Preparation of an active neodymium catalyst for regioselective butadiene cis-polymerization supported by a dianionic modification of the 2,6-diiminopyridine ligand

Organometallics

Volumn 23, Issue 21, 2004, Pages 5054-5061

  Sugiyama, Hiroyasu ^a   Gambarotta, Sandro ^a   Yap, Glenn P A ^a   Wilson, David R ^b   Thiele, Sven K H ^c  

^a UNIVERSITY OF OTTAWA   (Canada)

^b DOW CHEMICAL COMPANY   (United States)

^c Dow Olefinverbund GmbH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DEPROTONATION; ELECTRONIC CHARGE; LIGANDS; NEODYMIUM CATALYSTS;

ALKYLATION; CATALYST ACTIVITY; CATALYSTS; CHARGE COUPLED DEVICES; CRYSTALLOGRAPHY; POLYMERIZATION; SUBSTRATES; X RAYS;

NEODYMIUM;

EID: 6344223575     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0496434     Document Type: Article

References (53)

1. (a) Small, B. L.; Brookhart, M. S.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049.
2. (b) Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1998, 849.
3. (c) Esteruelas, M. A.; Lopez, A. M.; Mendez, L.; Olivan, M.; Onate, E. Organometallics 2003, 22, 395.
4. (d) Bryliakov, K. P.; Semikolenova, N. V.; Zudin, V. N.; Zakharov, V. A.; Talsi, E. P. Catal. Commun. 2004, 5, 45.
5. (e) Britovsek, G. J. P.; Gibson, V. C.; Spitzmesser, S. K.; Tellmann, K. P.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Dalton Trans. 2002, 6, 1159.
6. (a) Budzelaar, P. H. M.; de Bruin, B.; Gal, A. W.; Wieghardt, K.; van Lenthe, J. H. Inorg. Chem. 2001, 40, 4649.
7. (b) Margl, P.; Deng, L.; Ziegler, T. Organometallics 1999, 18, 5701.
8. (c) Griffiths, E. A. H.; Britovsek, G. J. P.; Gibson, V. C.; Gould, I. R. Chem. Commun. 1999, 1333.
9. (a) Bruce, M.; Gibson, V. C.; Redshaw, C.; Solan, G. A.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1998, 2523.
10. (b) Korotakov, I.; Gamtaarotta, S.; Yap, G. P. A.; Budzelaar, P. H. M. Organometallics 2002, 21, 3088.
11. (c) Clentsmith, G. K. B.; Gibson, V. C.; Hitchcock, P. B.; Kimberly, B. S.; Rees, C. W. J. Chem. Soc., Chem. Commun. 2002, 1498.
12. (d) Kooistra, T. M.; Knijnenburg, Q.; Smits; J. M. M.; Horton, A. D.; Budzelaar, P. H. M.; Gal, A. W. Angew. Chem., Int. Ed. 2001, 40, 4719.
13. (e) Gibson, V. C.; Humphries, M. J.; Tellmann, K. P.; Wass, D. F.; White, A. J. P.; Williams, D. J. Chem. Commun. 2001, 2252.
14. (f) Gibson, V. C.; Tellmann, K. P.; Humphries, M. J.; Wass, D. F. Chem. Commun. 2002, 2316.
15. (g) Britovsek, G. J. P.; Bruce, M.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; Mastroianni, S.; McTavish, S. J.; Redshaw, C.; Solan, G. A.; Stroemberg, S.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 8728.
16. (a) Reardon, D.; Conan, F.; Gambarotta, S.; Yap, G. P. A.; Wang, Q. J. Am. Chem. Soc. 1999, 121, 9318.
17. (b) Sugiyama, H.; Aharonian, G.; Gambarotta, S.; Yap, G. P. A.; Budzelaar, P. H. M. J. Am. Chem. Soc 2002, 124, 12268.
18. (c) Reardon, D.; Aharonian, G.; Gambarotta, S.; Yap, G. P. A. Organometallics 2002, 21, 786.
19. (d) De Bruin, B.; Bothe, E.; Weyhermuller, T.; Wieghardt, K. Inorg. Chem. 2000, 39, 2936.
20. Enright, D.; Gambarotta, S.; Yap, G. P. A.; Budzelaar, P. H. M. Angew. Chem., Int. Ed. 2002, 41, 3873.
21. Sugiyama, H.; Korobkov, I.; Gambarotta, S.; Möller, A.; Budzelaar, P. H. M. Inorg. Chem., in press.
22. (a) Estler, F.; Eickerling, G.; Herdtweck, E.; Anwander, R. Organometallica 2003, 22, 1212.
23. (b) Ward, B. D.; Dubberley, S. R.; Maisse-François, A.; Gade, L. H.; Mountford, P. J. Chem. Soc., Dalton Trans. 2002, 4649.
24. (c) Piers, W. E.; Emslie, D. J. H. Coord. Chem. Rev. 2002, 233-234, 131.
25. (a) Hou, Z.; Wakatsuki, Y. Coord. Chem. Rev. 2002, 231, 1.
26. (b) Yasuda, H. Top. Organomet. Chem. 1999, 2, 255.
27. 3 was prepared following a standard procedure: (a) Freeman, J. H.; Smith, M. L. J. Inorg. Nucl. Chem. 1988, 7, 224, and was transformed into the corresponding tetrahydrofuranate. (b) Manzer, L. E. Inorg. Synth. 1982, 21, 135. (c) Angelica, R. J. Inorg. Synth. 1990, 27, 136.
