Reviews

Applications of Chitosan and Its Derivatives Supported Transitional Metal Catalysts in Organic Reactions

  • Wang Shuo ,
  • Zhou Hongyong ,
  • Song Shasha ,
  • Wang Jiaxi
Expand
  • School of Chemical Engineering, Hebei University of Technology, Tianjin 300130

Received date: 2014-06-16

  Revised date: 2014-07-18

  Online published: 2014-09-12

Supported by

Project supported by the Natural Science Foundation of Hebei Province (No. B2011202087).

Abstract

Due to its good coordination ability to the metal compounds, chitosan and its derivatives can be used as a kind of good catalysts carrier. Recently, the catalytic properties of chitosan and its derivatives supported metal catalyst have been attracted more attentions. Based on the kind of reactions, the applications of chitosan and its derivatives supported metal catalysts in the catalytic asymmetric reaction, allylic substitution, coupling, addition, oxidation, reduction and some other reactions are reviewed.

Cite this article

Wang Shuo , Zhou Hongyong , Song Shasha , Wang Jiaxi . Applications of Chitosan and Its Derivatives Supported Transitional Metal Catalysts in Organic Reactions[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 85 -91 . DOI: 10.6023/cjoc201406022

References

[1] Guibal, E.; Vincent, T.; Touraud, E.; Colombo, S.; Ferguson, A. J. Appl. Polym. Sci. 2006, 100, 3034.
[2] Kuehbeck. D.; Saidulu, G.; Redd, K. R.; Diaz, D. Green Chem. 2012, 14, 378.
[3] Reddy, K. R.; Rajgopal, K.; Maheswari, C. U.; Kantam, M. L. New J. Chem. 2006, 30, 1549.
[4] Zhang, J.-T.; Wei, G.; Keller, T. F.; Gallagher, H.; Stoetzel, C.; Mueller, F. A.; Gottschaldt, M.; Schubert, U. S.; Jandt, K. D. Macromol. Mater. Eng. 2010, 295, 1049.
[5] Primo, A.; Atienzar, P.; Sanchez, E.; Delgado, J. M.; Garcia, H. Chem. Commun. 2012, 48, 9254.
[6] El Kadib, A.; Bousmina, M. Chem-Eur. J. 2012, 18, 8264.
[7] Zeng, M.; Zhang, X.; Shao, L.; Qi, C.; Zhang, X.-M. J. Org. Chem. 2012, 704, 29.
[8] Zeng, M.; Zhang, X.; Qi, C.; Zhang, X.-M. Int. J. Biol. Macromol. 2012, 51, 730.
[9] Dhar, J.; Patil, S. ACS Appl. Mater. Inter. 2012, 4, 1803.
[10] Zhai, H.; Zhang, A.; Li, L.; Long, S. J. Appl. Polym. Sci. 2012, 123, 2140.
[11] Xiong, Y.; Wang, H.; Wu, C.; Wang, R. Polym. Adv. Technol. 2012, 23, 1429.
[12] Tsvetkova, I. B.; Bronstein, L. M.; Sidorov, S. N.; Lependina, O. L.; Sulman, M. G.; Valetsky, P. M.; Stein. B.; Nikoshvili, L. Z.; Matveeva, V. G.; Sidorov, A. I.; Tikhonov, B. B.; Demidenko, G. N.; Kiwi-Minsker, L.; Sulman, E. M. J. Mol. Catal. A: Chem. 2007, 276, 116.
