Progress in Ring Opening Polymerization of Lactides Catalyzed by Chiral Organometallic Complexes

doi:10.6023/cjoc201612011

Abstract

Polylactides have received considerable attention in recent years due to their outstanding properties such as biocompatibility, biodegradability, and renewability. In particular, the studies on ring opening polymerization (ROP) of lactides in stereoselective manner catalyzed by chiral organometallic complexes have been regarded as one of the most significant fields in the synthesis of polylactides. The important advances in the ROP of lactides catalyzed by chiral organometallic complexes are reviewed in this article.

Key words: chiral organometallic complexes, catalysis, polymerization of lactides

Cite this article

Zhao Ning. Progress in Ring Opening Polymerization of Lactides Catalyzed by Chiral Organometallic Complexes[J]. Chin. J. Org. Chem., 2017, 37(5): 1139-1159.

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References

[1] (a) Chiellini, E.; Solaro, R. Adv. Mater. 1996, 8, 305.
(b) Uhrich, K. E.; Cannizzaro, S. M.; Langer, R. S.; Shakesheff, K. M. Chem. Rev. 1999, 99, 3181.
(c) Drumright, R. E.; Gruber, P. R.; Henton, D. E. Adv. Mater. 2000, 12, 1841.
(d) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467.
(e) Ghosh, S. J. Chem. Res. 2004, 241.
(f) Auras, R.; Harte, B.; Selke, S. Macromol. Biosci. 2004, 4, 835.
(g) Tsuji, H. Macromol. Biosci. 2005, 5, 569.
(h) Gunatillake, P.; Mayadunne, R.; Adhikari, R. Biotechnol. Ann. Rev. 2006, 12, 301.
(i) Wu, J.; Yu, T.-L.; Chen, C.-T.; Lin, C.-C. Coord. Chem. Rev. 2006, 250, 602.
(j) Amgoune, A.; Thomas, C. M.; Carpentier, J.-F. Pure Appl. Chem. 2007, 79, 2013.
(k) Dove, A. P. Chem. Commun. 2008, 6446.
(l) Wheaton, C. A.; Hayes, P. G.; Ireland, B. J. Dalton Trans. 2009, 4832.
(m) Stanford, M. J.; Dove, A. P. Chem. Soc. Rev. 2010, 39, 486.
[2] (a) Zhang, G.; Yang, J.; Feng, X. Prog. Chem. 2000, 12, 89 (in Chinese). (张国栋, 杨纪元, 冯新德, 化学进展, 2000, 12, 89.)
(b) Liu, F.; Cheng, W. Polym. Bull. 2004, 6, 38 (in Chinese). (刘凤兴, 程为庄, 高分子通报, 2004, 6, 38.)
(c) Cui, W.; Bei, J.; Wang, S. Polym. Bull. 2005, 5, 16 (in Chinese). (崔文瑾, 贝建中, 王身国, 高分子通报, 2005, 5, 16.)
(d) Bai, Y.; Huang, X.; Lei, Z. Polym. Bull. 2006, 3, 46 (in Chinese). (白雁斌, 黄晓琴, 雷自强, 高分子通报, 2006, 3, 46.)
[3] Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1316.
[4] (a) O'Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. J. Chem. Soc., Dalton Trans. 2001, 2215.
(b) Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147.
(c) Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813.
(d) Platel, R. H.; Hodgson, L. M.; Williams, C. K. Polym. Rev. 2008, 48, 11.
(e) Zhang, Z.; Zi, G. Chin. J. Org. Chem. 2009, 29, 1059 (in Chinese). (张站斌自国甫, 有机化学, 2009, 29, 1059.)
(f) Gu, L.; Zhu, G.; Song, H.; Zi, G. Chin. J. Org. Chem. 2009, 29, 1499 (in Chinese). (古丽娜, 祝冠彬, 宋海斌, 自国甫, 有机化学, 2009, 29, 1499.)
(g) Thomas, C. M. Chem. Soc. Rev. 2010, 39, 165.
(h) Sauer, A.; Kapelski, A.; Fliedel, C.; Dagorne, S.; Kol, M.; Okuda, J. Dalton Trans. 2013, 42, 9007.
