Tetra- N -Butylammonium fluoride as an efficient transesterification catalyst for functionalizing cyclic carbonates and aliphatic polycarbonates

ACS Macro Letters

Volumn 2, Issue 10, 2013, Pages 860-864

  Chan, Julian M W ^a   Sardon, Haritz ^a,b   Engler, Amanda C ^a   García, Jeannette M ^a   Hedrick, James L ^a  

^a IBM ALMADEN RESEARCH CENTER   (United States)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84885966275     PISSN: None     EISSN: 21611653     Source Type: Journal    
DOI: 10.1021/mz400334j     Document Type: Article

References (35)

1. Kiesewetter, M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M. Macromolecules 2010, 43, 2093-2107
2. Dove, A. P. Chem. Commun. 2008, 6446-6470
3. Kobayashi, S. Macromol. Rapid Commun. 2009, 30, 237-266
4. Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813-5840
5. Coulembier, O.; Degée, P.; Hedrick, J. L.; Dubois, P. Prog. Polym. Sci. 2006, 31, 723-747
6. Matsumura, S. Enzymatic Synthesis of Polyesters via Ring-Opening Polymerization. In Enzyme-Catalyzed Synthesis of Polymers; Kobayashi, S.; Ritter, H.; Kaplan, D., Eds.; Springer: Berlin/Heidelberg, 2006; Vol. 194, pp 95-132.
7. Varma, I. K.; Albertsson, A.-C.; Rajkhowa, R.; Srivastava, R. K. Prog. Polym. Sci. 2005, 30, 949-981
8. Stridsberg, K.; Ryner, M.; Albertsson, A.-C. Controlled Ring-Opening Polymerization: Polymers with Designed Macromolecular Architecture. In Degradable Aliphatic Polyesters; Springer: Berlin/Heidelberg, 2002; Vol. 157, pp 41-65.
9. Endo, T.; Shibasaki, Y.; Sanda, F. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2190-2198
10. Mecerreyes, D.; Jéroîme, R.; Dubois, P. Novel Macromolecular Architectures Based on Aliphatic Polyesters: Relevance of the "Coordination-Insertion" Ring-Opening Polymerization. In Macromolecular Architectures; Hilborn, J.; Dubois, P.; Hawker, C.; Hedrick, J.; Hilborn, J.; Jéroîme, R.; Kiefer, J.; Labadie, J.; Mecerreyes, D.; Volksen, W., Eds.; Springer: Berlin/Heidelberg, 1999; Vol. 147, pp 1-59.
11. Nederberg, F.; Zhang, Y.; Tan, J. P. K.; Xu, K.; Wang, H.; Yang, C.; Gao, S.; Guo, X. D.; Fukushima, K.; Li, L.; Hedrick, J. L.; Yang, Y.-Y. Nat. Chem 2011, 3, 409-414
12. Hedrick, J. L.; Nelson, A.; Sanders, D. P. Method of preparing cyclic carbonates, cyclic carbamates, cyclic ureas, cyclic thiocarbonates, cyclic thiocarbamates, and cyclic dithiocarbonates. U.S. Patent 20100280242, 2010.
13. Suriano, F.; Pratt, R.; Tan, J. P. K.; Wiradharma, N.; Nelson, A.; Yang, Y.-Y.; Dubois, P.; Hedrick, J. L. Biomaterials 2010, 31, 2637-2645
14. Xie, Z.; Hu, X.; Chen, X.; Sun, J.; Shi, Q.; Jing, X. Biomacromolecules 2007, 9, 376-380
15. Tempelaar, S.; Barker, I. A.; Truong, V. X.; Hall, D. J.; Mespouille, L.; Dubois, P.; Dove, A. P. Polym. Chem 2013, 4, 174-183
16. Fujiwara, M.; Hedrick, J. L.; Sanders, D. P.; Yasumoto, M. Cyclic carbonyl compounds with pendant carbonate groups, preparations thereof, and polymers therefrom. U.S. Patent 20110269917, 2011.
17. Coulembier, O.; Hedrick, J. L.; Nelson, A.; Rice, J. E.; Sanders, D. P. Method of ring-opening polymerization, and related compositions and articles. U.S. Patent 20100305300, 2010.
18. Tempelaar, S.; Mespouille, L.; Coulembier, O.; Dubois, P.; Dove, A. P. Chem. Soc. Rev. 2013, 42, 1312-1336
19. Chen, W.; Yang, H.; Wang, R.; Cheng, R.; Meng, F.; Wei, W.; Zhong, Z. Macromolecules 2009, 43, 201-207
20. Onbulak, S.; Tempelaar, S.; Pounder, R. J.; Gok, O.; Sanyal, R.; Dove, A. P.; Sanyal, A. Macromolecules 2012, 45, 1715-1722
21. Tempelaar, S.; Mespouille, L.; Dubois, P.; Dove, A. P. Macromolecules 2011, 44, 2084-2091
22. Williams, R. J.; Barker, I. A.; O'Reilly, R. K.; Dove, A. P. ACS Macro Lett. 2013, 1, 1285-1290
23. Zhou, Y.; Zhuo, R.-X.; Liu, Z.-L. Macromol. Rapid Commun. 2005, 26, 1309-1314
24. Gibson, M. I.; Fröhlich, E.; Klok, H.-A. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 4332-4345
25. Engler, A. C.; Chan, J. M. W.; Coady, D. J.; O'Brien, J. M.; Sardon, H.; Nelson, A.; Sanders, D. P.; Yang, Y. Y.; Hedrick, J. L. Macromolecules 2013, 46, 1283-1290
26. Sanders, D. P.; Fukushima, K.; Coady, D. J.; Nelson, A.; Fujiwara, M.; Yasumoto, M.; Hedrick, J. L. J. Am. Chem. Soc. 2010, 132, 14724-14726
27. Engler, A. C.; Chan, J. M. W.; Fukushima, K.; Coady, D. J.; Yang, Y. Y.; Hedrick, J. L. ACS Macro Lett. 2013, 2, 332-336
28. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. 1978, 17, 569-583
29. Connors, K. A.; Pandit, N. K. Anal. Chem. 1978, 50, 1542-1545
30. Qiao, Y.; Yang, C.; Coady, D. J.; Ong, Z. Y.; Hedrick, J. L.; Yang, Y.-Y. Biomaterials 2012, 33, 1146-1153
31. Coady, D. J.; Engler, A. C.; Fukushima, K.; Hedrick, J. L.; Tan, J. P. K.; Yang, Y. Y. Cationic polymers for antimicrobial applications and delivery of bioactive materials. U.S. Patent 20120251608, 2012.
32. Lippert, J. W., III ARKIVOC 2005, 14, 87-95
33. Szewczyk, J.; Lejczak, B.; Kafarski, P. Synthesis 1982, 1982, 409-412
34. Saegusa, T.; Kobayashi, S.; Kimura, Y. J. Chem. Soc., Chem. Commun. 1976, 443a-443a
35. Ogilvie, K. K.; Beaucage, S. L. J. Chem. Soc., Chem. Commun. 1976, 443b-444