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化学进展 2006, Vol. 18 Issue (0203): 316-329 前一篇   后一篇

• 综述与评论 •

树状大分子在有机合成中的应用*

赵立文1,2;范青华2**;周海峰1,2;何艳梅2;古练权1; 陈新滋3**   

  1. 1.中山大学化学与化学工程学院 中山大学药学院 广州 510275;2.中国科学院化学研究所 分子识别与选择性合成实验室 北京 100080;3.香港理工大学应用生物及化学系 香港
  • 收稿日期:2005-01-01 修回日期:2005-02-01 出版日期:2006-03-24 发布日期:2006-03-24
  • 通讯作者: 陈新滋
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Study of Dendrimers as Supports for Organic Synthesis

Liwen Zhao1,2;Qinghua Fan2**; Haifeng Zhou1,2; Yanmei He2; Lianquan Gu1; Albert S C Chan3**   

  1. 1.School of Chemistry and Chemical Engineering,School of Pharmaceutical Science, Sun Yat-Sen University,Guangzhou 510275,China;2.Laboratory of Molecular Recognition and Selective Synthesis, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China;3. Department of Applied Biology & Chemical  Technology, The Hong Kong Polytechnic University,Hong Kong, China
  • Received:2005-01-01 Revised:2005-02-01 Online:2006-03-24 Published:2006-03-24
  • Contact: Albert S C Chan
近20年来树状大分子由于其特殊的结构而引起了科学家们的广泛关注；作为一类新型的高负载量载体应用于有机合成和催化是树状大分子重要的应用领域之一。本文主要介绍树状大分子和树脂固载树状大分子两类载体，重点对它们作为高负载量载体在有机合成和非均相催化反应中的应用研究进行了总结。
关键词： 树状大分子载体, 有机合成, 催化, 负载
During recent 20 years, dendrimers have drawn great attention because of their unique highly branched structures. A promising application of dendrimers is that they can be used as high-loading supports for organic synthesis and catalysis. In this review, dendrimer supports and hybrids of these with solid-phase resins are described, focusing on the special features of high-loading dendritic architectures, applications in organic synthesis as well as catalysis.
Key words: dendrimer supports, organic synthesis, catalysis, immobilization

中图分类号: 