(i) Zhang, D.; Zi, G. Chem. Soc. Rev. 2015, 44, 1898.
[5] Chisholm, M. H.; Eilerts, N. W.; Huffman, J. C.; Iyer, S. S.; Pacold, M.; Phomphrai, K. J. Am. Chem. Soc. 2000, 122, 11845.
[6] Labourdette, G.; Lee, D. J.; Patrick, B. O.; Ezhova, M. B.; Mehrkhodavandi, P. Organometallics 2009, 28, 1309.
[7] Drouin, F.; Oguadinma, P. O.; Whitehorne, T. J. J.; Prud'homme, R. E.; Schaper, F. Organometallics 2010, 29, 2139.
[8] Börner, J.; Flörke, U.; Döring, A.; Kuckling, D.; Jones, M. D.; Steiner, M.; Breuning, M.; Herres-Pawlis, S. Inorg. Chem. Commun. 2010, 13, 369.
[9] Darensbourg, D. J.; Karroonnirun, O. Inorg. Chem. 2010, 49, 2360.
[10] Pastor, M. F.; Whitehorne, T. J. J.; Oguadinma, P. O.; Schaper, F. Inorg. Chem. Commun. 2011, 14, 1737.
[11] Otero, A.; Fernández-Baeza, J.; Sánchez-Barba, L. F.; Tejeda, J.; Honrado, M.; Garcés, A.; Lara-Sánchez, A.; Rodríguez, A. M. Organometallics 2012, 31, 4191.
[12] (a) Zhang, Z.; Zhao, N.; Ren, W.; Chen, L.; Song, H.; Zi G. Inorg. Chem. Commun. 2012, 20, 234.
(b) Zhao, N.; Chen, L.; Ren, W.; Song, H.; Zi, G. J. Organomet. Chem. 2012, 712, 29.
[13] Honrado, M.; Otero, A.; Fernández-Baeza, J.; Sánchez-Barba, L. F.; Lara-Sánchez, A.; Tejeda, J.; Carrión, M. P.; Martínez-Ferrer, J.; Garcés, A.; Rodríguez, A. M. Organometallics 2013, 32, 3437.
[14] Wang, H.; Ma, H. Chem. Commun. 2013, 49, 8686.
[15] Honrado, M.; Otero, A.; Fernández-Baeza, J.; Sánchez-Barba, L. F.; Garcés, A.; Lara-Sańchez, A.; Rodríguez, A. M. Organometallics 2014, 33, 1859.
[16] Abbina, S.; Du, G. ACS Macro Lett. 2014, 3, 689.
[17] Gao, A.; Yao, W.; Xiao, Y.; Zhang, M.; Zhu, G.; Zhang, N.; Wang, S.; Wang, D.; Zhang, Y.; Gao, Y.; Xu, Z.; Lu, P.; Zhang, Z. Polyhedron 2015, 85, 537.
[18] Spassky, N.; Wisniewski, M.; Pluta, C.; Borgne, A. L. Macromol. Chem. Phys. 1996, 197, 2627.
[19] Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072.
[20] Zhong, Z.; Dijkstra, P. J.; Feijen, J. Angew. Chem., Int. Ed. 2002, 41, 4510.
[21] Zhong, Z.; Dijkstra, P. J.; Feijen, J. J. Am. Chem. Soc. 2003, 125, 11291.
[22] Bouyahyi, M.; Grunova, E.; Marquet, N.; Kirillov, E.; Thomas, C. M.; Roisnel, T.; Carpentier, J.-F. Organometallics 2008, 27, 5815.
[23] Du, H.; Velders, A. H.; Dijkstra, P. J.; Sun, J.; Zhong, Z.; Chen, X.; Feijen, J. Chem. Eur. J. 2009, 15, 9836.
[24] Castro-Osma, J. A.; Alonso-Moreno, C.; Már quez-Segovia, I.; Otero, A.; Lara-Sánchez, A.; Fernández-Baeza, J.; Rodríguez, A. M.; Sánchez-Barba, L. F.; García-Martínez, J. C. Dalton Trans. 2013, 42, 9325.
[25] Gao, B.; Duan, R.; Pang, X.; Li, X.; Qu, Z.; Tang, Z.; Zhuang, X.; Chen, X. Organometallics 2013, 32, 5435.
[26] (a) Zhao, N.; Wang, Q.; Hou, G.; Song, H.; Zi, G. J. Organomet. Chem. 2014, 754, 51.
(b) Zhao, N.; Wang, Q.; Hou, G.; Song, H.; Zi, G. Inorg. Chem. Commun. 2014, 41, 6.
[27] (a) Zhao, N.; Wang, Q.; Hou, G.; Song, H.; Zi, G. Inorg. Chim. Acta 2014, 413, 128.
(b) Zhao, N.; Wang, Q.; Hou, G.; Song, H.; Zi, G. Inorg. Chem. Commun. 2014, 44, 86.
