Facile and efficient synthesis of cyclic anhydrides from dicarboxylic acids

ACS Catalysis

Volumn 4, Issue 10, 2014, Pages 3586-3589

  Robert, Carine ^a   De Montigny, Frédéric ^a   Thomas, Christophe M ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

catalysis; cyclic anhydride; cyclization; dicarboxylic acid; magnesium

Indexed keywords

CYCLIZATION; MAGNESIUM;

CYCLIC ANHYDRIDE; DICARBOXYLIC ACID; EFFICIENT SYNTHESIS;

CATALYSIS;

EID: 84907809565     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs501237p     Document Type: Article

References (37)

1. Okada, M. Prog. Polym. Sci. 2002, 27, 87-133
2. Rass-Hansen, J.; Falsig, H.; Jorgensen, B.; Christensen, C. H. J. Chem. Technol. Biotechnol. 2007, 82, 329-333
3. Weisz, P. B. Phys. Today 2004, 57, 47-52
4. Williams, C. K.; Hillmyer, M. A. Polym. Rev. 2008, 48, 1-10
5. Zaldivar, J.; Nielsen, J.; Olsson, L. Appl. Microbiol. Biotechnol. 2001, 56, 17-34
6. Gerngross, T. U.; Slater, S. C. Sci. Am. 2000, 283, 36-41
7. Gross, R. A.; Kalra, B. Science 2002, 297, 803-807
8. Danner, H.; Braun, R. Chem. Soc. Rev. 1999, 28, 395-405
9. Anastas, P. T.; Warner, J. C. In Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998; pp 11-30.
10. Vennestrøm, P. N. R.; Osmundsen, C. M.; Christensen, C. H.; Taarning, E. Angew. Chem., Int. Ed. 2011, 50, 10502-10509
11. Azadi, P.; Carrasquillo-Flores, R.; Pagán-Torres, Y. J.; Gürbüz, E. I.; Farnood, R.; Dumesic, J. A. Green Chem. 2012, 14, 1573-1576
12. Gallezot, P. Chem. Soc. Rev. 2012, 41, 1538-1558
13. Deuss, P. J.; Barta, K.; de Vries, J. G. Catal. Sci. Technol. 2014, 4, 1174-1196
14. Perego, C.; Riccia, M. Catal. Sci. Technol. 2012, 2, 1776-1786
15. Poliakoff, M.; Licence, P. Nature 2007, 450, 810-812
16. Ragauskas, A. J.; Williams, C. K.; Davison, B. H.; Britovsek, G.; Cairney, J.; Eckert, C. A.; Frederick, W. J., Jr.; Hallett, J. P.; Leak, D. J.; Liotta, C. L.; Mielenz, J. R.; Murphy, R.; Templer, R.; Tschaplinski, T. Science 2006, 311, 484-489
17. Güner, F. S.; Yagci, Y.; Erciyes, A. T. Prog. Polym. Sci. 2006, 31, 633-670
18. Jenck, J. F.; Agterberg, F.; Droescher, M. J. Green Chem. 2004, 6, 544-556
19. Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411-2502
20. Biermann, U.; Friedt, W.; Lang, S.; Lühs, W.; Machmüller, G.; Metzger, J. O.; Rüsch Gen Klaas, M.; Schäfer, H. J.; Schneider, M. P. Angew. Chem., Int. Ed. 2000, 39, 2206-2224
21. Lucia, L. A.; Argyropoulos, D. S.; Adamopoulos, L.; Gaspar, A. R. Can. J. Chem. 2006, 84, 960-970
22. Tschan, M. J. L.; Brule, E.; Haquette, P.; Thomas, C. M. Polym. Chem. 2012, 3, 836-851
23. Coates, G. W.; Hillmyer, M. A. Macromolecules 2009, 42, 7987-7989
24. Gandini, A. Macromolecules 2008, 41, 9491-9504
25. Meier, M. A. R.; Metzger, J. O.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1788-1802
26. Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044-4098
27. Sauer, M.; Porro, D.; Mattanovich, D.; Branduardi, P. Trends Biotechnol. 2008, 26, 100-108
28. Their overall production cost still remains to be reduced in order to be competitive with petrochemical-derived chemicals: Bechthold, I.; Bretz, K.; Kabasci, S.; Kopitzky, R.; Springer, A. Chem. Eng. Technol. 2008, 31, 647-654
29. Robert, C.; de Montigny, F.; Thomas, C. M. Nat. Commun. 2011, 10.1038 / ncomms1596
30. Bartoli, G.; Bosco, M.; Carlone, A.; Dalpozzo, R.; Mercantoni, E.; Melchiorre, P.; Sembri, L. Synthesis 2007, 22, 3489-3496
31. Takeda, K.; Akiyama, A.; Nakamura, H.; Takizawa, S.; Mizuno, Y.; Takayanagi, H.; Harigaya, Y. Synthesis 1994, 10, 1063-1066
32. Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2005, 127, 13798-13799
33. Coulembier, O.; Sanders, D. P.; Nelson, A.; Hollenbeck, A. N.; Horn, A. W.; Rice, J. E.; Fujiwara, M.; Dubois, P.; Hedrick, J. L. Angew. Chem. 2009, 121, 5272-5275
34. Watanabe, K.; Yamagiwa, N.; Torisawa, Y. Org. Process. Res. Dev. 2007, 11, 251-258
35. Aycock, D. Org. Process. Res. Dev. 2007, 11, 156-159
36. Mestres, R.; Palomo, C. Synthesis 1981, 218-220
37. Balasubramaniya, V.; Bhatia, V. G.; Wagh, S. B. Tetrahedron 1983, 39, 1475-1485