Discrete cationic zinc and magnesium complexes for dual organic/organometallic-catalyzed ring-opening polymerization of trimethylene carbonate

Chemistry - A European Journal

Volumn 18, Issue 30, 2012, Pages 9360-9370

  Brignou, Pierre ^a   Guillaume, Sophie M ^a   Roisnel, Thierry ^a   Bourissou, Didier ^b   Carpentier, Jean François ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

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

Author keywords

cationic complexes; dual catalyst; magnesium; ring opening polymerization; zinc

Indexed keywords

BENZYL ALCOHOL; CATALYST SYSTEM; CATALYTIC SYSTEM; CATIONIC COMPLEXES; CATIONIC METALS; HIGH ACTIVITY; ION PAIRS; LEWIS ACIDIC; MAGNESIUM COMPLEXES; NEUTRAL COMPLEXES; NEUTRAL COMPOUNDS; NUCLEOPHILICITIES; TERTIARY AMINE; TOLUENE SOLUTION; TRIMETHYLENE CARBONATE; TURNOVER FREQUENCY; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

BIOGRAPHIES; CARBONATION; CATALYSTS; IONS; MAGNESIUM; METAL COMPLEXES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; PHENOLS; TOLUENE; X RAY CRYSTALLOGRAPHY; ZINC;

POLYMERIZATION;

EID: 84863953421     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200336     Document Type: Article

References (97)

