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Progress in Chemistry 2010, Vol. 22 Issue (07): 1457-1470 Previous Articles   Next Articles

• Invited Article •

Soluble Polymer-Supported Homogeneous Catalysts

Liu  Ji1,2    Ma  Baode2    Yang  Nianfa1**    Fan  Jinghua2**   

  1. (1.Key Laboratory of Environmentally Friendly Chemistry, College of Chemistry, Xiangtan University, Xiangtan 411105, China; 2. CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, China.)
  • Received: Online: Published:
  • Contact: Fan Qinghua E-mail:fanqh@iccas.ac.cn
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Immobilization of a homogeneous catalyst can in principle facilitate its separation and recycling, and therefore is of considerable interest to both academia and industry. Soluble polymers, in particular dendrimers as an alternative catalyst supports have received increasing attention in recent years. This strategy allows a catalytic reaction to be carried out under homogeneous conditions. At the end of reaction, the immobilized catalyst could be easily separated and recycled through solvent precipitation and temperature-induced phase separation, or using membrane reactor. This paper reviews the progress in soluble polymer-supported catalysts, mainly including linear polymeric catalysts and dendrimeric catalysts which can be attached into polymeric support via covalent or noncovalent interactions, focusing on polymer-supported chiral catalysts and their use in asymmetric catalytic reactions.

Contents 
1 Introduction 
2 Types of soluble polymer-supported catalysts and methods for catalyst separation 
2.1 Main types of soluble polymer-supported catalysts 
2.2 Methods for catalyst separation 
3 Linear polymer-supported catalysts 
4 Dendrimer catalysts 
5 Noncovalent immobilization of catalysts with soluble supports 
6 Conclusion and outlook

Key words: linear polymers, dendrimers, homogeneous catalysis, asymmetric catalysis, immobilization

CLC Number: 

