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化学进展  2013 

可逆Diels-Alder反应

DOI: 10.7536/PC120949, PP. 999-1011

Keywords: 可逆D-A反应,呋喃/MI,智能材料,生物大分子,表面修饰

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Abstract:

通过高效的反应精确合成功能分子已成为现代化学发展的趋势之一。基于呋喃/马来酰亚胺(MI)之间的Diels-Alder(D-A)反应作为一种高效的和高选择性的点击反应,克服了铜催化的叠氮/炔之间的1,3-偶极环化加成(CuAAC)反应中引起的金属污染等缺点,为生物医药载体、功能性材料的制备提供更可行的途径。同时,呋喃/MI之间的D-A反应具备原料易得、反应条件温和及易发生retroD-A(rD-A)反应等优点,在制备响应性材料领域备受关注。本文综述了近年基于呋喃/MI的可逆D-A反应在响应性聚合物合成、智能材料、生物分子及表面修饰等方面的应用,并展望了D-A反应的发展前景。

References

[1]  Taylor M T, Blackman M L, Dmitrenko O, Fox J M. J. Am. Chem. Soc., 2011, 133: 9646-9649
[2]  Li Z B, Cai H C, Hassink M, Blackman M L, Brown R C D, Conti P S, Fox J M. Chem. Commun., 2010, 8043-8045
[3]  Gacal B, Durmaz H, Tasdelen M A, Hizal G, Tunca U, Yagci Y, Demirel A L. Macromolecules, 2006, 39: 5330-5336
[4]  熊兴泉 (Xiong X Q). 有机化学 (Chinese Journal of Organic Chemistry), 2010, 30: 307-310
[5]  Xiong X Q, Xu Y H. Polym. Bull., 2010, 65: 455-463
[6]  Xiong X Q, Chen Y M. Eur. Polym. J., 2012, 48: 569-579
[7]  Robertson A, Philp D, Spencer N, Tetrahedron, 1999, 55: 11365-11384
[8]  McElhanon J R, Wheeler D R. Org. Lett., 2001, 3: 2681-2683
[9]  Chujo Y, Sada K, Saegusa T. Macromolecules, 1990, 23: 2636-2641
[10]  Franc G, Kakkar A K. Chem. Eur. J., 2009, 15: 5630-5639
[11]  Grigoras M, Sava M, Colotin G, Simionescu C I. J. Appl. Polym. Sci., 2008, 107: 846-853
[12]  Kamahori K, Tada S, Ito K, Itsuno S. Macromolecules, 1999, 32: 541-547
[13]  Gandini A, Silvestre A J D, Coelho D. J. Polym. Sci., Part A: Polym. Chem., 2010, 48: 2053-2056
[14]  Vilela C, Cruciani L, Silvestre A J D, Gandini A. Macromol. Rapid. Commun., 2011, 32: 1319-1323
[15]  Aumsuwan N, Urban M W. Polymer, 2009, 50: 33-36
[16]  Gok O, Durmaz H, Ozdes1 E S, Hizal G, Tunca U, Sanyal A. J. Polym. Sci., Part A: Polym. Chem., 2010, 48: 2546-2556
[17]  Liu Y L, Chen Y W. Macromol. Chem. Phys., 2007, 208: 224-232
[18]  Peterson A M, Jensen R E, Palmese G R. ACS Appl. Mater. Interfaces, 2010, 2: 1141-1149
[19]  Zhang Y C, Broekhuis A A, Picchioni F. Macromolecules, 2009, 42: 1906-1912
[20]  Yoshie N, Watanabe M, Araki H, Ishida K. Polym. Degrad. Stab., 2010, 95: 826-829
[21]  Park J S, Darlington T, Starr A F, Takahashi K, Riendeau J, Hahn H T. Compos. Sci. Technol., 2010, 70: 2154-2159
[22]  Weizman H, Nielsen C, Weizman O S, Nemat-Nasser S. J. Chem. Educ., 2011, 88: 1137-1140
[23]  Magana S, Zerroukhi A, Jegat C, Mignard N. React. Funct. Polym., 2010, 70: 442-448
