Monomer versus alcohol activation in the 4-dimethylaminopyridine-catalyzed ring-opening polymerization of lactide and lactic O-carboxylic anhydride

Chemistry - A European Journal

Volumn 14, Issue 17, 2008, Pages 5304-5312

  Bonduelle, Colin ^a   Martín Vaca, Blanca ^a   Cossío, Fernando P ^b   Bourissou, Didier ^a  

^a UMR 5069) 118 route de Narbonne   (France)

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

Author keywords

Density functional calculations; Dimethylaminopyridine; Hydrogen bonds; Organocatalysis; Ring opening polymerization

Indexed keywords

ABS RESINS; ACIDS; CHEMICAL REACTIONS; DICHLOROMETHANE; HYDROGEN; HYDROGEN BONDS; MECHANISMS; MONOMERS; ORGANIC POLYMERS; POLYMERIZATION; POLYMERS;

4-DIMETHYLAMINOPYRIDINE; ACETIC ANHYDRIDE; B3LYP/6-31G; BASIC NITROGEN; BI-FUNCTIONAL CATALYSTS; CARBOXYLIC ANHYDRIDE; DENSITY FUNCTIONAL CALCULATIONS; DIMETHYLAMINOPYRIDINE; HYDROGEN ATOMS; HYDROGEN BONDINGS; LACTIDE; MODEL REACTIONS; NUCLEOPHILIC ACTIVATION; ORGANOCATALYSIS; RING-OPENING; SINGLE-POINT CALCULATIONS; SOLVENT EFFECTS; STEPWISE MECHANISM; TETRAHEDRAL INTERMEDIATES;

RING OPENING POLYMERIZATION;

4 AMINOPYRIDINE; 4 DIMETHYLAMINOPYRIDINE; 4-DIMETHYLAMINOPYRIDINE; ALCOHOL DERIVATIVE; DILACTIDE; DIOXANE DERIVATIVE; DRUG DERIVATIVE; LACTIC ACID DERIVATIVE; LACTIC ACID ETHYL ESTER; LACTIC O CARBOXYLIC ANHYDRIDE; LACTIC O-CARBOXYLIC ANHYDRIDE; METHANOL; POLYMER;

ARTICLE; CATALYSIS; CHEMISTRY;

4-AMINOPYRIDINE; ALCOHOLS; CATALYSIS; DIOXANES; LACTATES; METHANOL; POLYMERS;

EID: 53849101052     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800346     Document Type: Article

References (105)