［1 ］ Noyori R. Asymmetric Catalysis in Organic Synthesis. New
York: Wiley，1994
［2 ］ Ojima I. Catalytic Asymmetric Synthesis. 2nd ed. New York:
Wiley，2000
［3 ］ Jacobsen E N， Pfaltz A， Yamamoto H. Comprehensive
Asymmetric Catalysis. Vol. 2. Berlin: Springer，1999
［4 ］ Lin G Q，Li Y M，Chan A S C. Principles and Applications of
Asymmetric Synthesis. New York: Wiley- Interscience，2001
［5 ］ Hawkins J M，Watson T J N. Angew. Chem. Int. Ed. ，2004，
43: 3224—3228
［6 ］ Cole-Hamilton D J. Science，2003，299: 1702—1706
［7 ］ 李月明( Li Y M) ，范青华( Fan Q H) ，陈新滋( Chan A S C) .
不对称有机反应———催化剂的回收与再利用( Asymmetric
Organic Reactions———Recycling and Reuse of Catalyst) . 北京:
化学工业出版社( Beijing: Chemical Industry Press) ，2003
［8 ］ de Vos D E，Vankelecom I F J，Jacobs P A，et al. Chiral
Catalyst Immobilization and Recycling. Weinheim: Wiley-VCH，
2000
［9 ］ Ding K L，Uozumi Y. Handbook of Asymmetric Heterogeneous
Catalysis. Weinheim: Wiley-VCH，2008
［10］ 丁奎岭(Ding K L) ，范青华( Fan Q H) . 手性催化剂负载化中
的若干新概念与新方法( Several Concepts and New Methods on
Chiral Catalyst Immobilization ) . 北京: 化学工业出版社
( Beijing: Chemical Industry Press) ，2008
［11］ Li C，Zhang H，Jiang D，et al. Chem. Commun. ，2007，547—
558
［12］ Yang Q，Han D，Yang H，et al. Chem. Asian. J. ，2009，3:
1214—1229
［13］ Ding K L，Wang Z，Wang X，et al. Chem. Eur. J. ，2006，12:
5188—5197
［14］ Wang Z，Chen G，Ding K L. Chem. Rev. ，2009，109: 322—
359
［15］ Ma L，Abney C，Lin W. Chem. Soc. Rev. ，2009，38: 1248—
1256
［16］ Astruc D，Chardac F. Chem. Rev. ，2001，101: 2991—3024
［17］ van Heerbeek R，Kamer P C J，van Leeuwen P W N M，et al.
Chem. Rev. ，2002，102: 3717—3756
［18］ Horvath I T，Rabai J. Science，1994，266: 72—75
［19］ 杨玉川(Yang Y C) ，魏莉(Wei L) ，金子林( Jin Z L) . 有机化
学(Organic Chemistry) ，2004，24: 579—584
［20］ Gladysz J A. Special Issue on Recoverable Catalysts and
Reagents. Chem. Rev. ，2002，102(10) : 3215—3892
［21］ Baker R T， Kobayashi S， Leitner W. Special Issue on
Multiphase， Green Solvent and Immobilization Strategies for
Molecular Catalysis. Adv. Synth. Catal. ，2006，348: 1337—
1340
［22］ Bergbreiter D E， Kobayashi S. Special Issue on Facilitated
Synthesis. Chem. Rev. ，2009，109(2) : 257—258
［23］ Dickerson T J，Need N N，Janda K D. Chem. Rev. ，2002，
102: 3325—3344
［24］ Bergbreiter D E. Chem. Rev. ，2002，102: 3345—3384
［25］ Bergbreiter D E，Tian J，Hongfa C. Chem. Rev. ，2009，109:
530—582
［26］ Fan Q H，Li Y M，Chan A S C. Chem. Rev. ，2002，102:
3385—3466
［27］ Oosterom G E，Reek J N H，Kamer P C J，et al. Angew.
Chem. Int. Ed. ，2001，40: 1828—1849
［28］ Gade L H. Top. Organomet. Chem. ，2006，20: 61—96
［29］ Fan Q H，Deng G J，Feng Y，et al. Enantioselective Catalysis
Using Dendrimer Supports ( in Handbook of Asymmetric
Heterogeneous Catalysis ( Eds. Ding K，Uozumi Y) . Weinheim:
Wiley-VCH，2008
［30］ Bergbreiter D E. Top. Curr. Chem. ，2004，242: 113—176
［31］ Van de Coevering R，Gebbink R J M K，van Koten G. Prog.
Polym. Sci. ，2005，30: 474—490
［32］ Dijkstra H P，van Klink G P M，van Koten G. ，Acc. Chem.
Res. ，2002，35: 798—810
［33］ Deng G J，Fan Q H，Chen X M，et al. Chem. Commun. ，
2002，1570—1571
［34］ Bergbreiter D E，Osburn P L，Smith T，et al. J. Am. Chem.
Soc. ，2003，125: 6245—6260