1. P. Dubois, O. Coulembier, J.-M. Raquez, (Eds.), Handbook of Ring-Opening Polymerization, Wiley-VCH, Weinheim, 2009.
2. B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, Dalton Trans. 2001, 2215-2224
3. O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147-6176
4. C. M. Thomas, Chem. Soc. Rev. 2010, 39, 165-173
5. M. J. Stanford, A. P. Dove, Chem. Soc. Rev. 2010, 39, 486-494
6. J.-F. Carpentier, Macromol. Rapid Commun. 2010, 31, 1696-1705.
7. For leading reviews, see
8. N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. Lohmeijer, J. L. Hedrick, Chem. Rev. 2007, 107, 5813-5840
9. D. Bourissou, S. Moebs-Sanchez, B. Martin-Vaca, C. R. Chim. 2007, 10, 775-794
10. M. K. Kiesewetter, E. J. Shin, J. L. Hedrick, R. M. Waymouth, Macromolecules 2010, 43, 2093-2107.
11. K. E. Uhrich, S. M. Cannizzaro, R. S. Langer, K. M. Shakesheff, Chem. Rev. 1999, 99, 3181-3198
12. R. E. Drumright, P. R. Gruber, D. E. Henton, Adv. Mater. 2000, 12, 1841-1846.
13. G. Rokicki, Prog. Polym. Sci. 2000, 25, 259-342
14. A.-C. Albertsson, I. K. Varma, Biomacromolecules 2003, 4, 1466-1486
15. M. Vert, Biomacromolecules 2005, 6, 538-546
16. B. D. Ulery, L. S. Nair, C. T. Laurencin, J. Polym. Sci. Part B: Polym. Phys. 2011, 49, 832-864
17. T. Artham, M. Doble, Macromol. Biosci. 2008, 8, 14-24
18. J. Feng, R.-X. Zhuo, X.-Z. Zhang, Prog. Polym. Sci. 2012, 37, 211-236
19. H. Tian, Z. Tang, X. Zhuang, X. Chen, Prog. Polym. Sci. 2012, 37, 237-280
20. F. Suriano, O. Coulembier, J. L. Hedrick, P. Dubois, Polym. Chem. 2011, 2, 528-533.
21. C.-H. Zhou, J. N. Beltramini, Y.-X. Fan, G. Q. Lu, Chem. Soc. Rev. 2008, 37, 527-549
22. A. Behr, J. Eilting, K. Irawadi, J. Leschinski, F. Lindner, Green Chem. 2008, 10, 13-30
23. A. Corma, S. Iborra, A. Velty, Chem. Rev. 2007, 107, 2411-2502
24. P. N. R. Vennestrøm, C. M. Osmundsen, C. H. Christensen, E. Taarning, Angew. Chem. Int. Ed. 2011, 50, 10502-10509
25. B. Katryniok, H. Kimura, E. Skrzyska, J.-S. Girardon, P. Fongarland, M. Capron, R. Ducoulombier, N. Mimura, S. Paul, F. Dumeignil, Green Chem. 2011, 13, 1960-1979.
26. M. Helou, O. Miserque, J.-M. Brusson, J.-F. Carpentier, S. M. Guillaume, Chem. Eur. J. 2010, 16, 13805-13813
27. J. Feng, X.-L. Wang, F. He, R.-X. Zhuo, Macromol. Rapid Commun. 2007, 28, 754-758
28. D. Delcroix, B. Martin-Vaca, D. Bourissou, C. Navarro, Macromolecules 2010, 43, 8828-8835.
29. For representative and leading references on zinc systems, see
30. X. Chen, S. P. McCarthy, R. A. Gross, Macromolecules 1997, 30, 3470-3476
31. K. J. Zhu, R. W. Hendren, K. Jensen, C. G. Pitt, Macromolecules 1991, 24, 1736-1740
32. E. J. Vandenberg, D. Tian, Macromolecules 1999, 32, 3613-3619
33. P. Dobrzynski, M. Pastusiak, M. Bero, J. Polym. Sci. 2005, 43, 1913-1922
34. H. R. Kricheldorf, J. Jenssen, I. Kreiser-Saunders, Makromol. Chem. 1991, 192, 2391-2399
35. C. Zhang, L. Liao, S. Gong, J. Appl. Polym. Sci. 2008, 110, 1236-1241
36. M. Le Hellaye, N. Fortin, J. Guilloteau, A. Soum, S. Lecommandoux, S. M. Guillaume, Biomacromolecules 2008, 9, 1924-1933
37. I. Palard, M. Schappacher, B. Belloncle, A. Soum, S. M. Guillaume, Chem. Eur. J. 2007, 13, 1511-1521
38. M. Helou, O. Miserque, J.-M. Brusson, J.-F. Carpentier, S. M. Guillaume, Chem. Eur. J. 2008, 14, 8772-8775
39. M. Helou, O. Miserque, J.-M. Brusson, J.-F. Carpentier, S. M. Guillaume, Adv. Synth. Catal. 2009, 351, 1312-1324
40. M. Helou, O. Miserque, J.-M. Brusson, J.-F. Carpentier, S. M. Guillaume, Macromol. Rapid Commun. 2009, 30, 2128-2135
41. M. Helou, O. Miserque, J.-M. Brusson, J.-F. Carpentier, S. M. Guillaume, ChemCatChem 2010, 2, 306-313
42. N. Ajellal, J.-F. Carpentier, C. Guillaume, S. M. Guillaume, M. Helou, V. Poirier, Y. Sarazin, A. Trifonov, Dalton Trans. 2010, 39, 8363-8376
43. S. M. Guillaume, J.-F. Carpentier, Catal. Sci. Technol. 2012, 2, 898-906.
44. For representative and leading references on alkaline-earth systems, see
45. D. J. Darensbourg, W. Choi, P. Ganguly, C. P. Richers, Macromolecules 2006, 39, 4374-4379
46. D. J. Darensbourg, W. Choi, O. Karroonnirun, N. Bhuvanesh, Macromolecules 2008, 41, 3493-3502
47. A. D. Schofield, M. L. Barros, M. G. Cushion, A. D. Schwarz, P. Mountford, Dalton Trans. 2009, 85-96
48. Z.-X. Wang, C.-Y. Qi, Organometallics 2007, 26, 2243-2251
49. L. F. Sanchez-Barba, A. Garcés, M. Fajardo, C. Alonso-Moreno, J. Fernandez-Baeza, A. Otero, A. Antinolo, J. Tejeda, A. Lara-Sanchez, M. I. Lopez-Solera, Organometallics 2007, 26, 6403-6411
50. L. F. Sanchez-Barba, D. L. Hughes, S. M. Humphrey, M. Bochmann, Organometallics 2006, 25, 1012-1020
51. T.-L. Yu, C.-C. Wu, C.-C. Chen, B.-H. Huang, J. Wu, C.-C. Lin, Polymer 2005, 46, 5909-5917
