(Thio)amidoindoles and (Thio)amidobenzimidazoles: An investigation of their hydrogen-bonding and organocatalytic properties in the ringopening polymerization of lactide

Chemistry - A European Journal

Volumn 16, Issue 14, 2010, Pages 4196-4205

  Koeller, Sylvain ^a   Kadota, Joji ^b   Peruch, Frédéric ^b   Deffieux, Alain ^b   Pinaud, Noel ^a   Pianet, Isabelle ^a   Massip, Stéphane ^a   Léger, Jean Michel ^a   Desvergne, Jean Pierre ^a   Bibal, Brigitte ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b Ecole Nationale Superieure de Chimie et de Physique de Bordeaux   (France)

Author keywords

Hydrogen bonds; Lactides; Organocatalysis; Partner catalysts; Ring opening polymerization

Indexed keywords

AMIDES; ASSOCIATION REACTIONS; CATALYSIS; CATALYSTS; RING OPENING POLYMERIZATION;

CATALYTIC PROPERTIES; CONVERSION YIELD; DYNAMIC EQUILIBRIA; INTERMOLECULAR INTERACTIONS; LACTIDES; ORGANOCATALYSIS; SELF-ASSOCIATIONS; WEAK HYDROGEN BOND;

HYDROGEN BONDS;

EID: 77950847433     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902912     Document Type: Article

References (68)

