Catalyst product separation techniques in Heck reaction

被引:171
作者
Bhanage, BM [1 ]
Arai, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Mat Sci & Engn, Sapporo, Hokkaido 0608628, Japan
来源
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING | 2001年 / 43卷 / 03期
关键词
Heck reaction; heterogeneous catalysis; homogeneous catalysis; separation; vinylation;
D O I
10.1081/CR-100107480
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 Heck reaction finds several applications in industry because it is one of the effective tools for the formation of a new C-C bond. In addition to the catalytic activity and selectivity, catalyst-product separation strategies are very important for the industrial application. There are various methods of interest ranging from conventional heterogeneous catalysts to heterogenization of homogeneous catalysts. The heterogeneous catalysts are classified into supported metal catalysts, zeolite-encapsulated catalysts, colloids-nanoparticles, and intercalated metal compounds. The homogeneous metal complexes catalysts are heterogenized using modified silica catalysts, polymer-supported catalysts. biphasic catalysts, supported liquid-phase catalysts, nonionic liquids solvents. perfluorinated solvents, and reusable homogeneous complexes. In general, heterogeneous catalysts are effective and stable at higher temperatures, which may be important for the activation of less reactive but less expensive chloroaryls substrates. However. the heterogeneous catalysts have a major drawback of poor selectivity toward Heck coupling products. The heterogenized metal complexes catalysts operate under relatively mild conditions as compared with heterogeneous catalysts, and so they can be applied to the production of pharmaceuticals and fine chemicals. Catalysis using supercritical solvents with catalyst separation techniques is promising for the development of green chemistry processes. Although the concepts described in this article have been reviewed mainly for Heck reactions, they should be applicable to a wide range of other chemical transformations (hydrogenation, carbonylation, hydroformylation, and so on) that, currently, are homogeneously catalyzed reactions.
引用
收藏
页码:315 / 344
页数:30
相关论文
共 83 条
[1]   Orthopalladated triarylphosphite complexes as highly efficient catalysts in the Heck reaction [J].
Albisson, DA ;
Bedford, RB ;
Scully, PN .
TETRAHEDRON LETTERS, 1998, 39 (52) :9793-9796
[2]   Heck reaction using palladium complexed to dendrimers on silica [J].
Alper, H ;
Arya, P ;
Bourque, SC ;
Jefferson, GR ;
Manzer, LE .
CANADIAN JOURNAL OF CHEMISTRY, 2000, 78 (06) :920-924
[3]   PALLADIUM PHOSPHINATED POLYSTYRENE AS A CATALYST IN THE HECK ARYLATION - A COMPARATIVE-STUDY [J].
ANDERSSON, CM ;
KARABELAS, K ;
HALLBERG, A ;
ANDERSSON, C .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3891-3895
[4]   SYNTHESIS OF BETA-ARYLVINYL ETHERS BY THE PALLADIUM-CATALYZED REACTION OF AROYL CHLORIDES WITH VINYL ETHERS [J].
ANDERSSON, CM ;
HALLBERG, A .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) :235-239
[5]   Palladium catalysed Heck and enantioselective allylic substitution reactions using reverse phase silica supports [J].
Anson, MS ;
Mirza, AR ;
Tonks, L ;
Williams, JMJ .
TETRAHEDRON LETTERS, 1999, 40 (39) :7147-7150
[6]   HYDROFORMYLATION BY SUPPORTED AQUEOUS-PHASE CATALYSIS - A NEW CLASS OF HETEROGENEOUS CATALYSTS [J].
ARHANCET, JP ;
DAVIS, ME ;
MEROLA, JS ;
HANSON, BE .
NATURE, 1989, 339 (6224) :454-455
[7]   HETEROGENEOUS CATALYSIS IN ORGANIC-CHEMISTRY .8. THE USE OF SUPPORTED PALLADIUM CATALYSTS FOR THE HECK ARYLATION [J].
AUGUSTINE, RL ;
OLEARY, ST .
JOURNAL OF MOLECULAR CATALYSIS, 1992, 72 (02) :229-242
[8]   HETEROGENEOUS CATALYSIS IN ORGANIC-CHEMISTRY .10. EFFECT OF THE CATALYST SUPPORT ON THE REGIOCHEMISTRY OF THE HECK ARYLATION REACTION [J].
AUGUSTINE, RL ;
OLEARY, ST .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 95 (03) :277-285
[9]  
BELLER M, 1995, SYNLETT, P441
[10]   First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems [J].
Beller, M ;
Fischer, H ;
Kuhlein, K ;
Reisinger, CP ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 520 (1-2) :257-259