Citation: Zhao Ning. Progress in Ring Opening Polymerization of Lactides Catalyzed by Chiral Organometallic Complexes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1139-1159. doi: 10.6023/cjoc201612011 shu

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

Zhao Ning ^*,,

College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021

Corresponding author: Zhao Ning, zhaoninghg@sust.edu.cn
Received Date: 4 December 2016
Revised Date: 17 January 2017

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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.
- chiral organometallic complexes,
- catalysis,
- polymerization of lactides
1. [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. [2]
3. [3]
  Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1316. doi: 10.1021/ja012052+
4. [4]
5. [5]
  Chisholm, M. H.; Eilerts, N. W.; Huffman, J. C.; Iyer, S. S.; Pacold, M.; Phomphrai, K. J. Am. Chem. Soc. 2000, 122, 11845. doi: 10.1021/ja002160g
6. [6]
  Labourdette, G.; Lee, D. J.; Patrick, B. O.; Ezhova, M. B.; Mehrkhodavandi, P. Organometallics 2009, 28, 1309. doi: 10.1021/om800818v
7. [7]
  Drouin, F.; Oguadinma, P. O.; Whitehorne, T. J. J.; Prud'homme, R. E.; Schaper, F. Organometallics 2010, 29, 2139. doi: 10.1021/om100154w
8. [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. doi: 10.1016/j.inoche.2009.12.024
9. [9]
  Darensbourg, D. J.; Karroonnirun, O. Inorg. Chem. 2010, 49, 2360. doi: 10.1021/ic902271x
10. [10]
  Pastor, M. F.; Whitehorne, T. J. J.; Oguadinma, P. O.; Schaper, F. Inorg. Chem. Commun. 2011, 14, 1737. doi: 10.1016/j.inoche.2011.07.018
11. [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. doi: 10.1021/om300146n
12. [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. [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. doi: 10.1021/om4003279
14. [14]
  Wang, H.; Ma, H. Chem. Commun. 2013, 49, 8686. doi: 10.1039/c3cc44980g
15. [15]
  Honrado, M.; Otero, A.; Fernández-Baeza, J.; Sánchez-Barba, L. F.; Garcés, A.; Lara-Sańchez, A.; Rodríguez, A. M. Organometallics 2014, 33, 1859. doi: 10.1021/om500207x
16. [16]
  Abbina, S.; Du, G. ACS Macro Lett. 2014, 3, 689. doi: 10.1021/mz5002959
17. [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. doi: 10.1016/j.poly.2014.08.067
18. [18]
  Spassky, N.; Wisniewski, M.; Pluta, C.; Borgne, A. L. Macromol. Chem. Phys. 1996, 197, 2627. doi: 10.1002/macp.1996.021970902
19. [19]
  Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072. doi: 10.1021/ja990088k
20. [20]
  Zhong, Z.; Dijkstra, P. J.; Feijen, J. Angew. Chem., Int. Ed. 2002, 41, 4510. doi: 10.1002/1521-3773(20021202)41:23<4510::AID-ANIE4510>3.0.CO;2-L
21. [21]
  Zhong, Z.; Dijkstra, P. J.; Feijen, J. J. Am. Chem. Soc. 2003, 125, 11291. doi: 10.1021/ja0347585
22. [22]
  Bouyahyi, M.; Grunova, E.; Marquet, N.; Kirillov, E.; Thomas, C. M.; Roisnel, T.; Carpentier, J.-F. Organometallics 2008, 27, 5815. doi: 10.1021/om800651z
23. [23]
  Du, H.; Velders, A. H.; Dijkstra, P. J.; Sun, J.; Zhong, Z.; Chen, X.; Feijen, J. Chem. Eur. J. 2009, 15, 9836. doi: 10.1002/chem.v15:38
24. [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. doi: 10.1039/c3dt32657h
25. [25]
  Gao, B.; Duan, R.; Pang, X.; Li, X.; Qu, Z.; Tang, Z.; Zhuang, X.; Chen, X. Organometallics 2013, 32, 5435. doi: 10.1021/om400714q
26. [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. [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. [28]
  Pilone, A.; Press K.; Goldberg, I.; Kol, M.; Mazzeo, M.; Lamberti, M. J. Am. Chem. Soc. 2014, 136, 2940. doi: 10.1021/ja412798x
