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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1437 - 1450

DOI: https://doi.org/10.6023/cjoc201212016

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Diels-Alder Cycloaddition Click Chemistry

  • Xiong Xingquan ,
  • Chen Huixin
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  • Key Laboratory for Functional Materials of Fujian Higher Education, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021

Received date: 2012-12-12

  Revised date: 2013-01-09

  Online published: 2013-01-11

Supported by

Project supported by the National Natural Science Foundation of China (No. 21004024), the Natural Science Foundation of Fujian Province (No. 2011J01046), the Program for New Century Excellent Talents in Fujian Province (No. 2012FJ-NCET-ZR03) and the University Distinguished Young Research Talent Training Program of Fujian Province (No. 11FJPY02).

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Abstract

Click reactions have rapidly become a new method for the synthesis of drugs, polymers and functional materials because of its high efficiency, high selectivity and reliable characteristics. With the further research of click reactions, the types of them are increasing continuously and the scope of application is also expanding at a fast rate. As an important reaction of click chemistry, Diels-Alder (D-A) reaction not only has high reaction efficiency, but also overcomes the shortcoming of using toxic heavy metal in the copper(I) catalyzed Cue-AAC reaction, so it provides a possible synthetic method for functional materials. Basing on the concept, characteristic and type of D-A reaction, this paper focuses upon the wide applications of D-A reaction in preparation of dendrimers, functional polymers and surface modification. Furthermore, the prospects of D-A reaction are also discussed.

Key words： Click chemistry; D-A reaction; functional polymers; surface modification; application

Cite this article

Xiong Xingquan , Chen Huixin . Diels-Alder Cycloaddition Click Chemistry[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1437 -1450 . DOI: 10.6023/cjoc201212016