[24]  Imbesi P M, Fidge C, Raymond J E, Cau?t S, Wooley L. ACS Macro Lett., 2012, 1: 473-477
[25]  Adzima B J, Aguirre H A, Kloxin C J, Scott T F, Bowman C N. Macromolecules, 2008, 41: 9112-9117
[26]  Wei H L, Yang Z, Zheng L W, Shen Y M. Polymer, 2009, 50: 2836-2840
[27]  魏宏亮 (Wei H L), 杨哲 (Yang Z), 楚晖娟 (Chu H J), 朱靖 (Zhu J), 李志成 (Li Z C). 高分子通报 (Chin. Polym. Bull. ), 2010, 5: 50-54
[28]  Wei H L, Yang Z, Chen Y, Chu H J, Zhu J, Li Z C. Eur. Polym. J., 2010, 46: 1032-1039
[29]  Wei H L, Yang Z, Chen Y, Chu H J, Zhu J, Li Z C, Cui J S. Polymer, 2010, 51: 1694-1702
[30]  Zhang J J, Niu Y, Huang C L, Xiao L P, Chen Z T, Yang K K, Wang Y Z. Polym. Chem., 2012, 3: 1390-1393
[31]  Shi M, Wosnick J H, Ho K, Keating A, Shoichet M S. Angew. Chem. Int. Ed., 2007, 46: 6126-6131
[32]  Diels O, Alder K. Justus Liebigs Ann. Chem., 1928, 460: 98-122
[33]  Moses J, Moorhouse A. Chem. Soc. Rev., 2007, 36: 1249-1262
[34]  Kolb H C, Sharpless K B. Drug Discovery Today, 2003, 8: 1128-1137
[35]  Torn?e C W, Christensen C, Meldal M. J. Org. Chem., 2002, 67: 3057-3064
[36]  Rostovtsev V V, Green L G, Fokin V V, Sharpless K B. Angew. Chem. Int. Ed., 2002, 41: 2596-2599
[37]  Morten M, Christian W T. Chem. Rev., 2008, 108: 2952-3015
[38]  Wang Q, Hawker C. Chem. Asian J., 2011, 6: 2568-2569
[39]  熊兴泉 (Xiong X Q), 蔡雷 (Cai L), 唐忠科 (Tang Z K). 有机化学 (Chinese Journal of Organic Chemistry), 2012, 32: 1410-1428
[40]  Wang Q, Chan T R, Hilgraf R, Fokin V V, Sharpless K B, Finn M G. J. Am. Chem. Soc., 2003, 125: 3192-3193
[41]  Gierlich J, Burley G A, Gramlich P M E, Hammond D M, Carell T. Org. Lett., 2006, 8: 3639-3642
[42]  Lutz J F. Angew. Chem. Int. Ed., 2008, 47: 2182-2184
[43]  Qin A J, Tang L, Lam J W Y. Adv. Funct. Mater., 2009, 19: 1891-1900
[44]  Lallana E, Fernandez M E, Riguera, R. J. Am. Chem. Soc., 2009, 131: 5748-5750
[45]  Jim C K W, Qin A, Lam J W Y. Adv. Funct. Mater., 2010, 20: 1319-1328
[46]  Tasdelen M A. Polym. Chem., 2011, 2: 2133-2145
[47]  Hizal G, Tunca U, Sanyal A. J. Polym. Sci., Part A: Polym. Chem., 2011, 49: 4103-4120
[48]  Karver M R, Weissleder R, Hilderbrand S A. Bioconjugate Chem., 2011, 22: 2263-2270
[49]  Inglis A J, Sinnwell S, Stenzel M H, Barner-Kowollik C. Angew. Chem. Int. Ed., 2009, 48: 2411-2414
[50]  Durmaz H, Colakoclu B, Tunca U, Hizal G. J. Polym. Sci. Part A: Polym. Chem., 2006, 44: 1667-1675
[51]  Xiong X Q. Aust. J. Chem., 2009, 62: 1371-1377
[52]  Ripoll J L, Rouessac A, Rouessac F, Tetrahedron, 1978, 34: 19-40
[53]  Szalai M L, McGrath D V, Wheeler D R, Zifer T, McElhanon J R. Macromolecules, 2007, 40: 818-823
