Boron trifluoride-catalyzed reaction of alkyl fluoride with silyl enolate, allylsilane, and hydrosilane

被引:58
作者
Hirano, K [1 ]
Fujita, K [1 ]
Yorimitsu, H [1 ]
Shinokubo, H [1 ]
Oshima, K [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
基金
日本学术振兴会;
关键词
alkyl fluoride; alkylation; silyl enolate; boron trifluoride; silane;
D O I
10.1016/j.tetlet.2004.01.145
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkylation of silyl enolates with tert-alkyl or allylic fluorides proceeds smoothly in the presence of a catalytic amount of boron trifluoride to afford the corresponding carbonyl compounds. Allylation and reduction of alkyl fluorides with allylsilane and hydrosilane, respectively, occur under BF3 catalysis. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2555 / 2557
页数:3
相关论文
共 5 条
[1]   HETEROGENEOUS FLUORINATION OF ALLYLIC HALIDES BY THE COMBINATION OF LEAD FLUORIDE AND A SODIUM-SALT [J].
ICHIHARA, J ;
TAKAI, Y ;
HANAFUSA, T ;
TOMIOKA, K .
JOURNAL OF FLUORINE CHEMISTRY, 1995, 71 (01) :131-133
[2]   SYNTHETIC METHODS AND REACTIONS .63. PYRIDINIUM POLY-(HYDROGEN FLUORIDE) (30-PERCENT PYRIDINE 70-PERCENT HYDROGEN-FLUORIDE) - CONVENIENT REAGENT FOR ORGANIC FLUORINATION REACTIONS [J].
OLAH, GA ;
WELCH, JT ;
VANKAR, YD ;
NOJIMA, M ;
KEREKES, I ;
OLAH, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3872-3881
[3]   Organoaluminum-catalyzed new alkylation of tert-alkyl fluorides: Synthetic utility of Al-F interaction [J].
Ooi, T ;
Uraguchi, D ;
Kagoshima, N ;
Maruoka, K .
TETRAHEDRON LETTERS, 1997, 38 (32) :5679-5682
[4]   LEWIS ACID MEDIATED ALPHA-ALKYLATION OF CARBONYL-COMPOUNDS .6. OPTIMIZATION OF THE PROCEDURE FOR THE ALPHA-TERT-ALKYLATION OF KETONES AND ALDEHYDES [J].
REETZ, MT ;
MAIER, WF ;
HEIMBACH, H ;
GIANNIS, A ;
ANASTASSIOUS, G .
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (12) :3734-3740
[5]   LEWIS ACID-INDUCED ALPHA-ALKYLATION OF CARBONYL-COMPOUNDS [J].
REETZ, MT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1982, 21 (02) :96-108