1. For general reviews of the applications of PLAs, see: a) J. Lunt, Polym. Degrad. Stab. 1998, 59, 145-152;
2. b) W. Amass, A. Amass, B. Tighe, Polym. Int. 1998, 47, 89-144;
3. c) R. E. Drumright, P. R. Gruber, D.E. Henton, Adv. Mater. 2000, 12, 1841-1846;
4. d) J. C. Middleton, A. J. Tipton, Biomaterials 2000, 21, 2335-2346;
5. e) A. Sodergard, M. Stolt, Prog. Polym. Sci. 2002, 27, 1123-1163;
6. f) A.C. Albertsson, I. K. Varma. Biomacromolecules 2003, 4, 1466-1486;
7. g) R. Auras, B. Harte, S. Selke, Macromol. Biosci. 2004, 4, 835-864;
8. h) S. Mecking, Angew. Chem. 2004, 116, 1096-1104;
9. Angew. Chem. Int. Ed. 2004, 43, 1078-1085;
10. i) C. K. Williams, Chem. Soc. Rev. 2001, 36, 1573-1580.
11. For recent reviews, see: a) A. P. Dove, R. C. Pratt, B. G. G. Lohmeijer, H. Li, E. C. Hagberg, R. M. Waymouth, J. L. Hedrick in N-Heterocyclic Carbenes in Synthesis (Ed.: S. P. Nolan), Wiley-VCH, Weinheim, 2006, pp. 275-296;
12. b) D. Bourissou, S. Moebs-Sanchez, B. Martin-Vaca, C. R. Chim. 2007, 10, 775-794;
13. c) N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. G Lohmeijer, J. L. Hedrick. Chem. Rev. 2007, 107, 5813-5840.
14. F. Nederberg, E. F. Connor, M. Möller, T. Glauser, J. L. Hedrick, Angew. Chem. 2001, 113, 2784-2787;
15. Angew. Chem. Int. Ed. 2001, 40, 2712-2715.
16. a) G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602-615;
17. Angew. Chem. Int. Ed. Engl. 1978, 17, 569-583:
18. b) A. Hassner, L. R. Krepski, V. Alexanian, Tetrahedron 1978, 34, 2069-2076:
19. c) E. F. V. Scriven, Chem. Soc. Rev. 1983, 12, 129-161;
20. d) C. Grondai, Synlett 2003, 10, 1568-1569:
21. e) M. R. Heinrich, H. S. Klisa, H. Mayr, W. Steglich, H. Zipse, Angew. Chem. 2003, 115, 4975-4977:
22. Angew. Chem. Int. Ed. 2003, 42, 4826-4828;
23. f) A. C. Spivey, S. Arseniyadis, Angew. Chem. 2004, 116, 5552-5557:
24. Angew. Chem. Int. Ed. 2004, 43, 5436-5441:
25. g) C. B. Fischer, S. Xu, H. Zipse, Chem. Eur. J. 2006, 12, 5779-5784;
26. h) A. Sakakura, K. Kawajiri, T. Ohkubo, Y. Kosugi, K. Ishihara, J. Am. Chem. Soc. 2007, 129, 14775-14779.
27. a) E. F. Connor, G. W. Nyce, M. Myers, A. Möck, J. L. Hedrick, J. Am. Chem. Soc. 2002, 124, 914-915;
28. b) G. W. Nyce, J. A. Lamboy, E. F. Connor, R. M. Waymouth, J. L. Hedrick, Org. Lett. 2002, 4, 3587-3590:
29. c) G. W. Nyce, T. Glauser, E. F. Connor, A. Möck, R. M. Waymouth, J. L. Hedrick, J. Am. Chem. Soc 2003, 125, 3046-3056:
30. d) G. W. Nyce, S. Csihony, R. M. Waymouth, J. L. Hedrick, Chem. Eur. J. 2004, 111, 4073-4079;
31. e) O. Coulembier, A. P. Dove, R. C. Pratt, A. C. Senlman, D. A. Culkin, L. Mespouille, P. Dubois, R. M. Waymouth, J. L. Hedrick, Angew. Chem. 2005, 117, 5044-5048;
32. Angew. Chem. Int. Ed. 2005, 44, 4964-4968:
33. f) S. Csihony, D. A. Culkin, A. C. Sentman, A. P. Dove, R. M. Waymouth, J. L. Hedrick, J. Am. Chem. Soc 2005, 127, 9079-9084:
34. g) A. P. Dove, H. Li, R. C. Pratt, B. G. G. Lohmeijer. D. A. Culkin, R. M. Waymouth, J. L. Hedrick, Chem. Commun. 2006, 2881-2883:
35. h) 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:
36. i) A. P. Dove, R. C. Prall, B. G. G. Lohmeijer, D. A. Culkin, E. C. Hagberg, G. W. Nyce, R. M. Waymouth, J. L. Hedrick, Polymer 2006, 47, 4018-4025;
37. j) D. A. Culkin, W. Jeong, S. Csihony, E. D. Gomez, N. P. Balsara, J. L. Hedrick, R. M. Waymouth, Angew. Chem. 2007, 119, 2681-2684;
38. Angew. Chem. Int. Ed. 2007, 46, 2627-2630;
