PALLADIUM-CATALYZED VINYLATION OF 4-BROMO-4'-HYDROXYBIPHENYL

被引:11
作者
KELKAR, AA [1 ]
HANAOKA, T [1 ]
KUBOTA, Y [1 ]
SUGI, Y [1 ]
机构
[1] NATL INST MAT & CHEM RES,TSUKUBA,IBARAKI 305,JAPAN
来源
JOURNAL OF MOLECULAR CATALYSIS | 1994年 / 88卷 / 02期
关键词
BASE EFFECTS; BIPHENYL; HECK REACTION; PALLADIUM CATALYST; PHOSPHINE LIGAND; VINYLATION;
D O I
10.1016/0304-5102(93)E0275-L
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Vinylation of 4-bromo-4'-hydroxybiphenyl and ethyl acrylate using Pd(OAc)2/PPh3 catalyst was studied. Ethyl 4-(4'-hydroxyphenyl) cinnamate was formed as the vinylation product, while, 4-hydroxybiphenyl and ethyl cinnamate were formed as side products. The results of the effects of phosphine structure and amount showed ethyl cinnamate was formed by the cleavage of the P-Ph bond of PPh3. Activity and selectivity of vinylation were highly improved with the use of inorganic bases and ethyl 4-(4'-hydroxyphenyl) cinnamate was formed in the yield over 99%.
引用
收藏
页码:L113 / L116
页数:4
相关论文
共 8 条
[1]   PALLADIUM-CATALYZED ARYLATION OF UNSYMMETRICAL OLEFINS - BIDENTATE PHOSPHINE LIGAND CONTROLLED REGIOSELECTIVITY [J].
CABRI, W ;
CANDIANI, I ;
BEDESCHI, A ;
SANTI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3558-3563
[2]  
CABRI W, 1991, J ORG CHEM, V56, P5797
[3]   PALLADIUM-CATALYZED VINYL SUBSTITUTION-REACTIONS .2. SYNTHESIS OF ARYL SUBSTITUTED ALLYLIC ALCOHOLS, ALDEHYDES, AND KETONES FROM ARYL HALIDES AND UNSATURATED ALCOHOLS [J].
CHALK, AJ ;
MAGENNIS, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07) :1206-1209
[4]  
CHALK AJ, 1980, CATALYSIS ORGANIC SY, P139
[5]   ORGANOPHOSPHINEPALLADIUM COMPLEXES AS CATALYSTS FOR VINYLIC HYDROGEN SUBSTITUTION-REACTIONS [J].
DIECK, HA ;
HECK, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1133-1136
[6]   COBALT ARYLPHOSPHINE HYDROFORMYLATION CATALYSTS - SUBSTITUENT EFFECTS ON THE STABILITY OF THE CARBON PHOSPHORUS BOND [J].
DUBOIS, RA ;
GARROU, PE .
ORGANOMETALLICS, 1986, 5 (03) :466-473
[7]  
HECK RF, 1982, ORG REACTIONS, V27, P345
[8]   PALLADIUM-CATALYZED REACTIONS OF ORGANIC HALIDES WITH OLEFINS [J].
HECK, RF .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (04) :146-151