[54]  Kose M M, Yesilbag G, Sanyal A. Org. Lett., 2008, 10: 2353-2356
[55]  Goussé C, Gandini A, Hodge P. Macromolecules, 1998, 31: 314-421
[56]  Gheneim R, Berumen C P, Gandini A. Macromolecules, 2002, 35: 7246-7253
[57]  Palomo J M. Eur. J. Org. Chem., 2010, 6303-6314
[58]  Sanyal A. Macromol. Chem. Phys., 2010, 211: 1417-1425
[59]  Gandini A, Coelho D, Gomes M, Reis B, Silvestre A. J. Mater. Chem., 2009, 19: 8656-8664
[60]  Goussé C, Gandini A. Polym. Inter., 1999, 48: 723-731
[61]  Chou C I, Liu Y L. J. Polym. Sci. Part A: Poly. Chem., 2008, 46: 6509-6517
[62]  Gandini A, Silvestre A J D, Coelho D. Poly. Chem., 2011, 2: 1713-1719
[63]  Teramoto N, Arai Y, Shibata M. Carbohydr. Polym., 2006, 64: 78-84
[64]  Teramoto N, Niwa M, Shibata M. Materials, 2010, 3: 369-385
[65]  Jiang X B, Zhu W, Yan Y C, Chen Y M, Xi F. React. Funct. Polym., 2011, 71: 843-848
[66]  Tian Q, Yuan Y C, Rong M Z, Zhang M Q. J. Mater. Chem., 2009, 19: 1289-1296
[67]  Wei H L, Yang J, Chu H J, Yang Z, Ma C C, Yao K. J. Appl. Polym. Sci., 2011, 120: 974-980
[68]  Wei H L, Yao K, Yang Z, Chu H J, Zhu J, Ma C C, Zhao Z X. Macromol. Res., 2011, 19: 294-299
[69]  Nimmo C M, Owen S C, Shoichet M S. Biomacromolecules, 2011, 12: 824-830
[70]  Kavitha A A, Singha N K. Macromolecules, 2010, 43: 3193-3205
[71]  Deze T, Riva R, Raquez J M, Dubois P, Jerome C, Alexandre M. Macromol. Rapid. Commun., 2011, 32: 1264-1269
[72]  Raquez J M, Vanderstappen S, Meyer F, Verge P, Alexandre M, Thomassin J M, Jérme C, Dubois P. Chem. Eur. J., 2011, 17: 10135-10143
[73]  Toncelli C, Reus D C D, Picchioni F, Broekhuis A A. Macromol. Chem. Phys., 2012, 213: 157-165
[74]  Tona R, H?ner R. Bioconjugate Chem., 2005, 16: 837-842
[75]  Hill K W, Taunton-Rigby J, Carter J D, Kropp E, Vagle K. J. Org. Chem., 2001, 66: 5352-5358
[76]  Chen Y X, Triola G, Waldmann H. Acc. Chem. Res., 2011, 44: 762-773
[77]  Steven V, Graham D. Org. Biomol. Chem., 2008, 6: 3781-3787
[78]  Marchan V, Ortega S, Pulido D, Pedroso E, Grandas A. Nucleic Acids Res., 2006, 34: art. no. e24
[79]  Lu K, Duan Q P, Ma L, Zhao D X. Bioconjugate Chem., 2010, 21: 187-202
[80]  El-Sagheer A H, Cheong V V, Brown T. Org. Biomol. Chem., 2011, 9: 232-235
[81]  Zhu J, Kell A J, Workentin M S. Org. Lett., 2006, 8: 4993-4996
[82]  Costanzo P J, Beyer F L. Macromolecules, 2007, 40: 3996-4001
[83]  Bakhtiari A B S, Hsiao D, Jin G X, Gates B D, Branda N R. Angew. Chem. Int. Ed., 2009, 48: 4166-4169

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