Group 3 metal complexes supported by tridentate pyridine- and thiophene-linked bis(naphtholate) ligands: Synthesis, structure, and use in stereoselective ring-opening polymerization of racemic lactide and β-butyrolactone

Dalton Transactions

Volumn 39, Issue 29, 2010, Pages 6739-6752

  Grunova, Ekaterina ^a   Kirillov, Evgueni ^a   Roisnel, Thierry ^a   Carpentier, Jean Franois ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDO COMPLEXES; ATACTIC POLYMERS; BUTYROLACTONES; CALCULATED VALUES; DONOR LIGANDS; HIGH YIELD; LACTIDES; METAL CENTERS; POLY(3-HYDROXYBUTYRATE); POLY(LACTIDES); SILYL SUBSTITUENTS; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID-STATE STRUCTURES; STEREO-SELECTIVE; STEREOCONTROL; SYNDIOTACTICS;

CHELATION; LANTHANUM; LIGANDS; METAL COMPLEXES; ORGANIC POLYMERS; POLYDISPERSITY; POLYMERS; PYRIDINE; RING OPENING POLYMERIZATION; SCANDIUM; SCANDIUM COMPOUNDS; SYNTHESIS (CHEMICAL); THIOPHENE; TOLUENE; X RAY DIFFRACTION; YTTRIUM;

ORGANIC SOLVENTS;

EID: 77954701081     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/b920283h     Document Type: Article

References (116)

