Yttrium complexes supported by linked bis(amide) ligand: Synthesis, structure, and catalytic activity in the ring-opening polymerization of cyclic esters

Inorganic Chemistry

Volumn 48, Issue 9, 2009, Pages 4258-4266

  Mahrova, Tatyana V ^a   Fukin, Georgy K ^a   Cherkasov, Anton V ^a   Trifonov, Alexander A ^a   Ajellal, Noureddine ^b   Carpentier, Jean Francois ^b  

^a G A RAZUVAEV INSTITUTE OF ORGANOMETALLIC CHEMISTRY   (Russian Federation)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; 1,3 BUTADIENE DERIVATIVE; 1,3-BUTADIENE; AMIDE; BETA BUTYROLACTONE; BETA-BUTYROLACTONE; DILACTIDE; DIOXANE DERIVATIVE; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; LIGAND; ORGANOMETALLIC COMPOUND; POLYMER; YTTRIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

4-BUTYROLACTONE; AMIDES; BUTADIENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DIOXANES; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; POLYMERS; YTTRIUM;

EID: 66149140258     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic802427f     Document Type: Article

References (60)

1. (a) Mecking, S. Angew. Chem., Int. Ed. 2004, 43, 1078-1085.
2. (b) Drumright, R. E.; Gruber, P. R.; Henton, D. E. Adv. Mater. 2000, 12, 1841-1846.
3. (c) Auras, R.; Harte, B.; Selke, S. Macromol. Biosci. 2004, 4, 835-864.
4. (d) Ha, C.-S.; Gardella, J. A. Chem. Rev. 2005,105, 4205-4232.
5. (a) O'Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. J. Chem. Soc., Dalton Trans. 2001, 2215-2224.
6. (b) Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147-6176.
7. (c) Dove, A. P. Chem. Commun. 2008, 6446-6470.
8. Amgoune, A.; Thomas, C. M.; Carpentier, J.-F. Pure Appl. Chem. 2007, 79, 2013-2030.
9. (a) Cai, C.-X.; Amgoune, A.; Lehmann, C. W.; Carpentier, J.-F. Chem. Commun. 2004, 330-331.
10. (b) Amgoune, A.; Thomas, C. M.; Roisnel, T.; Carpentier, J.-F. ChemsEur. J. 2006, 12, 169-179.
11. (c) Castro, P. M.; Zhao, G.; Amgoune, A.; Thomas, C. M.; Carpentier, J.-F. Chem. Commun. 2006, 4509-4511.
12. (d) Amgoune, A.; Thomas, C. M.; Ilinca, S.; Roisnel, T.; Carpentier, J.-F. Ansew. Chem., Int. Ed. 2006, 45, 2782-2784.
13. (e) Amgoune, A.; Thomas, C. M.; Carpentier, J.-F. Macromol. Rapid Commun. 2007, 28, 693-697.
14. (f) Ma, H.; Spaniol, T. P.; Okuda, J. Dalton Trans. 2003, 4770-4780.
15. (g) Ma, H.; Okuda, J. Macromolecules 2005, 38, 2665-2673.
16. (h) Ma, H.; Spaniol, T. P.; Okuda, J. Ansew. Chem., Int. Ed. 2006, 45, 7818-7821.
17. (i) Bonnet, F.; Cowley, A. R.; Mountford, P. Inors. Chem. 2005, 44, 9046-9055.
18. (j) Dyer, H. E.; Huijster, S.; Schwarz, A. D.; Wang, C.; Duchateau, R.; Mountford, P. Dalton Trans. 2008, 32-35.
19. (k) Liu, X.; Chang, X.; Tang, T.; Hu, N.; Pei, F.; Cui, D.; Chen, X.; Jing, X. Orsanome- tallics 2007, 26, 2747-2757.
20. (a) Platel, R. P.; Hodgson, L. M.; White, A. J. P.; Williams, C. K. Orsanometallics 2007, 26, 4955-4969.
21. (b) Carver, C. T.; Monreal, M. J.; Diaconescu, P. L. Orsanometallics 2008, 27, 363-370.
22. (c) Cloke, F. G. N.; Elvidge, B. R.; Hitchcock, P. B.; Lamarche, V. M. E. J. Chem. Soc., Dalton Trans. 2002, 2413-2414.
23. (d) Avent, A. G.; Cloke, F. G. N.; Elvidge, B. R.; Hitchcock, P. B. Dalton Trans. 2004, 1083-1096.
24. Skvortsov, G. G.; Yakovenko, M. V.; Castro, P. M.; Fukin, G. K.; Cherkasov, A. V.; Carpentier, J.-F.; Trifonov, A. A. Eur. J. Inors. Chem. 2007, 3260-3267.
25. Ajellal, N.; Lyubov, D. M.; Sinenkov, M. A.; Fukin, G. K.; Cherkasov, A. V.; Thomas, C. M.; Carpentier, J.-F.; Trifonov, A. A. Chem.-Eur. J. 2008, 14, 5440-5448.
26. Manzer, L. E. Inors. Chem. 1978, 17, 1552-1558.
27. Mirsaidov, U.; Shaimuradov, I.; Hikmatov, M. Zh. Neors. Khim. (Russ. J. Inors. Chem.) 1986, 31, 1321-1326.
28. Svoboda, M.; Dieck, H. T. J. Orsanomet. Chem. 1980, 191, 321-327.
29. Barakat, I.; Dubois, P.; Jerome, R.; Teyssie, P. J.poolytrLjici. A poolxtrL Chem. 1993, 31, 505-514.
30. (a) Giesbrecht, G. R.; Whitener, G. D.; Arnold, J. J. Chem. Soc., Dalton Trans. 2001, 923-927.
31. (b) Ajellal, N.; Bouyahyi, M.; Amgoune, A.; Thomas, C. M.; Bondon, A.; Pillin, I.; Grohens, Y.; Carpentier, J.-F. Macromolecules 2009, 42, 987-993.