29. [29]
  Go, M. J.; Kim, S. H.; Kang, Y. Y.; Park, H.-R.; Kim, Y.; Lee, J. Inorg. Chem. Commun. 2014, 44, 139. doi: 10.1016/j.inoche.2014.03.008
30. [30]
  Bian, S.; Abbina, S.; Lu, Z.; Kolodka, E.; Du, G. Organometallics 2014, 33, 2489. doi: 10.1021/om401226j
31. [31]
  Gao, B.; Li, D.; Duan, Q.; Duan, R.; Pang, X. New J. Chem. 2015, 39, 4670. doi: 10.1039/C5NJ00469A
32. [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. doi: 10.1021/ma990005k
33. [33]
  Alaaeddine, A.; Amgoune, A.; Thomas, C. M.; Da gorne, S.; Bellemin-Laponnaz, S.; Carpentier, J.-F. Eur. J. Inorg. Chem. 2006, 3652.
34. [34]
  Heck, R.; Schulz, E.; Collin, J.; Carpentier, J.-F. J. Mol. Catal. A: Chem. 2007, 268, 163. doi: 10.1016/j.molcata.2006.12.030
35. [35]
  Platel, R. H.; White, A. J. P.; Williams, C. K. Inorg. Chem. 2008, 47, 6840. doi: 10.1021/ic800419t
36. [36]
  Zi, G.; Wang, Q.; Xiang, L.; Song, H. Dalton Trans. 2008, 5930.
37. [37]
  Wang, Q.; Xiang, L.; Song, H.; Zi, G. J. Organomet. Chem. 2009, 694, 691. doi: 10.1016/j.jorganchem.2008.11.061
38. [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. doi: 10.1002/anie.v48:12
39. [39]
  Zhang, F.; Zhang, J.; Song, H.; Zi, G. Inorg. Chem. Commun. 2011, 14, 72. doi: 10.1016/j.inoche.2010.09.034
40. [40]
  Kratsch, J.; Kuzdrowska, M.; Schmid, M.; Kazeminejad, N.; Kaub, C.; Oña-Burgos, P.; Guillaume, S. M.; Roesky, P. W. Organometallics 2013, 32, 1230. doi: 10.1021/om301011v
41. [41]
  Ren, W.; Chen, L.; Zhao, N.; Wang, Q.; Hou, G.; Zi, G. J. Organomet. Chem. 2014, 758, 65. doi: 10.1016/j.jorganchem.2014.02.005
42. [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. [43]
  Lee, J.; Kim, Y.; Do, Y. Inorg. Chem. 2007, 46, 7701. doi: 10.1021/ic700493p
44. [44]
  Chmura, A. J.; Cousins, D. M.; Davidson, M. G.; Jones, M. D.; Lunn, M. D.; Mahonc, M. F. Dalton Trans. 2008, 1437.
45. [45]
  Zhang, F.; Song, H.; Zi, G. J. Organomet. Chem. 2010, 695, 1993. doi: 10.1016/j.jorganchem.2010.05.003
46. [46]
  Saha, T. K.; Ramkumar, V.; Chakraborty, D. Inorg. Chem. 2011, 50, 2720. doi: 10.1021/ic1025262
47. [47]
  Deivasagayam, D.; Peruch, F. Polymer 2011, 52, 4686. doi: 10.1016/j.polymer.2011.07.049
48. [48]
  Zhao, N.; Hou, G.; Deng, X.; Zi, G.; Walter, M. D. Dalton Trans. 2014, 43, 8261. doi: 10.1039/C4DT00510D
49. [49]
  Peng, Y.-L.; Huang, Y.; Chuang, H.-J.; Kuo, C.-Y.; Lin, C.-C. Polymer 2010, 51, 4329. doi: 10.1016/j.polymer.2010.07.016
50. [50]
  Davin, J. P.; Buffet, J.-C.; Spaniol, T. P.; Okuda, J. Dalton Trans. 2012, 41, 12612. doi: 10.1039/c2dt31309j
51. [51]
  Wang, H.; Yang, Y.; Ma, H. Macromolecules 2014, 47, 7750. doi: 10.1021/ma501896r
52. [52]
  Fecker, A. C.; Freytag, M.; Jones, P. G.; Zhao, N.; Zi, G.; Walter, M. D. Dalton Trans. 2015, 44, 16325. doi: 10.1039/C5DT02851E
53. [53]
  Rosen, T.; Goldberg, I.; Venditto, V.; Kol, M. J. Am. Chem. Soc. 2016, 138, 12041. doi: 10.1021/jacs.6b07287
54. [54]
  Buffet, J.-C.; Okuda, J.; Arnold, P. L. Inorg. Chem. 2010, 49, 419. doi: 10.1021/ic900740n
55. [55]
  Yu, I.; Acosta-Ramírez, A.; Mehrkhodavandi, P. J. Am. Chem. Soc. 2012, 134, 12758. doi: 10.1021/ja3048046
56. [56]
  Aluthge, D. C.; Patrick, B. O.; Mehrkhodavandi, P. Chem. Commun. 2013, 49, 4295. doi: 10.1039/C2CC33519K
57. [57]
  Hayatifar, M.; Marchetti, F.; Pampaloni, G.; Zacchini, S. Inorg. Chem. 2013, 52, 4017. doi: 10.1021/ic4000654
58. [58]
  Kang, Y. Y.; Park, H.-R.; Lee, M. H.; An, J.; Kim, Y.; Lee, J. Polyhedron 2015, 95, 24. doi: 10.1016/j.poly.2015.04.006
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