52. M.-L. Shueh, Y.-S. Wang, B.-H. Huang, C.-Y. Kuo, C.-C. Lin, Macromolecules 2004, 37, 5155-5162
53. M. H. Chisholm, N. W. Eilerts, J. C. Huffman, S. S. Iyer, M. Pacold, K. Phomphrai, J. Am. Chem. Soc. 2000, 122, 11845-11854.
54. For representative and leading references on tin and aluminum systems, see
55. H. R. Kricheldorf, A. Stricker, Z. Gomurashvili, Macromol. Chem. Phys. 2001, 202, 413-420
56. D. J. Darensbourg, P. Ganguly, D. Billodeaux, Macromolecules 2005, 38, 5406-5410
57. K. Nilsson, L. Mellin, F. Nederberg, T. Bowden, Macromolecules 2007, 40, 901-908
58. K. R. Carter, R. Richter, H. R. Kricheldorf, J. L. Hedrick, Macromolecules 1997, 30, 6074-6076
59. Z. Florjanczyk, A. Plichta, M. Sobczak, Polymer 2006, 47, 1081-1090
60. J. Yang, Y. Yu, Q. Li, Y. Li, A. Cao, J. Polym. Sci. Part A: Polym. Chem. 2005, 43, 373-384; rare-earth systems
61. S. Agarwal, M. Puchner, Eur. Polym. J. 2002, 38, 2365-2371
62. H. Sheng, L. Zhou, Y. Zhang, Y. Yao, Q. Shen, J. Polym. Sci. A: Polym. Chem. 2007, 45, 1210-1218.
63. M. D. Hannant, M. Schormann, M. Bochmann, J. Chem. Soc. Dalton Trans. 2002, 4071-4073
64. D. A. Walker, T. J. Woodman, M. Schormann, D. L. Hughes, M. Bochmann, Organometallics 2003, 22, 797-803
65. Y. Sarazin, M. Schormann, M. Bochmann, Organometallics 2004, 23, 3296-3302
66. B. Lian, C. M. Thomas, O. L. Casagrande, C. W. Lehmann, T. Roisnel, J.-F. Carpentier, Inorg. Chem. 2007, 46, 328-340
67. C. A. Wheaton, B. J. Ireland, P. G. Hayes, Organometallics 2009, 28, 1282-1285
68. J. Börner, U. Flörke, K. Huber, A. Döring, D. Kuckling, S. Herres-Pawlis, Chem. Eur. J. 2009, 15, 2362-2376
69. C. A. Wheaton, P. G. Hayes, Chem. Commun. 2010, 46, 8404-8406; cationic alkaline-earth systems
70. B. J. Ireland, C. A. Wheaton, P. G. Hayes, Organometallics 2010, 29, 1079-1084
71. Y. Sarazin, V. Poirier, T. Roisnel, J.-F. Carpentier, Eur. J. Inorg. Chem. 2010, 3423-3428
72. Y. Sarazin, B. Liu, T. Roisnel, L. Maron, J.-F. Carpentier, J. Am. Chem. Soc. 2011, 133, 9069-9087
73. M. G. Cushion, P. Mountford, Chem. Commun. 2011, 47, 2276-2278.
74. For a rare example of a cationic organometallic (zirconocene) derivative used in the ROP of a seven-membered cyclic carbonate, see:, M. Hakayawa, M. Mitani, T. Yamada, T. Mukaiyama, Macromol. Rapid Commun. 1996, 17, 865-870.
75. E. Piedra-Arroni, P. Brignou, A. Amgoune, S. M. Guillaume, J.-F. Carpentier, D. Bourissou, Chem. Commun. 2011, 47, 9828-9830.
76. C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999-3025
77. Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745-2755.
78. C. K. Williams, L. E. Breyfogle, S. K. Choi, W. Nam, V. G. Young, Jr., M. A. Hillmyer, W. B. Tolman, J. Am. Chem. Soc. 2003, 125, 11350-11359.
79. B. M. Chamberlain, M. Cheng, D. R. Moore, T. M. Ovitt, E. Lobkovsky, G. W. J. Coates, J. Am. Chem. Soc. 2001, 123, 3229-3238
80. L. R. Rieth, D. R. Moore, E. B. Lobkovsky, G. W. J. Coates, J. Am. Chem. Soc. 2002, 124, 15239-15248.
81. S. J. Lancaster, A. Rodriguez, A. Lara-Sanchez, M. D. Hannant, D. A. Walker, D. L. Hughes, M. Bochmann, Organometallics 2002, 21, 451-453
82. Y. Sarazin, D. L. Hughes, N. Kaltsoyannis, J. A. Wright, M. Bochmann, J. Am. Chem. Soc. 2007, 129, 881-894
83. Y. Sarazin, N. Kaltsoyannis, J. A. Wright, M. Bochmann, Organometallics 2007, 26, 1811-1815.
84. M. Bochmann, Coord. Chem. Rev. 2009, 253, 2000-2014.
85. A. D. Horton, J. De With, A. J. Van Der Linden, H. Van De Weg, Organometallics 1996, 15, 2672
86. S. J. Lancaster, A. J. Mountford, D. L. Hughes, M. Schormann, M. Bochmann, J. Organomet. Chem. 2003, 680, 193-205
87. W. E. Piers, Adv. Organomet. Chem. 2005, 52, 1
88. T. Beringhelli, D. Donghi, D. Maggioni, G. D'Alfonso, Coord. Chem. Rev. 2008, 252, 2292-2313.
89. D. C. Bradley, I. S. Harding, A. D. Keefe, M. Motevalli, D. H. Zheng, J. Chem. Soc. Dalton Trans. 1996, 3931-3936
90. L. H. Doerrer, M. L. H. Green, J. Chem. Soc. Dalton Trans. 1999, 4325-4329
91. T. Beringhelli, G. Maggioni, G. D'Alfonso, Organometallics 2001, 20, 4927-4938.
92. R. D. Shannon, Acta Crystallogr. A 1976, 32, 751-767.
93. (β-α)/60, where α and β are the angles associated with the axial and equatorial ligands; the Ï value ranges from 0 (perfectly square pyramidal) to 1 (perfectly trigonal bipyramidal); see:, A. W. Addison, T. N. Rao, J. Reedjik, L. Van Rijn, G. C. Verschoor, J. Chem. Soc. Dalton Trans. 1984, 1349.
94. S. C. Watson, J. F. Eastham, J. Organomet. Chem. 1967, 9, 165-167.
95. G. M. Sheldrick, SHELXS-97, Program for the Determination of Crystal Structures, University of Göttingen, Germany, 1997
96. G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen; Germany, 1997
97. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.