Hydroesterification of styrene catalyzed by montmorillonite-diphenylphosphinepalladium(II) chloride in the presence of chiral phosphines

被引:47
作者
Nozaki, K
Kantam, ML
Horiuchi, T
Takaya, H
机构
[1] Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-01, Sakyo-ku
基金
日本学术振兴会;
关键词
styrene; hydroesterification; chiral phosphines; montmorillonite; palladium complex; regioselectivity;
D O I
10.1016/S1381-1169(96)00385-8
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
The catalyst system, montmorillonite-diphenylphosphinepalladium(II) chloride complex, HCl-NMDPP, afforded the corresponding branched ester quantitatively at 125 degrees C and 45 atm of CO pressure. The high catalytic activity (substrate/Pd = 500) demonstrates its potential use on commercial scale although the enantioselectivity is not satisfactory. In contrast to previous studies, bulky bidentate ligands were also effective because of the higher interlamellar spacings of the catalyst.
引用
收藏
页码:247 / 253
页数:7
相关论文
共 38 条
[1]   ASYMMETRIC-SYNTHESIS OF ACIDS BY THE PALLADIUM-CATALYZED HYDROCARBOXYLATION OF OLEFINS IN THE PRESENCE OF (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL OR (S)-(+)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE [J].
ALPER, H ;
HAMEL, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2803-2804
[2]   THE REGIOSPECIFIC PALLADIUM CATALYZED HYDROCARBOXYLATION OF ALKENES UNDER MILD CONDITIONS [J].
ALPER, H ;
WOELL, JB ;
DESPEYROUX, B ;
SMITH, DJH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (21) :1270-1271
[3]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[4]   CARBONYLATION OF OLEFINS UNDER MILD TEMPERATURE CONDITIONS IN PRESENCE OF PALLADIUM COMPLEXES [J].
BITTLER, K ;
VONKUTEP.N ;
NEUBAUER, D ;
REIS, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (05) :329-&
[5]   Synthesis of gamma-ketocycloalkanecarboxylic acid esters by region-specific alkoxy carbonylation of alpha,beta-ketocycloolefins catalyzed by palladium [J].
Cavinato, G ;
Toniolo, L .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 104 (03) :221-227
[6]   ON THE MECHANISM OF THE HYDROCARBALKOXYLATION OF OLEFINS CATALYZED BY PALLADIUM COMPLEXES [J].
CAVINATO, G ;
TONIOLO, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 398 (1-2) :187-195
[7]   SYNTHESIS, REACTIONS AND CATALYTIC ACTIVITIES OF IRIDIUM COMPLEXES INTERCALATED INTO MONTMORILLONITE [J].
CHIN, CS ;
LEE, BG ;
YOO, IY ;
KWON, TH .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (04) :581-585
[8]   SYNTHESIS AND CATALYTIC ACTIVITY IN SELECTIVE HYDROGENATION OF PALLADIUM COMPLEXES ANCHORED IN MONTMORILLONITE [J].
CHOUDARY, BM ;
KUMAR, KR ;
KANTAM, ML .
JOURNAL OF CATALYSIS, 1991, 130 (01) :41-51
[9]   A HIGHLY SELECTIVE MONTMORILLONITE CATALYST FOR HYDROGENATION OF ALKYNES, ALKENYNES, AND ALKADIENES [J].
CHOUDARY, BM ;
VASANTHA, G ;
SHARMA, M ;
BHARATHI, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (04) :465-466
[10]   ASYMMETRIC INDUCTION IN CARBOMETHOXYLATION OF VINYLAROMATICS [J].
COMETTI, G ;
CHIUSOLI, GP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 236 (01) :C31-C32