Activation of silylphosphines by diethyl azodicarboxylate: novel silylation of alcohols

被引:28
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; silylation; silyl ether;
D O I
10.1016/j.tetlet.2003.12.053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel activation mode of silylphosphines and an application of that to silylation of alcohols were described. Silylphosphines were found to be instantly activated by means of DEAD and PPTS to form reactive silyl cation equivalents. By using the activated species, silylation of alcohols successfully proceeded under mild acidic condition. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1409 / 1411
页数:3
相关论文
共 9 条
[1]   REACTIONS OF SILICON-PHOSPHORUS BOND .I. INSERTIONS IN TRIMETHYLSILYLDIPHENYLPHOSPHINE [J].
ABEL, EW ;
SABHERWA.IH .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (05) :1105-&
[2]  
BORDACHEV AA, 1994, IZV AKAD NAUK K, P756
[3]   Silylphosphanes: Developments in phosphorus chemistry [J].
Fritz, G ;
Scheer, P .
CHEMICAL REVIEWS, 2000, 100 (09) :3341-3401
[4]  
Greene T. W., 1999, PROTECTIVE GROUPS OR, P113
[5]  
Hughes D.L., 1992, ORG REACT, V42, P335, DOI DOI 10.1002/0471264180.OR042.02
[6]   REACTIONS OF ACID-CHLORIDES WITH TRIMETHYLSILYLDIPHENYLPHOSPHINE .11. SYNTHESIS AND PROPERTIES OF AROMATIC ACID PHOSPHIDES [J].
KUNZEK, H ;
BRAUN, M ;
NESENER, E ;
RUHLMANN, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 49 (01) :149-156
[7]  
Luther III G. W., 1977, INORG SYNTH, V17, P186, DOI DOI 10.1002/9780470132487.CH51
[8]  
THOTTATHIL J, 1992, HDB ORGANOPHOSPHORUS, P84
[9]   PALLADIUM-CATALYZED COUPLING OF ARYL HALIDES WITH (TRIMETHYLSTANNYL)DIPHENYLPHOSPHINE AND (TRIMETHYLSILYL)DIPHENYLPHOSPHINE [J].
TUNNEY, SE ;
STILLE, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :748-753