Activation of tetrabutylammonium hydrogen difluoride with pyridine: A mild and efficient procedure for nucleophilic fluorination

被引:30
作者
Moughamir, K
Atmani, A
Mestdagh, H
Rolando, C
Francesch, C
机构
[1] Ecole Normale Super, Dept Chim, CNRS, F-75231 Paris 05, France
[2] Univ Sidi Mohamed Ben Abdellah, Fac Sci, Chim Organ Lab, Fes 30000, Morocco
[3] IUFM Paris, F-75016 Paris, France
关键词
D O I
10.1016/S0040-4039(98)01564-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The nucleophilic fluorination of alkyl iodides, bromides and tosylates and of alpha-bromo- or alpha-chloroketones is smoothly effected by tetrabutylammonium hydrogen difluoride in the presence of pyridine, in dioxane or THF, with good or satisfying substitution-to-elimination ratio. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7305 / 7306
页数:2
相关论文
共 10 条
[1]   TETRABUTYLAMMONIUM BIFLUORIDE - A VERSATILE AND EFFICIENT FLUORINATING AGENT [J].
BOSCH, P ;
CAMPS, F ;
CHAMORRO, E ;
GASOL, V ;
GUERRERO, A .
TETRAHEDRON LETTERS, 1987, 28 (40) :4733-4736
[2]   NUCLEOPHILIC FLUORINE DISPLACEMENT-REACTIONS - A COMPARISON OF REACTIVITIES OF POLYMER-SUPPORTED FLUORIDE AND ACID FLUORIDES P+F-, NHF (N = 0-2) [J].
COUSSEAU, J ;
ALBERT, P .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5380-5383
[3]   ANHYDROUS TETRABUTYLAMMONIUM FLUORIDE - A MILD BUT HIGHLY EFFICIENT SOURCE OF NUCLEOPHILIC FLUORIDE-ION [J].
COX, DP ;
TERPINSKI, J ;
LAWRYNOWICZ, W .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3216-3219
[4]   ET3N.2HF, A NEW CONVENIENT REAGENT FOR NUCLEOPHILIC FLUORINE DISPLACEMENT-REACTIONS [J].
GIUDICELLI, MB ;
PICQ, D ;
VEYRON, B .
TETRAHEDRON LETTERS, 1990, 31 (45) :6527-6530
[5]  
LANDINI D, 1988, SYNTHESIS-STUTTGART, P953
[6]   DRAMATIC EFFECT OF THE SPECIFIC SOLVATION ON THE REACTIVITY OF QUATERNARY AMMONIUM FLUORIDES AND POLY(HYDROGEN FLUORIDES), (HF)-NORMAL.F-, IN MEDIA OF LOW POLARITY [J].
LANDINI, D ;
MAIA, A ;
RAMPOLDI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) :328-332
[8]   HIGH RESOLUTION NUCLEAR MAGNETIC RESONANCE SPECTRA OF BIFLUORIDE ION AND ITS HOMOLOGUES [J].
MARTIN, JS ;
FUJIWARA, FY .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (18) :3071-&
[9]   FACILE PREPARATION OF TETRABUTYLPHOSPHONIUM FLUORIDE AND ITS HF ADDUCTS - NEW FLUORIDE ANION SOURCES FOR SELECTIVE NUCLEOPHILIC FLUORINATION [J].
SETO, H ;
QIAN, Z ;
YOSHIOKA, H ;
UCHIBORI, Y ;
UMENO, M .
CHEMISTRY LETTERS, 1991, (07) :1185-1188
[10]   INSTABILITY OF ANHYDROUS TETRA-NORMAL-ALKYLAMMONIUM FLUORIDES [J].
SHARMA, RK ;
FRY, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (12) :2112-2114