References

[1] Kolb, H. C.; Finn, M. G.; Sharpless, B. K. Angew. Chem., Int. Ed. 2001, 40, 2004.
[2] Moses, J.; Moorhouse, A. Chem. Soc. Rev. 2007, 36, 1249.
[3] Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.
[4] Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
[5] Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
[6] Morten, M.; Christian, W. T. Chem. Rev. 2008, 108, 2952.
[7] Wang, Q.; Hawker, C. Chem. Asian J. 2011, 6, 2568.
[8] Xiong, X. Q.; Cai, L.; Tang, Z. K. Chin. J. Org. Chem. 2012, 32, 1410 (in Chinese). (熊兴泉, 蔡雷, 唐忠科, 有机化学, 2012, 32, 1410.)
[9] Wang, Q.; Chan, T. R.; Finn, G. J. Am. Chem. Soc. 2003, 125, 3192.
[10] Gierlich, J.; Burley, G. A.; Carell, T. Org. Lett. 2006, 8, 3639.
[11] Lutz, J. F. Angew. Chem., Int. Ed. 2008, 47, 2182.
[12] Qin, A. J.; Tang, L.; Lam, J. W. Y. Adv. Funct. Mater. 2009, 19, 1891.
[13] Lallana, E.; Fernandez, M. E.; Riguera, R. J. Am. Chem. Soc. 2009, 131, 5748.
[14] Jim, C. K. W.; Qin, A.; Lam, J. W. Y. Adv. Funct. Mater. 2010, 20, 1319.
[15] Tasdelen, M. A. Polym. Chem. 2011, 2, 2133.
[16] Palomo, J. M. Eur. J. Org. Chem. 2010, 6303.
[17] Hizal, G.; Tunca, U.; Sanyal, A. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 4103.
[18] Franc, G.; Kakkar, A. K. Chem. Eur. J. 2009, 15, 5630.
[19] Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. 1980, 19, 779.
[20] Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed., 2002, 41, 1668.
[21] Seelig, B.; Keiper, S.; Stuhlmann, F.; Jäschke, A. Angew. Chem., Int. Ed. 2000, 39, 4576.
[22] Durmaz, H.; Dag, A.; Cerit, N.; Sirkecioglu, O.; Hizal, G.; Tunca, U. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5982.
[23] Sanyal, A. Macromol. Chem. Phys. 2010, 211, 1417.
[24] Ripoll, J. L.; Rouessac A.; Rouessac, F. Tetrahedron 1978, 34, 19.
[25] Szalai, M. L.; McGrath, D. V. D.; Wheeler, R.; Zifer, T.; McElhanon, J. R. Macromolecules 2007, 40, 818.
[26] Robertson, A.; Philp, D.; Spencer, N. Tetrahedron 1999, 55, 11365.
[27] Haim, W.; Christian, N. J. Chem. Educ. 2011, 88, 1137.
[28] Chujo, Y.; Sada, K.; Saegusa, T. Macromolecules 1990, 23, 2636.
[29] Inglis, A. J.; Sinnwell, S.; Stenzel, M. H.; Barner-Kowollik, C. Angew. Chem., Int. Ed. 2009, 48, 2411.
[30] Taylor, M. T.; Blackman, M. L.; Dmitrenko, O.; Fox, J. M. J. Am. Chem. Soc. 2011, 133, 9646.
[31] Li, Z. B.; Cai, H. C.; Hassink, M.; Blackman, M. L.; Brown, R. C. D.; Conti, P. S.; Fox, J. M. Chem. Commun. 2010, 46, 8043.
[32] Karver, M. R.; Weissleder, R.; Hilderbrand, S. A. Bioconjugate Chem. 2011, 22, 2263.
[33] Adronov, A.; Fréchet, J. M. J. Chem. Commun. 2000, 114, 1701.
[34] Fant, K.; Esbjörner, E. K.; Lincoln, P.; Nordén, B. Biochemistry 2008, 47, 1732.
[35] Parrott, M. C.; Marchington, E. B.; Valliant, J. F.; Adronov, A. J. Am. Chem. Soc. 2005, 127, 12081.
[36] Parrott, M. C.; Benhabbour, S. R.; Saab, C.; Lemon, J. A.; Parker, S.; Valliant, J. F.; Adronov, A. J. Am. Chem. Soc. 2009, 131, 2906.
[37] Hawker, C.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 1990.
[38] Hawker, C.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1990, 15, 1010.
[39] Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C.; Scheel, A.; Voit, B.; Pyun, J.; Fréchet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928.
[40] Chen, G.; Kumar, J.; Gregory, A.; Stenzel, M. H. Chem. Commun. 2009, 41, 6291.
[41] Kose, M. M.; Onbulak, S.; Yilmaz, I. I.; Sanyal, A. Macromolecules 2011, 44, 2707.
[42] McElhanon, J. R.; Wheeler, D. R. Org. Lett. 2001, 3, 2681.
