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.

引用

页码：487 / 495

页数：9

共 50 条

[1] SHORT EFFECTIVE SYNTHESIS OF ALPHA-FLUOROKETONES BY PALLADIUM-CATALYZED DECARBOXYLATION REACTIONS OF ALLYL ALPHA-FLUORO-BETA-KETO CARBOXYLATES
SHIMIZU, I
ISHII, H
CHEMISTRY LETTERS, 1989, (04) : 577 - 580
[2] PALLADIUM-CATALYZED DECARBOXYLATION-DEHYDROGENATION OF ALLYL BETA-KETO CARBOXYLATES AND ALLYL ENOL CARBONATES AS A NOVEL SYNTHETIC METHOD FOR ALPHA-SUBSTITUTED ALPHA,BETA-UNSATURATED KETONES
SHIMIZU, I
TSUJI, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (21) : 5844 - 5846
[3] THE PALLADIUM-CATALYZED MICHAEL ADDITION-REACTION OF THE KETONE ENOLATES GENERATED BY THE DECARBOXYLATION OF ALLYL BETA-KETO CARBOXYLATES UNDER NEUTRAL CONDITIONS
NOKAMI, J
WATANABE, H
MANDAI, T
KAWADA, M
TSUJI, J
TETRAHEDRON LETTERS, 1989, 30 (36) : 4829 - 4832
[4] NEW SYNTHETIC REACTIONS OF ALLYL ALKYL CARBONATES, ALLYL BETA-KETO CARBOXYLATES, AND ALLYL VINYLIC CARBONATES CATALYZED BY PALLADIUM COMPLEXES
TSUJI, J
MINAMI, I
ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (04) : 140 - 145
[5] NEW PALLADIUM-CATALYZED SYNTHETIC REACTIONS OF ALLY BETA-KETO CARBOXYLATES AND FORMATE, AND THEIR APPLICATION TO NATURAL PRODUCT SYNTHESES
TSUJI, J
TAKAHASHI, T
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1987, 107 (02): : 87 - 106
[6] PREPARATION OF ALPHA-METHYLENE KETONES BY THE PALLADIUM-CATALYZED DECARBOXYLATION-DEACETOXYLATION OF ALLYL ALPHA-ACETOXYMETHYL-BETA-KETO CARBOXYLATES UNDER MILD CONDITIONS
TSUJI, J
NISAR, M
MINAMI, I
TETRAHEDRON LETTERS, 1986, 27 (22) : 2483 - 2486
[7] A NEW ONE-POT METHOD FOR ALPHA,ALPHA-DIALLYLATION OF KETONES BASED ON THE PALLADIUM-CATALYZED REACTION OF ALLYLIC CARBONATES AND ALLYL BETA-KETO CARBOXYLATES UNDER NEUTRAL CONDITIONS
SHIMIZU, I
OHASHI, Y
TSUJI, J
TETRAHEDRON LETTERS, 1983, 24 (36) : 3865 - 3868
[8] PALLADIUM-CATALYZED DECARBOXYLATION ALLYLATION OF ALLYLIC ESTERS OF ALPHA-SUBSTITUTED BETA-KETO CARBOXYLIC, MALONIC, CYANOACETIC, AND NITROACETIC ACIDS
TSUJI, J
YAMADA, T
MINAMI, I
YUHARA, M
NISAR, M
SHIMIZU, I
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14): : 2988 - 2995
[9] FACILE SYNTHESIS OF ALPHA-KETO ACIDS AND ESTERS BY PALLADIUM-CATALYZED DECARBOXYLATION REACTIONS OF DIALLYL ALPHA-OXALCARBOXYLATES
SHIMIZU, I
MAKUTA, T
OSHIMA, M
CHEMISTRY LETTERS, 1989, (08) : 1457 - 1460
[10] THE PALLADIUM-CATALYZED DIRECTED ALDOL REACTION OF ALDEHYDES WITH KETONE ENOLATES GENERATED BY THE DECARBOXYLATION OF ALLYL-BETA-KETO CARBOXYLATES UNDER NEUTRAL CONDITIONS
NOKAMI, J
MANDAI, T
WATANABE, H
OHYAMA, H
TSUJI, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) : 4126 - 4127

← 1 2 3 4 5 →