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[ 1 ] Buhleier E , Wehner W, Vêgtle F. Synthesis , 1978 , 155 —158
[ 2 ] Newkome G R , Yao Z Q , Baker G R , Gupta V K. J . Org.Chem. , 1985 , 50 : 2003 —2004
[ 3 ] Tomalia D A , Baker H , Dewald J R , Hall M, Kallos G, Martin S , Roeck J , Ryder J , Smith P. Polym. J . , 1985 , 17 : 117 —132
[ 4 ] Hawker C J , Frechet J M J . J . Am. Chem. Soc. , 1990 , 112 :7638 —7647
[ 5 ] Newkome G R , Moorefield C N , Vêgtle F. Dendrimers and Dendrons , Concepts , Syntheses and Applications. Weinheim:Wiley-VCH , 2002
[ 6 ] Vêgtle F , Gestermann S , Hesse R , Schwierz H , Windisch B.Prog. Polym. Sci . , 2000 , 25 : 987 —1041
[ 7 ] Dykes G M. J . Chem. Technol . Biotechnol . , 2001 , 76 : 903 —918
[ 8 ] Narayanan V V , Newkome G R. Top. Curr. Chem. , 1998 , 197 :19 —77
[ 9 ] Baars M W P L , Meijer E W. Top. Curr. Chem. , 2000 , 210 :131 —182
[10] Zimmerman S C , Lawless L J . Top. Curr. Chem. , 2001 , 217 :95 —120
[11] Boas U , Heegaard P M H. Chem. Soc. Rev. , 2004 , 33 : 43 —63
[12] Stiriba S E , Frey H , Haag R. Angew. Chem. Int . Ed. , 2002 ,41 : 1329 —1334
[13] Oosterom G E , Reek J N H , Kamer P C J , van Leeuwen P W N M. Angew. Chem. Int . Ed. , 2001 , 40 : 1828 —1849
[14] Astruc D , Chardac F. Chem. Rev. , 2001 , 101 : 2991 —3023
[15] Kreiter R , Kleij A W, Gebbink R J M K, van Koten G. Top.Curr. Chem. , 2001 , 217 : 163 —199
[16] Van Heerbeek R , Kamer P C J , van Leeuwen P W N M, Reek J N H. Chem. Rev. , 2002 , 102 : 3717 —3756
[17] Twyman L J , King A S H , Martin I K. Chem. Soc. Rev. , 2002 ,31 : 69 —82
[18] Hecht S , Fréchet J M J . Angew. Chem. Int . Ed. , 2001 , 40 : 74—91
[19] Fréchet J M J . J . Polym. Sci . Pol . Chem. , 2003 , 41 : 3713 —3725
[20] Merrifield R B. J . Am. Chem. Soc. , 1963 , 85 : 2149 —2154
[21] Kim R M, Manna M, Hutchins S M, Griffin P R , Yates N A ,Bernick A M, Chapman K T. Proc. Natl . Acad. Sci . USA ,1996 , 93 : 10012 —10017
[22] Hovestad N J , Ford A , Jastrzebski J T B H , van Koten G. J .Org. Chem. , 2000 , 65 : 6338 —6344
[23] Zhang J , Drugeon G, L′hermite N , Weston J . Tetrahedron Lett . ,2001 , 42 : 3599 —3601
[24] Zhang J , Aszodi J , Chartier C , L′hermite N , Weston J .Tetrahedron Lett . , 2001 , 42 : 6683 —6686
[25] Haag R. Chem. Eur. J . , 2001 , 7 : 327 —335
[26] Gebbink R J M K, Kruithof C A , van Klink G P M, van Koten G.Rev. Mol . Biotechnol . , 2002 , 90 : 183 —193
[27] Yates C R , Hayes W. Eur. Polym. J . , 2004 , 40 : 1257 —1281
[28] Gao C , Yan D. Prog. Polym. Sci . , 2004 , 29 : 183 —275
[29] Kantchev A B , Parquette J R. Tetrahedron Lett . , 1999 , 40 :8049 —8053
[30] Sunder A , Hanselmann R , Frey H , Mülhaupt R.Macromolecules , 1999 , 32 : 4240 —4246
[31] Sunder A , Mülhaupt R , Haag R , Frey H. Macromaolecules ,2000 , 33 : 253 —254
[32] Sunder A , Mülhaupt R , Haag R , Frey H. Adv. Mater. , 2000 ,12 : 235 —239
[33] Jayaraman M, Fréchet J M J . J . Am. Chem. Soc. , 1998 , 120 :12996 —12997
[34] Grayson S M, Jayaraman M, Fréchet J M J . Chem. Commun. ,1999 , 14 : 1329 —1330
[35] Haag R , Sunder A , StumbéJ F. J . Am. Chem. Soc. , 2000 ,122 : 2954 —2955
[36] Sunder A , Türk H , Haag R , Frey H. Macromolecules , 2000 ,33 : 7682 —7692
[37] Haag R , Sunder A , Hebel A , Roller S. J . Comb. Chem. ,2002 , 4 : 112 —119
[38] Hebel A , Haag R. J . Org. Chem. , 2002 , 67 : 9452 —9455
[39] Brown S D , Armstrong R W. J . Am. Chem. Soc. , 1996 , 118 :6331 —6332
[40] Hall D G, Tailer J , Gravel M. Angew. Chem. , 1999 , 111 :3250 —3253
[41] Roller S , Siegers C , Haag R. Tetrahedron , 2004 , 60 : 8711 —8720
[42] Jehle T, Feuerstein T J , Lagreze W A. Der Ophthalmologe ,2001 , 98 : 237 —241
[43] Freiman T M, Kukolja J , Heinemeyer J , Eckhardt K, Aranda H ,Rominger A , Dooley D J , Zentner J , Feuerstein T J . Naunyn Schmiedeberg’s Arch. Pharmacol . , 2001 , 363 : 537 —542
[44] Jehle T, Lagrèze W A , Blauth E , Knêrle R. Naunyn Schmiedeberg’s Arch. Pharmacol . , 2000 , 362 : 74 —81