1. D. C. Bradley, R. M. Mehrotra, I. P. Rothwell, A. Singh Alkoxo and Aryloxo Derivatives of Metals, Academic Press, London, 2001
2. R. M. Mehrotra A. Singh Prog. Inorg. Chem. 1997 46 239
3. R. C. Mehrotra A. Singh U. M. Triptathi Chem. Rev. 1991 91 1287
4. J. Tian G. W. Coates Angew. Chem., Int. Ed. 2000 39 3626
5. P. D. Hustad J. Tian G. W. Coates J. Am. Chem. Soc. 2002 124 3614
6. S. Reinartz A. F. Mason E. B. Lobkovsky G. W. Coates Organometallics 2003 22 2542
7. A. F. Mason G. W. Coates J. Am. Chem. Soc. 2004 126 10798
8. A. F. Mason G. W. Coates J. Am. Chem. Soc. 2004 126 16326
9. J. Saito M. Mitani J. Mohri Y. Yoshida S. Matsui S. Ishii S. Kojoh N. Kashiwa T. Fujita Angew. Chem., Int. Ed. 2001 40 2918
10. S. Matsui M. Mitani J. Saito Y. Tohi H. Makio N. Matsukawa Y. Takagi K. Tsuru M. Nitabaru T. Nakano H. Tanaka N. Kashiwa T. Fujita J. Am. Chem. Soc. 2001 123 6847
11. T. Matsugi F. Fujita Chem. Soc. Rev. 2008 37 1264
12. R. M. Gauvin J. A. Osborn J. Kress Organometallics 2000 19 2944
13. K. Takaoki T. Miyatake Macromol. Symp. 2000 157 251
14. Y. Nakayama K. Watanabe N. Ueyama A. Nakamura A. Harada J. Okuda Organometallics 2000 19 2498
15. M. C. W. Chan K. H. Tam Y. L. Pui N. Y. Zhu J. Chem. Soc., Dalton Trans. 2002 3085
16. M. C. W. Chan K. H. Tam N. Y. Zhu P. Chiu S. Matsui Organometallics 2006 25 785
17. T. Agapie L. M. Henling A. G. DiPasquale A. L. Rheingold J. E. Bercaw Organometallics 2008 27 6245
18. E. Y. Tshuva I. Goldberg M. Kol H. Weitman Z. Goldschmidt Chem. Commun. 2000 379
19. E. Y. Tshuva I. Goldberg M. Kol J. Am. Chem. Soc. 2000 122 10706
20. E. Y. Tshuva I. Goldberg M. Kol Z. Goldschmidt Chem. Commun. 2001 2120
21. E. Y. Tshuva I. Goldberg M. Kol J. Am. Chem. Soc. 2001 123 3621
22. E. Y. Tshuva I. Goldberg M. Kol Z. Goldschmidt Organometallics 2001 20 3017
23. E. Y. Tshuva S. Groysman I. Goldberg M. Kol Z. Goldschmidt Organometallics 2002 21 662
24. S. Groysman E. Y. Tshuva I. Goldberg M. Kol Z. Goldschmidt M. Shuster Organometallics 2004 23 5291
25. S. Segal I. Goldberg M. Kol Organometallics 2005 24 200
26. C. Capacchione A. Proto H. Ebeling R. Mulhaupt K. Moller T. P. Spaniol J. Okuda J. Am. Chem. Soc. 2003 125 4964
27. C. Capacchione F. De Carlo C. Zannoni J. Okuda A. Proto Macromolecules 2004 37 8918
28. B. Lian T. P. Spaniol J. Okuda Organometallics 2007 26 6653
29. G. J. M. Meppelder K. Beckerle R. Manivannan J. Okuda Chem.-Asian J. 2008 3 1312
30. G. J. P. Britovsek V. C. Gibson D. F. Wass Angew. Chem., Int. Ed. 1999 38 428
31. G. W. Coates P. D. Hustad S. Reinartz Angew. Chem., Int. Ed. 2002 41 2236
32. F. T. Edelmann D. M. M. Freckmann H. Schumann Chem. Rev. 2002 102 1851
33. V. C. Gibson S. K. Spitzmesser Chem. Rev. 2003 103 283
34. J. Gromada A. Mortreux J.-F. Carpentier Coord. Chem. Rev. 2004 248 397
35. P. Corradini G. Guerra L. Cavallo Acc. Chem. Res. 2004 37 231
36. M. Kol, S. Segal, S. Groysman in Stereoselective Polymerization with Single-Site Catalysts, CRC Press LLC, Boca Raton, Fla, 2008, pp. 345-361
37. J. Okuda Stud. Surf. Sci. Catal. 2007 172 11
38. G. J. Domski J. M. Rose G. W. Coates A. D. Bolig M. Brookhart Prog. Polym. Sci. 2007 32 30
39. O. Dechy-Cabaret B. Martin-Vaca D. Bourissou Chem. Rev. 2004 104 6147
40. B. J. O'Keefe M. A. Hillmyer W. B. Tolman J. Chem. Soc., Dalton Trans. 2001 2215
41. J. Wu T.-L. Yu C.-T. Chen C.-C. Lin Coord. Chem. Rev. 2006 250 602
42. A. Amgoune C. M. Thomas J.-F. Carpentier Pure Appl. Chem. 2007 79 2013
43. R. H. Platel L. M. Hodgson C. K. Williams Polym. Rev. 2008 48 11
44. A. P. Dove Chem. Commun. 2008 6446