[13] Yu, J.; Liu, T. In Eco-Materials Processing and Design X, Eds.: Kim, H.; Yang, J. F.; Sekino, T.; Lee, S. W., ISEPD, Xian, China, 2009, p. 537.
[14] Peirano, F.; Vincent, T.; Quignard, F.; Robitzer, M.; Guibal, E. J. Membr. Sci. 2009, 329, 30.
[15] Bradshaw, M.; Zou, J.; Byrne, L.; Iyer, K. S.; Stewart, S. G.; Raston, C. L. Chem. Commun. 2011, 47, 12292.
[16] Schiffman, J. D.; Schauer, C. L. Biomacromolecules 2007, 8, 2665.
[17] Chang, Y.-C.; Chen, D.-H. J. Colloid Interface Sci. 2005, 283, 446.
[18] Chang, Y.-C.; Chang, S.-W.; Chen, D.-H. React. Funct. Polym. 2006, 66, 335.
[19] Falco, M.; Retuert, J.; Hidrobo, A.; Covarrubias, C.; Araya, P.; Sedran, U. Appl. Catal. A 2009, 366, 269.
[20] Demetgül, C. Carbohydr. Polym. 2012, 89, 354.
[21] Zhao, Y.; Tian, H.-S.; Qi, X.-H.; Han, Z.-N.; Zhuang, Y.-Y.; He, L.-N. J. Mol. Catal. A: Chem. 2007, 271, 284.
[22] Sun, C.; Hu, B.; Zhao, D.; Liu, Z. J. Appl. Polym. Sci. 2012, 125, 79.
[23] Gong, S.-W.; He, H.-F.; Zhao, C.-Q.; Liu, L.-J.; Cui, Q.-X. Synth. Commun. 2012, 42, 574.
[24] Guibal, E. Prog. Polym. Sci. 2005, 30, 71.
[25] Macquarrie, D. J.; Hardy, J. J. E. Ind. Eng. Chem. Res. 2005, 44, 8499.
[26] Ricci, A.; Bernardi, L.; Gioia, C.; Vierucci, S.; Robitzer, M.; Quignard, F. Chem. Commun. 2010, 46, 6288.
[27] Cui, Y.-C.; Zhang, H.-F.; Li, R.-T.; Liu, Y.; Xu, C. Chin. J. Org. Chem. 2010, 30, 707 (in Chinese). (崔元臣, 张和凤, 李润涛, 刘毅, 许楚, 有机化学, 2010, 30, 707.)
[28] Babin, M.; Clement, R.; Gagnon, J.; Fontaine, F. G. New J. Chem. 2012, 36, 1548.
[29] Zhang, H.; Zhao, W.; Zou, J.; Liu, Y.; Li, R.; Cui, Y. Chirality 2009, 21, 492.
[30] Mac Leod, T. C. O.; Palaretti, V.; Barros, V. P.; Faria, A. L.; Silva, T. A.; Assis, M. D. Appl. Catal. A 2009, 361, 152.
[31] Qin, Y.; Zhao, W.; Yang, L.; Zhang, X.; Cui, Y. Chirality 2012, 24, 640.
[32] Zhang, H.-F.; Zhang. L.; Cui, Y.-C. React. Funct. Polym. 2007, 67, 322.
[33] Gioia, C.; Ricci, A.; Bernardi, L.; Bourahla, K.; Tanchoux, N.; Robitzer, M.; Quignard, F. Eur. J. Org. Chem. 2013, 3, 588.
[34] Giuseppe, A. D.; Crucianelli, M.; Passacantando, M.; Nisi, S.; Saladino, R. J. Catal. 2010, 276, 412.
[35] Baudoux, J.; Perrigaud, K.; Madec, P. J.; Gaumont, A. C.; Dez, I. Green Chem. 2007, 9, 1346.
[36] Moucel, R.; Perrigaud, K.; Goupil, J. M.; Madec, P. J.; Marinel, S.; Guibal, E.; Gaumont, A. C.; Dez, I. Adv. Synth. Catal. 2010, 352, 433.