1. a) F. Nederberg, E. F. Connor, M. Möller, T. Glauser, J. L. Hedrick, Angew. Chem. 2001, 113, 2784-2787;
2. Angew. Chem. Int. Ed. 2001, 40, 2712-2715;
3. b) N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. G. Lohmeijer, J. L. Hedrick, Chem. Rev. 2007, 107, 5813-5840;
4. c) D. Bourissou, S. Moebs-Sanchez, B. Martin-Vaca, C. R. Chim. 2007, 10, 775-794;
5. d) A. P. Dove, Chem. Commun. 2008, 6446-6470.
6. a) F. Nederberg, B. G. G. Lohmeijer, F. Leiblarth, R. C. Pratt, J. Choi, A. P. Dove, R. M. Waymouth, J. L. Hedrick, Biomacromolecules 2007, 8, 153-160;
7. b) R. C Pratt, F. Nederberg, R. M. Waymouth, J. L. Hedrick, Chem. Commun. 2008, 114-116.
8. a) H. R. Kricheldorf, I. Kreiser, Makromol. Chem. 1987, 188, 1861-1873;
9. b) F. Sanda, H. Sanada, Y. Shibasaki, T. Endo, Macromolecules 2002, 35, 680-683;
10. c) X. Lou, C. Detrembleur, R. Jérôme, Macromolecules 2002, 35, 11.90-1195;
11. P.V. Persson, J. Schröder, K. Wickholm, E. Hedenström, T. Iversen, Macromolecules 2004, 37, 5889-5893;
12. e) S. Gazeau-Bureau, D. Delcroix, B. Martin-Vaca, D. Bourissou, C. Navarro, S. Magnet, Macromolecules 2008, 41, 3782-3784.
13. O. Coulembier, D. P. Sanders, A. Nelson, A. N. Hollenbeck, H. W. Horn, J. E. Rice, M. Fujiwara, P. Dubois, J. L. Hedrick, Angew. Chem 2009, 121, 5272-5275;
14. Angew. Chem. Int. Ed. 2009, 48, 5170-5173.
15. a) F. Nederberg, E. F. Connor, T. Glauser, J. L. Hedrick, Chem. Commun. 2001, 2066-2067;
16. b) reference [1a].
17. M. Myers, E. F. Connor, T. Glauser, A. Mock, G. Nyce, J. L. He-drick, J. Polym. Sci. Polym. Chem. Ed. 2002, 40, 844-851.
18. a) E. F. Connor, G. W. Nyce, M. Myers, A. Möck, J. L. Hedrick, J. Am. Chem. Soc. 2002, 124, 914-915;
19. b) O. Coulembier, B. G. G. Lohmeijer, A. P. Dove, R. C Pratt, L. Mespouille, D. A. Culkin, S. J. Benight, P. Dubois, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 5617-5628;
20. d) A. P. Dove, R. C Pratt, B. G. G. Lohmeijer, D. A. Culkin, E. C. Hagberg, G. W Nyce, R. M. Waymouth, J. L. Hedrick, Polymer 2006, 47, 4018-4025;
21. e) W. Jeong, J. L. Hedrick, R. M. Waymouth, J. Am. Chem. Soc. 2007, 129, 8414-8415.
22. a) L. Zhang, F. Nederberg, R. C. Pratt, R. M. Waymouth, J. L. Hedrick, C. G. Wade, Macromolecules 2007, 40, 4154-4158;
23. b) L. Zhang, F. Nederberg, J. M. Messman, R. C. Pratt, J. L. Hedrick, C. G. Wade, J. Am. Chem. Soc. 2007, 129, 12610-12611.
24. a) R. C. Pratt, B. G. G. Lohmeijer, D. A. Long, R. M. Waymouth, J. L. Hedrick, J. Am. Chem. Soc. 2006, 128, 4556-4557;
25. b) B. G. G. Lohmeijer, R. C. Pratt, F. Leibfarth, J. W Logan, D. A. Long, A. P. Dove, F. Nederberg, J. Choi, C. G. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 8574-8583;
26. c) X. Sun, J. P. Gao, Z. Y. Wang, J. Am. Chem. Soc. 2008, 130, 8130-8131.
27. a) A. P. Dove, R. C Pratt, B. G. G. Lohmeijer, R. M. Waymouth, J. L. Hedrick, J. Am. Chem. Soc. 2005, 127, 13798-13799;
28. b) R.C. Pratt, B. G. G. Lohmeijer, D. A. Long, P. N. P. Lundberg, A. P. Dove, H. Li, C. G. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 7863-7871.
29. A. Chuma, H. W. Horn, W. C. Swope, R. C. Pratt, L. Zhang, B. G. G. Lohmeijer, C. G. Wade, R. M. Waymouth, J. L. Hedrick, J. E. Rice, J. Am Chem. Soc. 2008, 130, 6749-6754.
30. Recent reviews about bifunctional thioureas: a) Y. Takemoto Org. Biomol. Chem. 2005, 3, 4299-4306;
31. b) A. Berkessel, F. Cleemann, S. Mukherjee, T. N. Müller, J. Lex, Angew. Chem. 2005, 117, 817-821;