39. k) O. Coulembier, M. K. Kiesewetter, A. Mason, P. Dubois, J. L. Hedrick, R. M. Waymouth, Angew. Chem. 2007, 119, 4803-4805;
40. Angew. Chem. Int. Ed. 2007, 46, 4719-4721.
41. D. Bourissou, B. Martín-Vaca, A. Dumitrescu, M. Graullier, F. Lacombe. Macromolecules 2005, 38, 9993-9998.
42. 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;
43. b) R. C. Pratt, B. G. G. Lohmeijer, D. A. Long, P. N. Pontus Lundberg, A. P. Dove, H. Li, C. G. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 59, 7863-7871.
44. 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;
45. b) B. G. G. Lohmeijer, R. C. Pratt, F. Leibfarth, J. W. Logan, D. A. Long, A. P. Dove, F. Nederberg, J. Choi, C. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 8574-8583.
46. a) L. Zhang, F. Nederberg, J. M. Messman, R. C. Pratt, J. L. Hedrick, C.G. Wade, J. Am. Chem. Soc. 2007, 129, 12610-12611;
47. b) L. Zhang, F. Nederberg, R. C. Pratt, R. M. Waymouth, J. L. Hedrick, C. G. Wade, Macromolecules 2007, 40, 4154-4158.
48. a) B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, J. Chem. Soc. Dalton Trans. 2001, 2215-2224;
49. b) O. Dechy-Cabaret, B. Martín-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147-6176;
50. c) J. Wu, T. Yu, C. Chen, C. Lin, Coord. Chem. Rev. 2005, 250, 602-626.
51. For theoretical studies on the ROP of lactide promoted by aluminum and stannous complexes, see: a) J. L. Eguiburu, J. Fernandez-Berridi, F. P. Cossío, J. San Roman, Macromolecules 1999, 32, 8252-8258;
52. b) M. Ryner, K. Stridsberg, A. C. Albertsson, H. Von Schenck, M. Svensson, Macromolecules 2001, 34, 3877-3881;
53. c) H. von Schenck, M. Ryner, A. C. Albertsson, M. Svensson, Macromolecules 2002, 35, 1556-1562.
54. a) C. Lai, H. M. Lee, C. Hu, Tetrahedron Lett. 2005, 46, 6265-6270; for experimental mechanistic studies, see also:
55. b) S. Csihony, G. W. Nyce, A. C. Sentman, R. M. Waymouth, J. L Hedrick, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2004, 45, 319-320:
56. c) M. Movassaghi, M. A. Schmidt, Org. Lett. 2005, 7, 2453-2456.
57. L. Simon, J. M. Goodman, J. Org. Chem. 2007, 72, 9656-9662.
58. S. Xu, I. Held, B. Kempf, H. Mayr, W. Steglich, H. Zipse, Chem. Eur. J. 2005, 11, 4751-4757.
59. a) O. Thillaye du Boullay, E. Marchai, B. Martín-Vaca, F. P. Cossío, D. Bourissou, J. Am. Chem. Soc 2006, 128, 16442-16443;
60. b) O. Thillaye du Boullay, C. Bonduelle, B. Martín-Vaca, D. Bourissou, Chem. Commun. 2008, 1786-1788.
61. For early studies on the ROP of O-carboxylic anhydrides, see: a) I. J. Smith, B. J. Tighe, Makromol. Chem. 1981, 182, 313-324;
62. b) H. R. Kricheldorf, J. M. Jonté, Polym. Bulletin 1983, 9, 276-281.
63. See the Supporting Information for details.
64. -1 in 1,4-dioxane; see: A. Duda, S. Penczek, Macromolecules 1990, 23, 1636-1639.
65. orthoNCO between the pyridinium ring and C=O skeleton range from 3 to 19°; see: a) C. Lohse, S. Hollenstein, T. Laube, Angew. Chem. 1991, 103, 1679;
66. Angew. Chem. Int. Ed. Engl. 1991, 30, 1658;
67. b) G. L. Bryant, J. A. King, Acta Crystallogr. Sect. C 1992, 48, 2036-2039.
68. For general reviews on nonclassical O⋯H-C hydrogen bonding, see: a) G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296;
69. b) G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449;
70. c) T. Steiner, Chem. Commun. 1997, 727-734;
71. d) T. Steiner, C.R. Desiraju, Chem. Commun. 1998, 891-892;
