A convenient route to beta,gamma-unsaturated esters without formation of the alpha,beta-isomers. Palladium-catalyzed alkoxycarbonylation of allylic halides under alcohol-potassium carbonate tow-phase conditions

被引：21

作者：

Kiji, J

Okano, T

Higashimae, Y

Fukui, Y

机构：

[1] Department of Materials Science, Faculty of Engineering, Tottori University

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1996年 / 69卷 / 04期

关键词：

D O I：

10.1246/bcsj.69.1029

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium-catalyzed, atmospheric pressure carbonylation of allylic halides under alcohol-potassium carbonate (liquid-solid) two-phase conditions affords beta,gamma-unsaturated esters without formation of the alpha,beta-isomers. Phosphine-free palladium compounds such as Pd(OAc)(2) (1) and Na-2[PdCl4] (2) are a convenient catalyst for this reaction. Presence of triphenylphosphine retards the carbonylation. A mixture of Pd(OAc)(2)-PPh(3) or [PdCl2(PPh(3))(2)] (3) catalyzes the carbonylation under pressure.

引用

页码：1029 / 1031

页数：3

共 17 条

[1] EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE
AMATORE, C
JUTAND, A
MBARKI, MA
[J]. ORGANOMETALLICS, 1992, 11 (09) : 3009 - 3013
[2] SYNTHESIS OF LACTONES BY THE PALLADIUM-CATALYZED CARBONYLATION OF HALO ALCOHOLS
COWELL, A
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (12) : 4193 - 4198
[3] CARBONYLATION OF ALLYLIC CHLORIDES
DENT, WT
WHITFIELD, GH
LONG, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1964, (MAY): : 1588 - &
[4] WATER-SOLUBLE LIGANDS, METAL-COMPLEXES, AND CATALYSTS - SYNERGISM OF HOMOGENEOUS AND HETEROGENEOUS CATALYSIS
HERRMANN, WA
KOHLPAINTNER, CW
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (11): : 1524 - 1544
[5] JENKINS JM, 1968, INORG SYNTH, V11, P108
[6] KIJI J, 1994, REV HETEROATOM CHEM, V11, P191
[7] PALLADIUM-CATALYZED, ATMOSPHERIC-PRESSURE CARBONYLATION OF ALLYLIC CHLORIDES IN 2-PHASE AQUEOUS SODIUM HYDROXIDE-ORGANIC SOLVENT MEDIA
KIJI, J
OKANO, T
NISHIUMI, W
KONISHI, H
[J]. CHEMISTRY LETTERS, 1988, (06) : 957 - 960
[8] PALLADIUM-CATALYZED, ATMOSPHERIC-PRESSURE ETHOXYCARBONYLATION OF ALLYLIC HALIDES UNDER THE INFLUENCE OF SODIUM ETHOXIDE - A FACILE SYNTHESIS OF BETA,GAMMA-UNSATURATED ESTERS
KIJI, J
OKANO, T
KONISHI, H
NISHIUMI, W
[J]. CHEMISTRY LETTERS, 1989, (10) : 1873 - 1876
[9] KIJI J, 1994, J SYNTH ORG CHEM JPN, V52, P276
[10] KUNTZ EG, 1987, CHEMTECH, V17, P570

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