［35］ Han H，Janda K D. J. Am. Chem. Soc. ，1996，118: 7632—
7633
［36］ Guerreiro P， Ratovelomanana-Vidal V， Dellis P， et al.
Tetrahedron Lett. ，2001，42: 3423—3426
［37］ Li X G，Chen W P，Hems W，et al. Org. Lett. ，2003，5:
4559—4561
［38］ Zhao D B，Sun J，Ding K L. Chem. Eur. J. ，2004，10:
5952—5964
［39］ Hu X P，Huang J D，Zeng Q H，et al. Chem. Commun. ，
2006，293—295
［40］ Reed N N，Dickerson T J，Boldt G E，Janda K D. J. Org.
Chem. ，2005，70: 1728—1732
［41］ Hong S H，Grubbs R H. J. Am. Chem. Soc. ，2006，128:
3508—3509
［42］ Fan Q H， Deng G J， Chan A S C， et al. Tetrahedron:Asymmetry，2001，12: 1241—1248
［43］ Bergbreiter D E，Liu Y S，Osburn P L. J. Am. Chem. Soc. ，
1998，120: 4250—4251
［44］ Holbach M，Weck M. J. Org. Chem. ，2006，71: 1825—1836
［45］ Nakano T，Okamoto Y. Chem. Rev. ，2001，10: 4013—4038
［46］ Reggelin M，Schultz M，Holbach M. Angew. Chem. Int. Ed. ，
2002，41: 1614—1617
［47］ Yamamoto T，Suginome M. Angew. Chem. Int. Ed. ，2009，
48: 539—542
［48］ Huang W S，Anderson J，Pu L，et al. J. Am. Chem. Soc. ，
1997，119: 4313—4314
［49］ Pu L，Yu H B. Chem. Rev. ，2001，101: 757—824
［50］ Fan Q H，Hu W H，Chan A S C，et al. J. Am. Chem. Soc. ，
1999，121: 7407—7408
［51］ Newkome G R，Moorefield C N，Vgtle F. Dendrimers and
Dendrons， Concepts， Syntheses， Applications. Weinheim:
Wiley-VCH，2001
［52］ Fréchet J M J， Tomalia D. Dendrimers and Other Dendritic
Polymers. Chichester: Wiley-VCH，2001
［53］ Knapen J W J，van der Made A W，van Koten G，et al. Nature，
1994，372: 659—663
［54］ Helms B，Fréchet J M J. Adv. Synth. Catal. ，2006，348:
1125—1148
［55］ Breinbauer R，Jacobsen E N. Angew. Chem. Int. Ed. ，2000，
39: 3604—3607
［56］ Engel G D，Gade L H. Chem. Eur. J. ，2002，8: 4319—4329
［57］ Ribourdouille Y， Engel G D， Gade L H， et al. Chem.
Commun. ，2003，1228—1229
［58］ Kasssube J K，Wadepohl H，Gade L H. Adv. Synth. Catal. ，
2009，351: 607—616
［59］ Fan Q H，Chen Y M，Chan A S C，et al. Chem. Commun. ，
2000，789—790
［60］ Wang Z J，Deng G J，Fan Q H，et al. Org. Lett. ，2007，9:
1243—1246
［61］ Blaser H U，Pugin B，Togni A C R，Comptes Rendus Chimie，
2002，5: 379—385
［62］ Deng G J，Fan Q H，Chan A S C，et al. Chem. Commun. ，
2002，1570—1571
［63］ Zhang F，Fan Q H，Zhou Q L，et al. Chem. Commun. ，2008，
6048—6050
［64］ Chen Y C，Deng J G，Chan A S C，et al. Chem. Commun. ，
2001，1488—1489
［65］ Ji B M，Ding K L，Meng J B，et al. Chem. Eur. J. ，2003，9:
5989—5996
［66］ Wu Y Y，Zhao G，Wang S W，et al. Org. Lett. ，2006，8:
4417—4420
［67］ Breit B. Angew. Chem. Int. Ed. ，2005，44: 6816—6825
［68］ Kleij A W，Reek J N H. Chem. Eur. J. ，2006，12: 4218—
4227
［69］ Fraile J M，García J I，Mayoral J A. Chem. Rev. ，2009，109:
360—417
［70］ Michalek J H F，Tzschucke C C，Bannwarth W. Top. Curr.
Chem. ，2004，242: 43—75
［71］ Dai L X. Angew. Chem. Int. Ed. ，2004，43: 5726—5729
［72］ Beigbreiter D E，Case B，Liu Y S. Macromolecules，1998，31:
6035—6062
［73］ Schweb E，Mecking S. Organometallics，2001，20: 5504—5506
［74］ de Groot D，Reek J N H，Meijer E W，et al. J. Am. Chem.
Soc. ，2001，123: 8453—8458
［75］ Ooe M，Murata M，Kaneda K，et al. J. Am. Chem. Soc. ，
2004，126: 1604—1605
［76］ Li Y，He Y M，Fan Q H，et al. Org. Biomol. Chem. ，2009，
7: 1890—1895
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