45. C.-X. Cai L. Toupet J.-F. Carpentier J. Organomet. Chem. 2003 683 131
46. C.-X. Cai A. Amgoune C. W. Lehmann J.-F. Carpentier Chem. Commun. 2004 330
47. A. Amgoune C. M. Thomas T. Roisnel J.-F. Carpentier Chem.-Eur. J. 2006 12 169
48. A. Amgoune C. M. Thomas S. Ilinca T. Roisnel J.-F. Carpentier Angew. Chem., Int. Ed. 2006 45 2782
49. A. Amgoune C.M. Thomas J.-F. Carpentier Macromol. Rapid Commun. 2007 28 693
50. N. Ajellal M. Bouyahyi A. Amgoune C. M. Thomas A. Bondon I. Pillin Y. Grohens J.-F. Carpentier Macromolecules 2009 42 987
51. H. Ma T. P. Spaniol J. Okuda Dalton Trans. 2003 4770
52. H. Y. Ma J. Okuda Macromolecules 2005 38 2665
53. H. Y. Ma T. P. Spaniol J. Okuda Angew. Chem., Int. Ed. 2006 45 7818
54. H. Ma T. P. Spaniol J. Okuda Inorg. Chem. 2008 47 3328
55. F. Bonnet A. R. Cowley P. Mountford Inorg. Chem. 2005 44 9046
56. X. Liu X. Shang T. Tang N. Hu F. Pei D. Cui X. Chen X. Jing Organometallics 2007 26 2747
57. P. I. Binda E. E. Delbridge Dalton Trans. 2007 4685
58. Y. Takashima Y. Nakayama K. Watanabe T. Itono N. Ueyama A. Nakamura H. Yasuda A. Harada J. Okuda Macromolecules 2002 35 7538
59. Y. Sarazin R. Howard D. Hughes S. Humphrey M. Bochmann Dalton Trans. 2006 340
60. S. Gendler S. Segal I. Goldberg Z. Goldschmidt M. Kol Inorg. Chem. 2006 45 4783
61. A. J. Chmura M. G. Davidson M. D. Jones M. D. Lunn M. F. Mahon A. F. Johnson P. Khunkamchoo S. L. Roberts S. S. F. Wong Macromolecules 2006 39 7250
62. A. J. Chmura M. G. Davidson C. J. Frankis M. D. Jones M. D. Lunn Chem. Commun. 2008 1293
63. S. Steinhauser U. Heinz J. Sander K. Hegetschweiler Z. Anorg. Allg. Chem. 2004 630 1829
64. Y. Q. Li Y. Liu W. M. Bu J. H. Guo Y. Wang Chem. Commun. 2000 1551
65. E. Kirillov, J.-F. Carpentier and A. Razavi, Eur. Pat. Appl., 2008, 290, p. 410.3
66. E. Kirillov T. Roisnel A. Razavi J.-F. Carpentier Organometallics 2009 28 5036
67. A. Le Borgne C. Pluta N. Spassky Macromol. Rapid Commun. 1994 15 955
68. N. Spassky V. Simic M. S. Montaudo L. G. Hubert-Pfalzgraf Macromol. Chem. Phys. 2000 201 2432
69. K. B. Aubrecht K. Chang M. A. Hillmyer W. B. Tolman J. Polym. Sci., Part A: Polym. Chem. 2001 39 284
70. G. R. Giesbrecht G. D. Whitener J. Arnold J. Chem. Soc., Dalton Trans. 2001 923
71. T. M. Ovitt G.W. Coates J. Am. Chem. Soc. 2002 124 1316
72. Y. Satoh N. Ikitake Y. Nakayama S. Okuno H. Yasuda J. Organomet. Chem. 2003 667 42
73. L. Zhang Z. Shen C. Yu L. Fan J. Macromol. Sci. Part A: Pure Appl. Chem. 2004 41 927
74. I. Westmoreland J. Arnold Dalton Trans. 2006 4155
75. A. Alaaeddine A. Amgoune C. M. Thomas S. Dagorne S. Bellemin-Laponnaz J.-F. Carpentier Eur. J. Inorg. Chem. 2006 3652
76. J. Wang T. Cai Y. Yao Q. Shen Dalton Trans. 2007 5275
77. S. Wang S. Wang S. Zhou G. Yang W. Luo N. Hu Z. Zhou H.-B. Song J. Organomet. Chem. 2007 692 2099
78. S. Zhou S. Wang E. Sheng L. Zhang Z. Yu X. Xi G. Chen W. Luo Y. Li Eur. J. Inorg. Chem. 2007 1519
79. H. Zhou H. Guo Y. Yao L. Zhou H. Sun H. Sheng Y. Zhang Q. Shen Inorg. Chem. 2007 46 958
80. M. T. Gamer P. W. Roesky I. Pallard M. Le Hellaye S. M. Guillaume Organometallics 2007 26 651
81. E. E. Delbridge D. T. Dugah C. R. Nelson B. W. Skelton A. H. White Dalton Trans. 2007 143
82. G. G. Skvortsov M. V. Yakovenko P. M. Castro G. K. Fukin A. V. Cherkasov J.-F. Carpentier A. A. Trifonov Eur. J. Inorg. Chem. 2007 3260
83. R. Heck E. Schulz J. Collin J.-F. Carpentier J. Mol. Catal. A: Chem. 2007 268 163
84. N. Ajellal D. M. Lyubov M. A. Sinenkov G. K. Fukin A. V. Cherkasov C. M. Thomas J.-F. Carpentier A. A. Trifonov Chem.-Eur. J. 2008 14 5440