[37] Zhang, Y.; Luo, S.; Zhu, C.-J. Chin. J. Org. Chem. 2012, 32, 2073 (in Chinese). (张艳, 罗莎, 朱成建, 有机化学, 2012, 32, 2073.)
[38] Yang, Y.; Li, G.; Song, Z.; Yang, X.; Liu, P. Lett. Org. Chem. 2010, 7, 533.
[39] Leonhardt, S. E. S.; Ondruschka, B.; Cravotto, G.; Leo, C. D.; Jandt, K. D.; Keller, T. F. Appl. Catal. A 2010, 379, 30.
[40] Xu, X.; Liu, P.; Li, S.-H.; Zhang, P.; Wang, X.-Y. React. Kinet. Catal. Lett. 2006, 88, 217.
[41] Gronnow, M. J.; Luque, R.; Macquarrie, D. J.; Clark, J. H. Green Chem. 2005, 7, 552.
[42] Cui, Y.-C.; Zhang, L.; Li, Y. Polym. Adv. Technol. 2005, 16, 633.
[43] Liu, P.; Liu, Y.; Li, J.-Y.; Liu, Y.-Z.; Lu, W.-P.; Wang, X.-Y.; Li, L.-M. Chin. J. Org. Chem. 2007, 27, 87 (in Chinese). (刘蒲, 刘晔, 李晶玉, 刘一真, 卢伟鹏, 王向宇, 李利民, 有机化学, 2007, 27, 87.)
[44] Chen, J.; Tang, J.-J.; Hu, C.-H.; Wang, J.-T. Chin. J. Inorg. Chem. 2009, 25, 147 (in Chinese). (陈静, 唐俊杰, 胡晨晖, 王锦堂, 无机化学学报, 2009, 25, 147.)
[45] Li, X.-W.; Zi, W.-W.; Guo, S.-W.; Xiao, D.-L.; Jian, G.-R. Polym. Adv. Technol. 2010, 21, 244.
[46] Cotugnoa, P.; Casielloa, M.; Naccia, A.; Mastrorillic, P.; Dell'Annac, M. M.; Monopolia, A. J. Organomet. Chem. 2014, 752, 1.
[47] Cravotto, G.; Garella, D.; Tagliapietra, S.; Stolle, A.; Schuessler, S.; Leonhardt, S. E. S.; Ondruschka, B. New J. Chem. 2012, 36, 1304.
[48] Lasri, J.; Mac Leod, T. C. O.; Pombeiro, A. J. L. Appl. Catal. A 2011, 397, 94.
[49] Sin, E.; Yi, S.-S.; Lee, Y.-S. J. Mol. Catal. A: Chem. 2010, 315, 99.
[50] Calo, V.; Nacci, A.; Monopoli, A.; Fornaro, A.; Sabbatini, L.; Cioffi, N.; Ditaranto, N. Organometallics 2004, 23, 5154.
[51] Primo, A.; Quignard, F. Chem. Commun. 2010, 46, 5593.
[52] Sophiphun, O.; Wittayakun, J.; Dhital, R. N.; Haesuwannakij, S.; Murugadoss, A.; Sakurai, H. Aust. J. Chem. 2012, 65, 1238.
[53] Alesi, S.; Di Maria, F.; Melucci, M.; Macquarrie, D. J.; Luque, R.; Barbarella, G. Green Chem. 2008, 10, 517.
[54] Corma, A.; Concepcion, P.; Dominguez, I.; Fornes, V.; Sabater, M. J. J. Catal. 2007, 251, 39.
[55] Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 114. 2708.
[56] Chtchigrovsky, M.; Primo, A.; Gonzalez, P.; Molvinger, K.; Robitzer, M.; Quignard, F.; Taran, F. Angew. Chem., Int. Ed. 2009, 48, 5916.
[57] Dekamin, M. G.; Azimoshan, M.; Ramezani, L. Green Chem. 2013, 15, 811.
[58] El Kadib, A.; Molvinger, K.; Bousmina, M.; Brunel, D. Org. Lett. 2010, 12, 948.