28. 3 was prepared following a standard procedure: (a) Freeman, J. H.; Smith, M. L. J. Inorg. Nucl. Chem. 1988, 7, 224, and was transformed into the corresponding tetrahydrofuranate. (b) Manzer, L. E. Inorg. Synth. 1982, 21, 135. (c) Angelica, R. J. Inorg. Synth. 1990, 27, 136.
29. 3 was prepared following a standard procedure: (a) Freeman, J. H.; Smith, M. L. J. Inorg. Nucl. Chem. 1988, 7, 224, and was transformed into the corresponding tetrahydrofuranate. (b) Manzer, L. E. Inorg. Synth. 1982, 21, 135. (c) Angelica, R. J. Inorg. Synth. 1990, 27, 136.
30. (a) Mabbs, M. B.; Machin, D. Magnetism and Transition Metal Complexes; Chapman and Hall: London, 1973.
31. (b) Foese, G.; Gorter, C. J.; Smits, L. J. Constantes Selectionnes, Diamagnetisme, Paramagnetism, Relaxation Paramagnetique; Masson: Paris, 1957.
32. Blessing, R. Acta Crystallogr. 1995, A51, 33.
33. Nuckel, S.; Burger, P. Organometallies 2000, 19, 3305.
34. See for example: (a) Graf, D. D.; Davis, W. M.; Schrock, E. E.; Organometallice 1998, 17, 5820.
35. (b) Pryzuk, M. D.; Yu, P.; Patrick, B. O.; Can. J. Chem. 2001, 79, 1194.
36. (o) Lee, L.; Berg, D. J.; Bushnell, G. W.; Inorg, Chem. 1994, 33, 5302.
37. See for example: (a) Taube, E.; Maiwald, S.; Sieler, S. J. Organomet. Chem. 2001, 621, 327. (b) Wu, W.; Chen, M.; Zhou, P. Organometallics 1991, 10, 98
38. See for example: (a) Taube, E.; Maiwald, S.; Sieler, S. J. Organomet. Chem. 2001, 621, 327. (b) Wu, W.; Chen, M.; Zhou, P. Organometallics 1991, 10, 98
39. There are a few example of this type of bonding for allylic groups; see for example: (a) Perez, J.; Riera, V.; Rodriguez, A.; Garcia-Granda, S. Angew. Chem., Int. Ed. 2002, 41, 1427. (b) Barbaro, P.; Currao, A.; Hermann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics 1996, 15, 1879. (c) Abbenhuis, H. C. L.; Burokhardt, U.; Gramlich, V.; Martelletti, A.; Spencer, J.; Steiner, I.; Togni, A. Organometallics 1996, 15, 1614.
40. There are a few example of this type of bonding for allylic groups; see for example: (a) Perez, J.; Riera, V.; Rodriguez, A.; Garcia-Granda, S. Angew. Chem., Int. Ed. 2002, 41, 1427. (b) Barbaro, P.; Currao, A.; Hermann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics 1996, 15, 1879. (c) Abbenhuis, H. C. L.; Burokhardt, U.; Gramlich, V.; Martelletti, A.; Spencer, J.; Steiner, I.; Togni, A. Organometallics 1996, 15, 1614.
41. There are a few example of this type of bonding for allylic groups; see for example: (a) Perez, J.; Riera, V.; Rodriguez, A.; Garcia-Granda, S. Angew. Chem., Int. Ed. 2002, 41, 1427. (b) Barbaro, P.; Currao, A.; Hermann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics 1996, 15, 1879. (c) Abbenhuis, H. C. L.; Burokhardt, U.; Gramlich, V.; Martelletti, A.; Spencer, J.; Steiner, I.; Togni, A. Organometallics 1996, 15, 1614.
42. (a) Taube, R.; Windisch, H.; Maiwald, S.; Hemling, H.; Schumann, H. J. Organomet. Chem. 1996, 513, 49.
43. (b) Taube, R.; Windiach, H.; Hemling, H.; Schumann, H. J. Organomet. Chem. 1998, 555, 201.
44. (c) Taube, R.; Windisch, H.; Görlitz, P. H.; Schumann, H. J. Organomet. Chem. 1993, 445, 85.
45. (d) Maiwald, S.; Taube, R.; Hemling, H.; Schumann, H. J. Organomet. Chem. 1998, 552, 195.
46. (a) Gehrke, K.; Harwart, M. Plast. Kautsch. 1993, 40, 356.
47. (b) Anzai, S.; Irako, K.; Onishi, A.; Furukawa, J. Kogyo Kagaku Zasshi 1969, 72, 2081.
48. (c) Kaita, S.; Kobayashi, E.; Sakikibara, S.; Aoshima, S.; Furukawa, J. J. Polym Sci. Polym. Chem. Ed. 1996, 34, 3431.
49. (d) Oehme, A.; Gebauer, U.; Gehrke, K. Macromol. Rapid Commun. 1995, 16, 563.
50. (e) Zambelli, A.; Proto, A.; Longo, P.; Oliva, P. Macromol. Chem. Phys. 1994, 195, 2623.
51. (a) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078.
52. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539.
53. Yang, J. H.; Tsutsui, M.; Chen, Z.; Bergbreiter, D. E. Macromolecules 1982, 15, 230.