Single-component catalyst/initiators for the organocatalytic ring-opening polymerization of lactide

Journal of the American Chemical Society

Volumn 127, Issue 25, 2005, Pages 9079-9084

  Csihony, Szilard ^a   Culkin, Darcy A ^a   Sentman, Alan C ^b   Dove, Andrew P ^b   Waymouth, Robert M ^a   Hedrick, James L ^b  

^a STANFORD UNIVERSITY   (United States)

^b IBM ALMADEN RESEARCH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHARACTERIZATION; MOLECULAR WEIGHT; POLYMERS; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

ADDUCTS; CARBENE; COMPLEX ARCHITECTURES; POLYDISPERSITIES;

CATALYSTS;

1,3 DIMESITYLIMIDAZOLIN 2 YLIDENE; ALCOHOL; POLYLACTIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; MOLECULAR WEIGHT; POLYMERIZATION; RING OPENING METATHESIS POLYMERIZATION; ROOM TEMPERATURE; SYNTHESIS;

ALCOHOLS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; IMIDAZOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYESTERS;

EID: 21244490732     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050909n     Document Type: Article

References (52)

1. Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181-222.
2. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
3. Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951-961.
4. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130-5135.
5. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
6. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899-1902.
7. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124. 10298-10299.
8. Kerr, M. S.; Rovis, T. Synlett 2003, 1934-1936.
9. Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876-8877.
10. Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221.
11. Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925-2928.
12. Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1998, 1891-1893.
13. Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745.
14. Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432-8433.
15. Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587-3590.
16. Grasa, G.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583-3586.
17. Grasa, G. A.; Guveli, T.; Singh, R.; Nolan, S. P. J. Org. Chem. 2003, 68, 2812-2819.
18. Singh, R.; Kissling, R. M.; Letellier, M. A.; Nolan, S. P. J. Org. Chem. 2004, 69, 209-212.
19. Chow, K. Y. K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126-8127.
20. Reynolds, N. T.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518-9519.
21. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370-14371.
22. Duong, H. A.; Cross, M. J.; Louie, J. Org. Lett. 2004, 6, 4679-4681.
23. Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
24. Canac, Y.; Soleilhavoup, M.; Conejero, S.; Bertrand, G. J. Organomet. Chem. 2004, 689, 3857-3865.
25. Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hednck, J. L. J. Am. Chem. Soc. 2002, 124, 914-915.
26. Nyce, G. W.; Glauser, T.; Connor, E. F.; Mock, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 125, 3046-3056.
27. Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147-6176.
28. Lofgren, A.; Albertsson, A. C.; DuBois, P.; Jerome, R. J. Macromol. Sci. Rev. 1995, C35, 379-418.
29. Nouvel, C.; Dubois, P.; Dellacherie, E.; Six, J. L. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 2577-2588.
30. Penczek, S.; Biela, T.; Duda, A. Macromol. Rapid Commun. 2000, 21, 941-950.
31. Nyce, G. W.; Csihony, S.; Waymouth, R. M.; Hedrick, J. L. Chem.-Eur. J. 2004, 10, 4073-4079
32. (a) Lachmann, B.; Wanzlick, H. W. Liebigs Ann. Chem. 1969, 729, 27-32.
33. (b) Hoffmann, R. W.; Hagenbruch, B.; Smith, D. M. Chem. Ber. 1977, 110, 23-36.
34. (c) Csihony, S.; Beaudette, T. T.; Sentman, A. C.; Nyce, G.; Waymouth, R. M.; Hedrick, J. L. Adv. Synth. Catal. 2004, 346, 1081-1086.
35. Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. 1995, 34, 1021-1023.
36. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Liebigs Ann. Chem. 1996, 2019-2028.
37. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
38. Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155.
39. Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T. L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 2546-2558.
40. Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechen, S. Angew. Chem., Int. Ed. 2000, 39, 3898-3901.
41. Denk, K.; Sirsch, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219-224.
42. Arduengo, A. J., III; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028.
43. Wanzlick, H. W.; Lachmann, B.; Schikora, E. Chem. Ber. 1965, 98, 3170.
44. See Supporting Information.
45. Arduengo, A. J.; Calabrese, J. C.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Krafczyk, R.; Marshall, W. J.; Tamm, M.; Schmutzler, R. Helv. Chim. Acta 1999, 82, 2348-2364.
46. Kuhn, N.; Bohnen, H.; Henkel, G. Z. Naturforsch., B: Chem. Sci. 1994, 49, 1473-1480.
47. Schössler, W.; Regitz, G. Chem. Ber. 1974, 107, 1931-1948.
48. Duong, H. A.; Tekavec, T. N.; Arif, A. M.; Louie, J. Chem. Commun. 2004, 112-113.
49. Matyjaszewski, K. Macromol. Symp. 2001, 174, 51-67.
50. Matyjaszewski, K., Ed. Controlled Radical Polymerization; American Chemical Society: Washington, DC, 1998; Vol. 685.
51. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688.
52. Arduengo, A. J.; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523-14534.