[43] Kose, M. M.; Yesilbag, G.; Sanyal, A. Org. Lett. 2008, 10, 2353.
[44] Vieyres, A.; Lam, T.; Gillet R.; Franc, G.; Castonguay, A.; Kakkar, A. Chem. Commun. 2010, 46, 1875.
[45] Xiong, X. Q. Aust. J. Chem. 2009, 62, 1371.
[46] Xiong, X. Q. Chin. J. Org. Chem. 2010, 30, 307 (in Chinese). (熊兴泉, 有机化学, 2010, 30, 307.)
[47] Tonga, M.; Cengiz, N.; Kose, M. M.; Dede, T.; Sanyal, A. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 410.
[48] Xiong, X. Q.; Chen, Y. M. Eur. Polym. J. 2012, 48, 569.
[49] Gandini, A.; Coelho, D.; Silvestre, A. J. D. Eur. Polym. J. 2008, 44, 4029.
[50] Gandini, A.; Silvestre, A. J. D.; Coelho, D. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 2053.
[51] Nebhani, L.; Sinnwell, S.; Lin, C. Y.; Coote, M. L.; Stenzel, M. H.; Barner-Kowollik, C. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 6053.
[52] Sinnwell, S.; Synatschke, C. V.; Junkers, T.; Stenzel, M. H.; Barner-Kowollik, C. Macromolecules 2008, 41, 7904.
[53] Sinnwell, S.; Inglis, A. J.; Davis, T. P.; Stenzel, M. H.; Barner-Kowollik, C. Chem. Commun. 2008, 2052.
[54] Hansell, C. F.; Espeel, P.; Stamenovic, M. M.; Barker, I. A.; Dove,A. P.; Prez, F. E. D.; O'Reilly, R. K. J. Am. Chem. Soc. 2011, 133, 13828.
[55] Durmaz, H.; Dag, A.; Altintas, O.; Erdogan, T.; Hizal, G.; Tunca, U. Macromolecules 2007, 40, 191.
[56] Glassner, M.; Oehlenschlaeger, K. K.; Gruendling, T.; Barner-Kowollik, C. Macromolecules 2011, 44, 4681.
[57] Winkler, M.; Mueller, J. O.; Oehlenschlaeger, K. K.; Espinosa, L. M. D.; Meier, M. A. R.; Barner-Kowollik, C. Macromolecules 2012, 45, 5012.
[58] Durmaz, H.; Hizal, G.; Tunca, U. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 1962.
[59] Mizawa, T.; Takenaka, K.; Shiomi, T. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 237.
[60] Durmaz, H.; Dag, A.; Hizal, G.; Tunca, U. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5083.
[61] Glassner, M.; Blinco, J. P.; Barner-Kowollik, C. Macromol. Rapid Commun. 2011, 32, 724.
[62] Xiong, X. Q.; Xu, Y. H. Polym. Bull. 2010, 65, 455.
[63] Durmaz, H.; Dag, A.; Gursoy, D.; Demirel, A. L.; Hizal, G.; Tunca, U. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 1557.
[64] Gunay, U. S.; Durmaz, H.; Gungor, E.; Dag, A.; Hizal, G.; Tunca, U. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 729.
[65] Pauloehrl, T.; Delaittre, G.; Winkler, V.; Welle, A.; Bruns, M.; Bçrner, H. G.; Greiner, A. M.; Bastmeyer, M.; Barner-Kowollik, C. Angew. Chem., Int. Ed. 2012, 51, 1071.
[66] Toombs-Ruane, H.; Pearson, E. L.; Paddon-Row, M. N.; Sherburn, M. S. Chem. Commun. 2012, 48, 6639.
[67] Rimmer, S.; Tattersall, P.; Ebdon, J. R.; Fullwood, N. React. Funct. Polym. 1999, 41, 177.
[68] Wei, H. L.; Yang, Z.; Chu, H. J.; Zhu, J.; Li, Z. C. Chin. Polym. Bull. 2010, 5, 50 (in Chinese). (魏宏亮, 杨哲, 楚晖娟, 朱靖, 李志成, 高分子通报, 2010, 5, 50.)
[69] Wei, H. L.; Yao, K.; Chu, H. J.; Li, Z. C.; Zhu. J.; Shen, Y. M.; Zhao, Z. X.; Feng, Y. L. J. Mater. Sci. 2012, 47, 332.
[70] Kim, C.; Kwark, K. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 4013.
[71] Defize, T.; Riva, R.; Jérôme, C.; Alexandre, M. Macromol. Chem. Phys. 2012, 213, 187.
[72] Nebhani, L.; Barner-Kowollik, C. Macromol. Rapid Commun. 2010, 31, 1298.
[73] Zydziak, N.; Hübner, C.; Bruns, M.; Barner-Kowollik, C. Macromolecules 2011, 44, 3374.
[74] Yuan, J. C.; Chen, G. H.; Weng, W. G.; Xu, Y. Z. J. Mater. Chem. 2012, 22, 7929.
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