72. e) T. Steiner, Angew. Chem. 2002, 114, 50-80;
73. Angew. Chem. Int. Ed. 2002, 41, 48-76;
74. f) G. R. Desiraju, Chem. Commun. 2005, 2995-3001.
75. The activation of carbonyl compounds towards hetero-Diels-Alder reactions through nonclassical hydrogen-bonding interactions has recently been substantiated both experimentally and theoretically; see: a) Y. Huang, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 9662-9663;
76. b) L. R. Domingo, J. Andrés, J. Org. Chem. 2003, 68, 8662-8668;
77. c) V. Polo, L. R. Domingo, J. Andrés, J. Phys. Chem. A 2005, 109, 10438-10444.
78. The terms "basic route" and "base-catalyzed mechanism" refer to the ability of DMAP to activate the initialing/propagating alcohol through N⋯H-O hydrogen bonding and to transfer the labile proton back to the exocyclic oxygen atom of the monomer.
79. A. Williams, Acc. Chem. Res. 1989, 22, 387-392.
80. For experimental and computational studies on the hydrolysis and alcoholysis of carboxylic esters and formates, see: a) S. Ba-Saif, A. K. Luthra, A. Williams, J. Am. Chem. Soc. 1987, 109, 6362-6368;
81. b) S. Ba-Saif, A. K. Luthra, A. Williams, J. Am. Chem. Soc. 1989, 111, 2647-2652:
82. c) J. P. Guthrie, J. Am. Chem. Soc. 1991, 113, 3941 -3949;
83. d) A. Hengge, J. Am. Chem. Soc. 1992, 114, 6575-6576:
84. e) J. F. Marlier, J. Am. Chem. Soc. 1993, 115, 5953-5956:
85. f) G.O. Andres, A. B. Pierini, R. H. de Rossi, J. Org. Chem. 2006, 71, 7650-7656.
86. For experimental and theoretical studies on the aminolysis of carboxylic esters and formates, see: a) T Oie, G. H. Loew, S. K. Burt, J. S. Binkley, R. D. MacElroy, J. Am. Chem. Soc. 1982, 104, 6169-6174:
87. b) L. Wang, H. Zipse, Liebigs Ann. 1996, 1501-1510;
88. c) L. Wang, H. Zipse, Liebigs Ann. 1996, 1511-1522;
89. d) W. Yang, D.O. Drueckhammer, Org. Lett. 2000, 2, 4133-4136;
90. e) S. Ilieva, B. Galabov, D. G. Musaev, K. Morokuma, H. F. Schaefer, J. Org. Chem. 2003, 68, 1496-1502;
91. f) B. Galabov, Y. Atanasov, S. Ilieva, H. F. Schaefer, J. Phys. Chem. A 2005, 109, 11470-11474.
92. α-Lactones are elusive intermediates: see: a) G. L'abbé, Angew. Chem. 1980, 92, 277-290;
93. Angew. Chem. Int. Ed. Engl. 1980, 19, 276-289;
94. b) C. F. Rodriquez. I. H. Williams, J. Chem. Soc. Perkin Trans. 2 1997, 953-957;
95. c) C. F. Rodriquez, I. H. Williams, J. Chem. Soc. Perkin Trans. 2 1997, 959-965;
96. d) J. G. Buchanan, M. H. Charlton, M. F. Mahon, J.J. Robinson, G. D. Ruggiero, I. H. Williams, J. Phys. Org. Chem. 2002, 15, 642-646.
97. Monoesters of carbonic acids are known to be highly unstable with respect to decarboxylation; see: A. Dibenedetto. M. Aresta, P. Giannoccaro, C. Pastore, I. Pápai, G. Schubert, Eur. J. Inorg. Chem. 2006, 908-913.
98. -1 higher in energy than II′1).
99. a) R. G. Parr, W. Yang, Functional Theory of Atoms and Molecules (Eds: R. Breslow, J. B. Goodenough), Oxford University Press, New York, 1989:
100. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652:
101. c) C. Lee, W. Yang, R. G. Parr, Phys Rev. 1988, B37, 785-789.
102. Gaussian 03, Revision B.05, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A.D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.
103. a) C. Gonzalez, H. B. Schlegel, J. Chem. Phys 1989, 90, 2154-2561:
104. b) C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527.
105. M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43-54.