[45] Potschka H , Feuerstein TJ , Loscher W. Naunyn-Schmiedeberg’s Arch. Pharmacol . , 2000 , 361 : 200 —205
[46] TamJ P. Proc. Natl . Acad. Sci . USA , 1988 , 85 : 5409 —5413
[47] Swali V , Wells N J , Langley J , Bradley M. J . Org. Chem. ,1997 , 62 : 4902 —4903
[48] Marsh I R , Smith H , Bradley M. Chem. Comm. , 1996 , 941 —942
[49] Basso A , Evans B , Pegg N , Bradley M. Tetrahedron Lett . ,2000 , 41 : 3763 —3767
[50] Basso A , Pegg N , Evans B , Bradley M. Eur. J . Org. Chem. ,2000 , 23 : 3887 —3891
[51] Basso A , Bradley M. Tetrahedron Lett . , 2003 , 44 : 2699 —2702
[52] Newkome G R , Weis C D , Childs B J . Des. Monom. Polym. ,1998 , 1 : 3 —14
[53] Fromont C , Bradley M. Chem. Comm. , 2000 , 283 —284
[54] Lebreton S , Newcombe N , Bradley M. Tetrahedron Lett . , 2002 ,43 : 2475 —2478
[55] Lebreton S , How S , Buchholz M, Yingyongnarongkul B , Bradley M. Tetrahedron , 2003 , 59 : 3945 —3953
[56] Lebreton S , Newcombe N , Bradley M. Tetrahedron , 2003 , 59 :10213 —10222
[57] Mahajan A , Chhabra S R , Chan W C. Tetrahedron Lett . , 1999 ,40 : 4909 —4912
[58] Basso A , Evans B , Pegg N , Bradley M. Chem. Commun. ,2001 , 697 —698
[59] Dahan A , Portnoy M. Macromolecules , 2003 , 36 : 1034 —1038
[60] Dahan A , Weissberg A , Portnoy M. Chem. Commun. , 2003 ,1206 —1207
[61] Dahan A , Dimant H , Portnoy M. J . Comb. Chem. , 2004 , 6 :305 —307
[62] Fan Q H , Li Y M, Chan A S C. Chem. Rev. , 2002 , 102 :3385 —3466
[63] Knapen J W J , van der Made A W, de Wilde J C , van Leeuwen P WM, Wijkens P , Grove DM, van Koten G. Nature , 1994 , 372 :659 —663
[64] Reetz M T, Lohmer G, Schwickardi R. Angew. Chem. Int . Ed. ,1997 , 36 : 1526 —1529
[65] Huang Y Y, Zhang H L , Deng G J , Tang W J , Wang X Y, He Y M, Fan Q H. J . Mol . Catal . A: Chem. , 2004 , 227 : 91 —96
[66] Tang W J , Yang N F , Yi B , Deng G J , Huang Y Y, Fan Q H.Chem. Commun. , 2004 , 1378 —1379
[67] Krishna T R , Jayaraman N. Tetrahedron , 2004 , 60 : 10325 —10334
[68] Francabvilla C , Bright J M J , Detty M R. Org. Lett . , 1999 , 1 :1043 —1046
[69] Bhyrappa P , Young J K, Moore J S , Suslick KS. J . Am. Chem.Soc. , 1996 , 118 : 5708 —5711
[70] Fan Q H , Chen Y M, Chen X M, Jiang D Z, Xi F , Chan A S C.Chem. Commun. , 2000 , 789 —790
[71] Deng G J , Fan Q H , Chen X M, Liu D S , Chan A S C. Chem.Commun. , 2002 , 1570 —1571
[72] Deng G J , Fan Q H , Chen X M, Liu G H. J . Mol . Catal . A:Chem. , 2003 , 193 : 21 —25
[73] Yi B , Fan Q H , Deng G, Li Y M, Qiu L Q , Chan A S C. Org Letter. , 2004 , 6 : 1361 —1364
[74] King A S H , Twyman L J . J . Chem. Soc. Perk. Tran. 1 , 2002 ,1 : 2209 —2218
[75] Tomalia D A , Baker H , Dewald J , Hall M, Kallos G, Martin S ,Roeck J , Ryder J , Smith P. Polym. J . , 1995 , 17 : 117 —132
[76] Bourque S C , Maltais F , Xiao W J , Tardif O , Alper H , Arya P ,Manzer L E. J . Am. Chem. Soc. , 1999 , 121 : 3035 —3038
[77] Bourque S C , Alper H. J . Am. Chem. Soc. , 2000 , 122 : 956 —957
[78] Reynhardt J P K, Yang Y, Sayari A , Alper H. Chem. Mater. ,2004 , 16 : 4095 —4102
[79] Duchateau R. Chem. Rev. , 2002 , 102 : 3525 —3542
[80] Arya P , Rao N V , Singkhonrat J , Alper H , Bourque S C , Manzer L E. J . Org. Chem. , 2000 , 65 : 1881 —1886
[81] Arya P , Panda G, Rao N V , Alper H , Bourque S C , Manzer L E. J . Am. Soc. Chem. , 2001 , 123 : 2889 —2890
[82] Lu S M, Alper H. J . Am. Chem. Soc. , 2003 , 125 : 13126 —13131
[83] Alper H , Arya P , Bourque S C , Jefferson G R , Manzer L E.Can. J . Chem. , 2000 , 78 : 920 —924
[84] Antebi S , Arya P , Manzer L E , Alper H. J . Org. Chem. , 2002 ,67 : 6623 —6631
[85] Reynhardt J P K, Alper H. J . Org. Chem. , 2003 , 68 : 8353 —8360
[86] Zweni P P , Alper H. Adv. Synth. Catal . , 2004 , 346 : 849 —854
[87] Lu S M, Alper H. J . Org. Chem. , 2004 , 69 : 3558 —3561
[88] Dahan A , Portnoy M. Org. Lett . , 2003 , 5 : 1197 —1200
[89] Dahan A , Portnoy M. Chem. Commun. 2002 , 2700 —2701
[90] Chung Y M, Rhee H K. Chem. Commun. , 2002 , 238 —239
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摘要

树状大分子在有机合成中的应用*