[59] Sudheesh, N.; Sharma, S. K.; Shukla, R. S. J. Mol. Catal. A: Chem. 2010, 321, 77.
[60] Kong, A.; Wang, P.; Zhang, H.; Yang, F.; Huang, S.; Shan, Y. Appl. Catal. A 2012, 417, 1839.
[61] Jose, T.; Sudheesh, N.; Shukla, R. S. J. Mol. Catal. A: Chem. 2010, 333, 158.
[62] Sun, C.; Hu, B.; Zhao, D.; Liu, Z. J. Appl. Polym. Sci. 2012, 125, 79.
[63] Guo, C.-C.; Huang, G.; Zhang, X.-B. Appl. Catal. A: Gen. 2003, 247, 261.
[64] Doggali, P.; Teraoka, Y.; Mungse, P.; Shah, I. K.; Rayalu, S.; Labhsetwar, N. J. Mol. Catal. A: Chem. 2012, 358, 23.
[65] Huang, G.; Guo, Y.-A.; Zhou, H.; Zhao, S.-K.; Liu, S.-Y.; Wang, A.-P.; Wei, J.-F. J. Mol. Catal. A: Chem. 2007, 273, 144.
[66] Huang, G.; Wang, A.-P.; Liu, S.-Y.; Guo, Y.-A.; Zhou, H.; Zhao, S.-K. Catal. Lett. 2007, 114, 174.
[67] Hall, S. R.; Collins, A. M.; Wood, N. J.; Ogasawara, W.; Morad, M.; Miedziak, P. J. RSC Adv. 2012, 2, 2217.
[68] Li, C.; Lei, Z.; Ma, H.; Wu, S.; Sun, Q. J. Dispersion Sci. Technol. 2012, 33, 983.
[69] Dabbawala, A. A.; Sudheesh, N.; Bajaj, H. C. Dalton. Trans. 2012, 41, 2910.
[70] Schüßler, S.; Blaubach, N.; Stolle, A.; Cravotto, G.; Ondruschka, B. Appl. Catal. A. 2012, 445, 231
[71] Wei, D.; Ye, Y.; Jia, X.; Yuan, C.; Qian, W. Carbohydr. Res. 2010, 345, 74.
[72] Chang, Y.-C.; Chen, D.-H. J. Hazard. Mater. 2009, 165, 664.
[73] Murugadoss, A.; Chattopadhyay, A. Nanotechnology 2008, 19, 1.
[74] Jia, X.-F.; Wang, Z.; Xia, C.-G.; Ding, K.-L. Chin. J. Org. Chem. 2013, 33, 1369 (in Chinese). (贾肖飞, 王正, 夏春谷, 丁奎岭, 有机化学, 2013, 33, 1369.)
[75] Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Green Chem. 2012, 14, 338.
[76] Tharun, J.; Hwang, Y.; Roshan, R.; Ahn, S.; Kathalikkattil, A. C.; Park, D.-W. Catal. Sci. Technol. 2012, 2, 1674.
[77] Sun, J.; Wang, J.; Cheng, W.; Zhang, J.; Li, X.; Zhang, S.; She, Y. Green Chem. 2012, 14, 654.
[78] Tharun, J.; Kim, D.-W.; Roshan, R.; Hwang, Y.; Park, D.-W. Catal. Commun. 2013, 31, 62.
[79] Gabriele, B.; Mancuso, R.; Salerno, G. Eur. J. Org. Chem. 2012, 6825.
[80] Liu, J.; Sun, W.; Zheng, S.; Xia, C. Helv. Chim. Acta 2007, 90, 1593.
[81] Xiang, Y.; Zhang, Q.; Si, J.; Du, J.; Guo, H.; Zhang, T. J. Mol. Catal. A: Chem. 2010, 322, 33.
[82] Chang, Y.-C.; Chen, D.-H. React. Funct. Polym. 2009, 69, 601.
[83] Chandrasekhar, V.; Athimoolam, A.; Srivatsan, S. G.; Sundaram, P. S.; Verma, S.; Steiner, A.; Zacchini, S.; Butcher, R. Inorg. Chem. 2002, 41, 5162.
[84] Srivatsan, S. G.; Verma, S. Chem.-Eur. J. 2001, 7, 828.

Outlines

/