32. Angew. Chem. Int. Ed. 2005, 44, 807-811;
33. c) M.. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573;
34. Angew. Chem,. Int. Ed. 2006, 45, 1520-1543;
35. d) S. J. Connon, Chem. Eur. J. 2006, 12, 5418-5427.
36. a) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673;
37. b) Y. Hoashi, T. Okino, Y. Takemoto, Angew. Chem,. 2005, 117, 4100-4103;
38. Angew. Chem. Int. Ed. 2005, 44, 4032-4035.
39. a) C Givelet, B. Tinant, L. Van Meerveit, T. Buffeteau, N. Marchand-Geneste, B. .Bibal, J. Org. Chem. 2009, 74, 652-659;
40. b) M.-L. Dumartin, C Givelet, P. Meyrand, B. Bibal, I. Gosse, Org. Biomol. Chem. 2009, 7, 2725-2728;
41. c) C. Givelet, T. Buffeteau, F. ArnaudNeu, V. Hubscher-Bruder, B. Bibal, J. Org. Chem. 2009, 74, 5059-5062.
42. S. Koeller, J. Kadota, A. Deffieux, F. Peruch, S. Massip, J.-M. Léger, J.-P. Desvergne, B. Bibal, J. Am. Chem. Soc. 2009, 131, 1508815089.
43. Adapted from: C. Kuehm-Caubère, P. Caubère, B. Jamart-Grégoire, A. Negre-Salvayre, D. Bonnefont-Rousselot, J.-G. Bizot-Espiard, B. Pfeiffer, D.-H. Caignard, B. Guardiola-Lemaître, P. Renard, J. Med. Chem. 1997, 40, 1201-1210.
44. Adapted from: J. Sluka, J. Danek, P. Bedrnik, Z. Budesinsky, Collect. Czech. Chem. Commun. 1981, 46, 2703-2708.
45. N. J. Leonard, D. Y. Curtin, K. M. Beck, J. Am. Chem. Soc. 1947, 69, 2459-2461.
46. a) M. Jesberger, T.P. Davis, L. Barner, Synthesis 2003, 1929-1958;
47. b)T. Ozturk, E. Ertas, O. Mert, Chem. Rev. 2007, 107, 5210-5218.
48. a) E. V. Nosova, G. N. Lipunova, A. A. Laeva, V. N. Charushin, Russ. I. Org. Chem. 2005, 41, 1671-1677;
49. b) J. P. Powers, S. Li, J. C. Jaen, J. Liu, N. P. C. Walker, Z. Wang, H. Wesche, Bioorg. Med. Chem. Lett. 2006, 16, 2842-2845.
50. a) S. Ianelli, M. Nardelli, D. Belletti, B. Jamart-Grégoire, C. Caubère, P. Caubère, Acta Crystallogr. Sect. C 1995, 51, 1341.-1345;
51. b) G. W. Bates, M. E. Light, M. Albrecht, P. A. Gale, J. Org. Chem,. 2007, 72, 8921-8927.
52. a) J. Li, D.-Q. Shi, W.-X. Chen, Heterocycles 1997, 45, 2381-2384;
53. b) L. Jing, F. He-Liang, S. Jie, C. Wei-Xing, Acta Crystallogr. Sect. C 1997, 53, 320-322.
54. a) B. Yang, Y.-F. Xia, S. Bi, S.-S. Zhang, Acta Crystallogr. Sect. E 2006, 62, 04200-o4202;
55. b)M..G. Fisher, P.A. Gale, M.E. Light, New J. Chem. 2007, 31, 1583-1.584.
56. a) L. Leiserowitz, G. M, X Schmidt, J. Chem,. Soc. A 1969, 2372-2382;
57. b) L. Leiserowitz, M. Tuval, Acta Crystallogr. Sect. B 1978, 34, 1230-1247;
58. P. Dauber, A. T. Haggler, Acc. Chem. Res. 1980, 13, 105-112;
59. d) R. Taylor, O. Kennard, W. Versichel, Acta Crystallogr. Sect. B 1984, 40, 280-288;
60. e) M. C. Etter, Acc. Chem. Res. 1990, 23, 120-126.
61. a) C. N. Sundaresan, S. Dixit, P. Venugopalan, J. Mol Struct. 2004, 693, 205-209;
62. b) G. Pavlovic, V. Tralic-Kulenovic, M. Vinkovic, D. Vikic-Topic, I. Matanovic, Z. Popovic, Struct. Chem. 2006, 17, 275-285.
63. a) T. Sifferlen, M. Rueping, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 1999, 82, 2067-2093;
64. b)R. Frank, M. Jakob, F. Thunecke, G. Fischer, M. Schutkowski, Angew. Chem. 2000, 112, 1163-1165;
65. Angew. Chem. Int. Ed. 2000, 39, 1120-1122.
66. X M. Hynes, J. Chem. Soc. Dalton Trans. 1993, 311-312.
67. P. R. Mitchell, H. Sigel, Eur. J. Biochem. 1978, 88, 149-154.
68. T. H. Lilley, H. Linsdell, A. Maestre, J. Chem. Soc. Faraday Trans. 1992, 55, 2865-2870.