Bis(imino)pyridine complexes of the first-row transition metals: Alternative methods of activation

Organometallics

Volumn 27, Issue 21, 2008, Pages 5712-5716

  Hanton, Martin J ^a   Tenza, Kenny ^a  

^a SASOL TECHNOLOGY PTY LTD   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINA; CHEMICAL ACTIVATION; CHROMIUM; CHROMIUM COMPOUNDS; COBALT; PYRIDINE; TRANSITION METALS; VANADIUM; VANADIUM COMPOUNDS;

ALTERNATIVE METHODS; CATALYST SYSTEMS; COST DRIVERS; PYRIDINE COMPLEXES;

IRON COMPOUNDS;

EID: 56049088745     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800744j     Document Type: Article

References (45)

1. (a) Small, B. L.; Brookhart, M.; Bennet, 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. Chem. Commun. 1998, 849.
3. (a) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 428.
4. (b) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283.
5. (c) Gibson, V. C.; Redshaw, C.; Solan, G. A. Chem. Rev. 2007, 107, 1745.
6. Knijnenburg, Q.; Gambarotta, S.; Budzelaar, P. H. M. Dalton Trans. 2006, 5442.
7. Tooze, R. P.; Hanton, M. J.; Tenza, K. (Sasol Technology) WO2008038173, 2008.
8. Tullo, A. H. Chem. Eng. News 2001, 79, 38.
9. (a) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
10. (b) Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345.
11. (a) Bochmann, M.; Sarsfield, M. J. Organometallics 1998, 17, 5908.
12. (b) McGuinness, D. S.; Overett, M.; Tooze, R. P.; Blann, K.; Dixon, J. T.; Slawin, A. M. Z. Organometallics 2007, 26, 1108.
13. (a) Pindado, G. J.; Thornten-Pett, M.; Bochmann, M. Dalton Trans. 1997, 3115.
14. (b) Pindado, G. J.; Bouwkamp, M.; Meetsma, A.; Hessen, B.; Thornten-Pett, M.; Bochmann, M. Angew. Chem., Int. Ed. 1997, 36, 2358.
15. (a) Krossing, I.; Raabe, I. Angew. Chem., Int. Ed. 2004, 43, 2066, and references therein.
16. (b) Krossing, I. Chem.-Eur. J. 2001, 7, 490.
17. (c) Ivanova, S. M.; Nolan, B. G.; Kobayashi, Y.; Miller, S. M.; Anderson, O. P.; Strauss, S. H. Chem.-Eur. J. 2001, 7, 503.
18. (a) McGuinness, D. S.; Rucklidge, A. J. (Sasol Technology UK) WO2007039851 A3, 2007.
19. (b) McGuinness, D. S.; Rucklidge, A. J.; Tooze, R. P.; Slawin, A. M. Z. Organometallics 2007, 26, 2561.
20. (c) Rucklidge, A. J.; McGuinness, D. S.; Tooze, R. P.; Slawin, A. M. Z.; Pelletier, J. D. A.; Hanton, M. J.; Webb, P. B. Organometallics 2007, 26, 2782.
21. (a) Scott, J.; Gambarotta, S.; Korobkov, I.; Budzelaar, P. H. M. Organometallics 2005, 24, 6398.
22. (b) Scott, J.; Gambarotta, S.; Korobkov, I.; Knijnenburg, Q.; de Bruin, D.; Budzelaar, P. H. M. J. Am. Chem. Soc. 2005, 127, 17204.
23. (c) Scott, J.; Gambarotta, S.; Korobkov, I.; Budzelaar, P. H. M. J. Am. Chem. Soc. 2005, 127, 13109.
24. Cámpora, J.; Naz, A. M.; Palma, P.; Alvarez, E. Organometallics 2005, 24, 4778.
25. (a) Bouwkamp, M. W.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2005, 127, 9660.
26. (b) Bouwkamp, M. W.; Bart, S. C.; Hawrelak, E. J.; Trovitch, R. J.; Lobkovsky, E.; Chirik, P. J. Chem. Commun. 2005, 3406.
27. (c) Bouwkamp, M. W.; Lobkovsky, E.; Chirik, P. J. Inorg. Chem. 2006, 45, 2.
28. (d) Bart, S. C.; Chlopek, K.; Bill, E.; Bouwkamp, M. W.; Lobkovsky, E.; Neese, F.; Wieghardt, K.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13901.
29. (e) Fernández, I.; Trovitch, R. J.; Lobkovsky, E.; Chirik, P. J. Organometallics 2008, 27, 109.
30. Kaul, F. A. R.; Puchta, G. T.; Schneider, H.; Grosche, M.; Mihalios, D.; Herrmann, W. A. J. Organomet. Chem. 2001, 621, 184.
31. (a) Small, B. L.; Marcucci, A. J. Organometallics 2001, 20, 5738.
32. (b) Small, B. L.; Baralt, E. J. US20020177744 A1, 2002.
33. Ionkin, A. S.; Johnson, L. K. (Du Pont) US0009597 A1, 2006.
34. It is well known that catalysts of this type are thermally sensitive, so control of the initial exotherm is crucial to obtain meaningful results. The autoclaves used for catalysis were Buchi Miniclave (250 mL) vessels, equipped with an integral flow jacket and internal cooling coil; thus significant cooling power could be achieved via the external thermal fluid circulated by a Haake bath and cold tap water feeding the cooling coil.
35. Further details of this comparison between entries 1 and 4 versus entries 2, 3, and 5 can be found in the Supporting Information, including gas uptake profiles.
36. In order to provide clarity during discussion, the terms TM activity and TM productivity are used to refer to those calculated on the transition metal, while the terms Al activity and Al productivity are used to refer to those figures based on the amount of trialkylaluminium used (and do not include the Al in the aluminate anion; hence 100 TEA + 1.5 TA, would use 100 equiv for the aluminium usage, not 101.5).
37. (a) Small, B. L.; Rios, R.; Fernandez, E. R.; Carney, M. J. Organometallics 2007, 26, 1744-1749.
38. (b) De Boer, E. J. M.; Deuling, H. H.; Van Der Heijden, H.; Meijboom, N.; Van Oort, A. B.; Van Zon, A. (Shell) US6710006, 2004.
39. iBu (25%).
40. (a) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049.
41. Krossing, I.; Brands, H.; Feuerhake, R.; Koenig, S. J. Fluorine Chem. 2001, 112, 83.
42. Small, B. L.; Schmidt, R. Chem.-Eur. J. 2004, 10, 1014.
43. Small, B. L.; Carney, M. J.; Holman, D. M.; O'Rourke, C. E.; Halfen, J. A. Macromolecules 2004, 37, 4375.
44. For general synthetic instructions regarding the preparation of bis(imino)pyridine Fe and Co complexes see: (a) Small, B. L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 7143.
45. (b) Britovsek, G. J. P.; Mastroianni, S.; Solan, G. A.; Baugh, S. P. D.; Redshaw, C.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; Elsegood, M. R. J. Chem.-Eur. J. 2000, 6, 2221.