85. T. V. Mahrova G. K. Fukin A. V. Cherkasov A. A. Trifonov N. Ajellal J.-F. Carpentier Inorg. Chem. 2009 48 4258
86. R. Anwander O. Runte J. Eppinger G. Gerstberger E. Herdtweck M. Spiegler J. Chem. Soc., Dalton Trans. 1998 847
87. J. Eppinger M. Speigler W. Hieringer W. A. Herrmann R. Anwander J. Am. Chem. Soc. 2000 122 3080
88. A. Alaaeddine C. M. Thomas T. Roisnel J.-F. Carpentier Organometallics 2009 28 1469
89. R. D. Shannon Acta Crystallogr., Sect. A: Cryst. Phys., Diffr., Theor. Gen. Crystallogr. 1976 A32 751
90. T. Agapie M. W. Day J. E. Bercaw Organometallics 2008 27 6123
91. P. N. O'Shaughnessy P. D. Knight C. Morton K. M. Gillespie P. Scott Chem. Commun. 2003 1770
92. D. V. Gribkov K. C. Hultzsch F. Hampel Chem.-Eur. J. 2003 9 4796
93. L. Lavanant T.-Y. Chou Y. Chi C. W. Lehmann L. Toupet J.-F. Carpentier Organometallics 2004 23 5450
94. E. Grunova E. Kirillov T. Roisnel J.-F. Carpentier Organometallics 2008 27 5691
95. C. Runschke G. Meyer Z. Anorg. Allg. Chem. 1997 623 1493
96. Y. Li F.-K. Zheng X. Liu W.-Q. Zou G.-C. Guo C.-Z. Lu J.-S. Huang Inorg. Chem. 2006 45 6308
97. L. Natrajan J. Pecaut M. Mazzanti Dalton Trans. 2006 1002
98. I. Barakat P. Dubois R. Jerome P. Teyssie J. Polym. Sci., Part A: Polym. Chem. 1993 31 505 514
99. Y. Watanabe T. Aida S. Inoue Macromolecules 1990 23 2612
100. M. Helou O. Miserque J.-M. Brusson J.-F. Carpentier S. M. Guillaume Chem.-Eur. J. 2008 14 8772
101. V. Poirier T. Roisnel J.-F. Carpentier Y. Sarazin Dalton Trans. 2009 9820
102. K. A. M. Thakur R. T. Kean E. S. Hall J. J. Kolstad T. A. Lindgren M. A. Doscotch J. I. Siepmann E. J. Munson Macromolecules 1997 30 2422
103. K. A. M. Thakur R. T. Kean E. S. Hall J. J. Kolstad E. J. Munson Macromolecules 1998 31 1487
104. K. A. M. Thakur R. T. Kean M. T. Zell B. E. Padden E. J. Munson Chem. Commun. 1998 1913
105. M. H. Chisholm S. S. Iyer D. G. McCollum M. Pagel U. Werner-Zwanziger Macromolecules 1999 32 963
106. A. Altomare M. C. Burla M. Camalli G. Cascarano C. Giacovazzo A. Guagliardi A. G. G. Moliterni G. Polidori R. Spagna J. Appl. Crystallogr. 1999 32 115
107. G. M. Sheldrick SHELXS-97, Program for the Determination of Crystal Structures, University of Goettingen (Germany), 1997
108. G. M. Sheldrick SHELXL-97, Program for the Refinement of Crystal Structures, University of Goettingen (Germany), 1997
109. L. J. Farrugia J. Appl. Crystallogr. 1999 32 837
110. P. Van Der Sluis A. L. Spek Acta Crystallogr., Sect. A: Found. Crystallogr. 1990 A46 194
111. Spek A.L., Acta Crystallogr., 1990, 46, 34.
112. The following atom numbering of the naphtholate unit is used.
113. 3H2 with the tris(amido) precursor were investigated instead of isolated compounds.We independently checked for 2 and 3 that the corresponding in situ systems lead to similar polymerization results.
114. 13C NMR spectroscopy, comparing the experimental triad/tetrad resonance intensities with those calculated from a Bernoullian statistics, gave results consistent with a chain-end stereocontrol mechanism. For instance, Table 3, entry 5 (resonance, experimental/calculated): rmr, 0.35/0.39; rmm/mmr, 0.07/0.05; mmr/rmm, 0.08/0.05; mrm+mmm, 0.50/0.44+0.07.
115. n values must be done with caution since the latter values are uncorrected and might be overestimated. However, no reliable correction factor accounting for the difference in hydrodynamic radius between PHBs and polystyrene standards has been reported to our knowledge. SEC analysis of higher molecular weight PHBs is known to be problematic. See reference 7f and references cited therein.
116. A. L. Spek Acta Crystallogr. 1990 A46 C-34