[28] Pilone, A.; Press K.; Goldberg, I.; Kol, M.; Mazzeo, M.; Lamberti, M. J. Am. Chem. Soc. 2014, 136, 2940.
[29] Go, M. J.; Kim, S. H.; Kang, Y. Y.; Park, H.-R.; Kim, Y.; Lee, J. Inorg. Chem. Commun. 2014, 44, 139.
[30] Bian, S.; Abbina, S.; Lu, Z.; Kolodka, E.; Du, G. Organometallics 2014, 33, 2489.
[31] Gao, B.; Li, D.; Duan, Q.; Duan, R.; Pang, X. New J. Chem. 2015, 39, 4670.
[32] Chamberlain, B. M.; Sun, Y.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G.; Jr.; Pink, M.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400.
[33] Alaaeddine, A.; Amgoune, A.; Thomas, C. M.; Da gorne, S.; Bellemin-Laponnaz, S.; Carpentier, J.-F. Eur. J. Inorg. Chem. 2006, 3652.
[34] Heck, R.; Schulz, E.; Collin, J.; Carpentier, J.-F. J. Mol. Catal. A: Chem. 2007, 268, 163.
[35] Platel, R. H.; White, A. J. P.; Williams, C. K. Inorg. Chem. 2008, 47, 6840.
[36] Zi, G.; Wang, Q.; Xiang, L.; Song, H. Dalton Trans. 2008, 5930.
[37] Wang, Q.; Xiang, L.; Song, H.; Zi, G. J. Organomet. Chem. 2009, 694, 691.
[38] Otero, A.; Fernández-Baeza, J.; Lara-Sánchez, A.; Alonso-Moreno, C.; Márquez-Segovia, I.; Sánchez-Barba, L. F.; Rodríguez, A. M. Angew. Chem., Int. Ed. 2009, 48, 2176.
[39] Zhang, F.; Zhang, J.; Song, H.; Zi, G. Inorg. Chem. Commun. 2011, 14, 72.
[40] Kratsch, J.; Kuzdrowska, M.; Schmid, M.; Kazeminejad, N.; Kaub, C.; Oña-Burgos, P.; Guillaume, S. M.; Roesky, P. W. Organometallics 2013, 32, 1230.
[41] Ren, W.; Chen, L.; Zhao, N.; Wang, Q.; Hou, G.; Zi, G. J. Organomet. Chem. 2014, 758, 65.
[42] Gregson, C. K. A.; Blackmore, I. J.; Gibson, V. C.; Long, N. J.; Marshall, E. L.; White, A. J. P. Dalton Trans. 2006, 3134.
[43] Lee, J.; Kim, Y.; Do, Y. Inorg. Chem. 2007, 46, 7701.
[44] Chmura, A. J.; Cousins, D. M.; Davidson, M. G.; Jones, M. D.; Lunn, M. D.; Mahonc, M. F. Dalton Trans. 2008, 1437.
[45] Zhang, F.; Song, H.; Zi, G. J. Organomet. Chem. 2010, 695, 1993.
[46] Saha, T. K.; Ramkumar, V.; Chakraborty, D. Inorg. Chem. 2011, 50, 2720.
[47] Deivasagayam, D.; Peruch, F. Polymer 2011, 52, 4686.
[48] Zhao, N.; Hou, G.; Deng, X.; Zi, G.; Walter, M. D. Dalton Trans. 2014, 43, 8261.
[49] Peng, Y.-L.; Huang, Y.; Chuang, H.-J.; Kuo, C.-Y.; Lin, C.-C. Polymer 2010, 51, 4329.
[50] Davin, J. P.; Buffet, J.-C.; Spaniol, T. P.; Okuda, J. Dalton Trans. 2012, 41, 12612.
[51] Wang, H.; Yang, Y.; Ma, H. Macromolecules 2014, 47, 7750.
[52] Fecker, A. C.; Freytag, M.; Jones, P. G.; Zhao, N.; Zi, G.; Walter, M. D. Dalton Trans. 2015, 44, 16325.
[53] Rosen, T.; Goldberg, I.; Venditto, V.; Kol, M. J. Am. Chem. Soc. 2016, 138, 12041.
[54] Buffet, J.-C.; Okuda, J.; Arnold, P. L. Inorg. Chem. 2010, 49, 419.
[55] Yu, I.; Acosta-Ramírez, A.; Mehrkhodavandi, P. J. Am. Chem. Soc. 2012, 134, 12758.
[56] Aluthge, D. C.; Patrick, B. O.; Mehrkhodavandi, P. Chem. Commun. 2013, 49, 4295.
[57] Hayatifar, M.; Marchetti, F.; Pampaloni, G.; Zacchini, S. Inorg. Chem. 2013, 52, 4017.
[58] Kang, Y. Y.; Park, H.-R.; Lee, M. H.; An, J.; Kim, Y.; Lee, J. Polyhedron 2015, 95, 24.

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