Polymer/carrier composites as materials and reactors for organic synthesis

被引:41
作者
Kunz, U
Schönfeld, H
Kirschning, A
Solodenko, W
机构
[1] Tech Univ Clausthal, Inst Chem Verfahrenstech, D-38678 Clausthal Zellerfeld, Germany
[2] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
关键词
catalysts; monolithic polymer/carrier microreactor; polymer-supported reagents; Horner-Emmons olefination; Suzuki cross-coupling reaction;
D O I
10.1016/S0021-9673(03)00556-9
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
In this work new polymer/carrier composites are described which serve as novel materials in flow-through reactors for polymer-supported organic solution-phase synthesis. Monolithic polymer/carrier columns are prepared by a new precipitation polymerization process inside the void pore volume of megaporous glass carrier materials. Chemical functionalization of the internal polymer phase with chlorosulfonic acid or trimethylamine generates small, interconnected ion-exchange resin beads with a diameter of 1-3 mum which can be used for a large variety of organic syntheses. These monolithic rods are incorporated into an appropriate casing and can conveniently be operated in the flow-through mode. Important successful applications are polymer-assisted solution-phase reductions, oxidations and Homer-Emmons olefinations. Additionally, the use of these monolithic columns as catalytic microreactors and their performance in selected reactions are described. (C) 2003 Elsevier B.V. All rights reserved.
引用
收藏
页码:241 / 249
页数:9
相关论文
共 25 条
[1]   Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides [J].
Annis, DA ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4147-4154
[2]   Horner-Emmons synthesis with minimal purification using ROMPGEL: A novel high-loading matrix for supported reagents [J].
Barrett, AGM ;
Cramp, SM ;
Roberts, RS ;
Zecri, FJ .
ORGANIC LETTERS, 1999, 1 (04) :579-582
[3]   POLYMER-SUPPORTED PHOSPHONATES - OLEFINS FROM ALDEHYDES, KETONES, AND DIOXOLANS BY MEANS OF POLYMER-SUPPORTED PHOSPHONATES [J].
CAINELLI, G ;
CONTENTO, M ;
MANESCALCHI, F ;
REGNOLI, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (11) :2516-2519
[4]   Selected highlights in the application of ion-exchangers as supports for reagents in organic synthesis [J].
Chesney, A .
GREEN CHEMISTRY, 1999, 1 (05) :209-219
[5]  
Drewry DH, 1999, MED RES REV, V19, P97, DOI 10.1002/(SICI)1098-1128(199903)19:2<97::AID-MED2>3.0.CO
[6]  
2-Y
[7]   Practical access to highly enantioenriched C-3 building blocks via hydrolytic kinetic resolution [J].
Furrow, ME ;
Schaus, SE ;
Jacobsen, EN .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6776-6777
[8]   Asymmetric synthesis of 1-phenylpropanol using polymer-supported chiral catalysts in simple bench-top flow systems [J].
Hodge, P ;
Sung, DWL ;
Stratford, PW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (16) :2335-2342
[9]   Matrix assisted synthetic transformations: a mosaic of diverse contributions. I. The pattern emerges [J].
Hudson, D .
JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (05) :333-360
[10]   Combinatorial chemistry using polymer-supported reagents [J].
Kaldor, SW ;
Siegel, MG .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1997, 1 (01) :101-106