SYNTHESIS OF ALPHA-FLUOROKETONES BASED ON PALLADIUM-CATALYZED DECARBOXYLATION REACTIONS OF ALLYL BETA-KETO CARBOXYLATES

被引：23
|
作者：
SHIMIZU, I
ISHII, H
机构：
[1] Department of Applied Chemisty, School of Science and Engineering, Waseda University, Tokyo, 169
来源：
TETRAHEDRON | 1994年 / 50卷 / 02期
关键词：
D O I：
10.1016/S0040-4020(01)80770-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Fluorination of allyl beta-keto carboxylates using N-fluoro-2,4,6-pyridinium triflate gave allyl a-fluoro-a-keto carboxylates. Reaction of allyl alpha-fluoro-beta-keto carboxylates with formic acid in the presence of palladium-phosphine catalyst gave alpha-fluoro ketones. When the palladium-catalyzed reaction was carried out without formic acid, the decarboxylation-allylation took place to give alpha-fluoro-allylketones. Decarboxylation-dehydrogenation to afford alpha-fluoro-alpha,beta-unsaturated ketones was carried out with palladium catalysts in acetonitrile.
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页码：487 / 495
页数：9
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