;
Guliaiko, IV ;
Kolodiazhna, AO .
TETRAHEDRON LETTERS, 2004, 45 (37) :6955-6957
[10]   Regio- and stereoselective hydrophosphination reactions of alkynes with phosphine-boranes: Access to stereodefined vinylphosphine derivatives [J].
Mimeau, D ;
Gaumont, AC .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7016-7022