32. Sheldrick, G. M. SHELXTL, Structure Determination Software Suite, version 6.12; Bruker AXS: Madison, WI, 2000.
33. Sheldrick, G. M. SADABS, Bruker/Siemens Area Detector Absorption Correction Program; version 2.01; Bruker AXS: Madison, WI, 1998.
34. (a) Ephritikhine, M. Chem. Rev. 1997, 97, 2193-2242.
35. (b) Schumann, H.; Keitsch, M. R.; Demtschuk, J.; Muhle, S. Z. Anorg. Allg. Chem. 1998, 624, 1811-1818.
36. (a) Roesky, P. W. Organometallics 2002, 21, 4756-4761.
37. (b) Skinner, M. E. G.; Mountford, P. J. Chem. Soc., Dalton Trans. 2002, 1694-1703.
38. (c) Bambirra, S.; Boot, S. J.; van Leusen, D.; Meetsma, A.; Hessen, B. Organometallics 2004, 23, 1891-1898.
39. (d) Runte, O.; Priermeier, T.; Anwander, R. Chem. Commun. 1996, 1385-1386.
40. Cope-Eatough, E. K.; Mair, F. S.; Pritchard, R. G.; Warren, J. E.; Woods, R. J. Polyhedron 2003, 22, 1447-1454.
41. Allen, F. A.; Konnard, O.; Watson, D. G.; Brammer, L.; Orpen, G.; Taylor, R. J. Chem. Soc., Perkin Trans. 1987, 1-19.
42. (a) Trifonov, A. A.; Borovkov, I. A.; Fedorova, E. A.; Fukin, G. K.; Larionova, J.; Druzhkov, N. O.; Cherkasov, V. K. Chem.-Eur. J. 2007, 13, 4981-4987.
43. (b) De Waele, P.; Jazdzewski, B. A.; Klosin, J.; Murray, R. E.; Theriault, C. N.; Vosejpka, P. C.; Petersen, J. L. Organometallics 2007, 26, 3896-3899.
44. (c) Gorls, H.; Neumiiller, B.; Scholz, A.; Scholz, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 673-676.
45. (a) Evans, W. J.; Boyle, T. J.; Ziller, J. W. Orsanometallics 1993, 12, 3998-4009.
46. (b) Evans, W. J.; Sollberger, M. S.; Hanusa, T. P. J. Am. Chem. Soc. 1988, 110, 1841-1850.
47. (a) Guzei, I. A.; Wendt, M. Dalton Trans. 2006, 33, 3991-3999.
48. (b) Fukin, G. K.; Guzei, I. A.; Baranov, E. V. J. Coord. Chem. 2007, 60, 937-944.
49. (c) Fukin, G. K.; Guzei, I. A.; Baranov, E. V. J. Coord. Chem. 2008, 61, 1678-1688.
50. + fragments in 1 and 2 were performed using Gaussian 03 package on the basis of the X-ray geometry of complexes 1 and 2.
51. Segal, B. G.; Lippard, S. J. Inors. Chem. 1978, 17, 844-850.
52. Our recent investigations on bis(guanidinate) alkoxide complexes of lanthanides (Y, Nd, Lu) have shown that no evident differences in the performances (activity, control over the molecular weights, and molecular weight distributions) of tert-butoxide and iso-propoxide complexes [for a given metal] could be discerned in the ROP of lactide; see ref 7. Although only the tert-butoxide complex was prepared and investigated in ROP in the present study, an overall similar behavior can be anticipated for the iso-propoxide analogue {DAB}Y(OiPr)-(THF)(DME).
53. A blank experiment using LiBH4 showed that this compound is not active for the ROP of rac-lactide under the conditions used. This observation is in line with previous observations in the ROP of cyclic esters (e-caprolactone) and carbonates (TMC) [S. Guillaume, personal communication] and discards the possibility that ROP is initiated by LiBH4 arising from dissociation of complex 1.
54. From these data, the order in catalyst (2) and rate constant were roughly estimated as n = 0.74 ± 0.09 and k = 20.95 ± 5h-1 in THF, and n = 1.65 ± 0.2 and k = 3390 ± 650 h-1 in toluene, respectively.
55. MALDI-TOF-MS analysis of some PLA samples showed distributions containing both even-membered and odd-membered oligomers, with peaks separated by 72 Da; this unambiguously establishes that transesterification processes actually take place in these systems.
56. The nature of the terminus groups in PLAs produced with borohydride complex 3 could not be unambiguously identified. 1H and 13C NMR spectroscopy suggested that mixtures of PLAs having mostly CH2OH and possibly also CHO termini are the main products. For end-group analysis of polyesters produced from borohydride initiators, see: (a) Palard, I. A. S.; Guillaume, S. M. Chem.-Eur. J. 2004, 4054-4062.
57. (b) Guillaume, S. M.; Schappacher, M.; Soum, A. Macromolecules 2003, 36, 54-60.
58. (c) Palard, I.; Soum, A.; Guillaume, S. M. Macromolecules 2005, 38, 6888-6894.
59. (a) See ref 4i. Kricheldorf, H. R.; Berl, M.; Scharnagi, N. Macromolecules 1988, 21, 286-293.
60. (b) Dubois, P.; Jacobs, C.; Jerome, R.; Teyssie, P. Macromolecules 1991, 24, 2266-2270.