Group-4 transition-metal boryl complexes: Syntheses, structures, boron-metal bonding properties, and application as a polymerization catalyst

Journal of the American Chemical Society

Volumn 131, Issue 40, 2009, Pages 14162-14163

  Terabayashi, Tomomi ^a   Kajiwara, Takashi ^a   Yamashita, Makoto ^a   Nozaki, Kyoko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORYLATION; CHEMICAL EQUATIONS; COVALENT CHARACTER; METAL BONDING; METAL BONDS; POLYMERIZATION CATALYSTS; THEORETICAL CALCULATIONS;

BORON; BORON COMPOUNDS; ETHYLENE; POLYMERIZATION; SYNTHESIS (CHEMICAL); TRANSITION METALS;

STRUCTURAL METALS;

BORON DERIVATIVE; BORYLHAFNIUM; BORYLLITHIUM; BORYLTITANIUM TRIISOPROPOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 70349905240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905950g     Document Type: Article

References (66)

1. (a) Irvine, G. J.; Lesley, M. J. G.; Marder, T. B.; Norman, N. C.; Rice, C. R.; Robins, E. G.; Roper, W. R.; Whittell, G. R.; Wright, L. J. Chem. Rev. 1998, 98, 2685.
2. (b) Smith, M. R., III. Prog. Inorg. Chem. 1999, 48, 505.
3. (c) Braunschweig, H.; Colling, M. Coord. Chem. Rev. 2001, 223, 1.
4. (d) Aldridge, S.; Coombs, D. L. Coord. Chem. Rev. 2004, 248, 535.
5. (e) Braunschweig, H.; Kollann, C.; Rais, D. Angew. Chem., Int. Ed. 2006, 45, 5254.
6. (f) Kays, D. L.; Aldridge, S. In Contemporary Metal Boron Chemistry I: Borylenes, Boryls, Borane; Springer-Verlag: Berlin, 2008; Vol.130, pp 29-122.
7. (a) Zhu, J.; Lin, Z. Y.; Marder, T. B. Inorg. Chem. 2005, 44, 9384.
8. (b) Braunschweig, H.; Brenner, P.; Müller, A.; Radacki, K.; Rais, D.; Uttinger, K. Chem. - Eur. J. 2007, 13, 7171.
9. (c) Braunschweig, H.; Radacki, K.; Uttinger, K. Chem. - Eur. J. 2008, 14, 7858.
10. (d) Braunschweig, H.; Green, H.; Radacki, K.; Uttinger, K. Dalton Trans. 2008, 3531.
11. (e) Dang, L.; Zhao, H.; Lin, Z.; Marder, T. B. Organometallics 2008, 27, 1178.
12. (f) Braunschweig, H.; Leech, R.; Rais, D.; Radacki, K.; Uttinger, K. Organometallics 2008, 27, 418.
13. (g) Braunschweig, H.; Fuss, M.; Radacki, K.; Uttinger, K. Z. Anorg. Allg. Chem. 2009, 635, 208.
14. Segawa, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2007, 46, 6710.
15. (a) Nguyen, P.; Blom, H. P.; Westcott, S. A.; Taylor, N. J.; Marder, T. B. J. Am. Chem. Soc. 1993, 115, 9329.
16. (b) Cho, J.-Y.; Iverson, C. N.; Smith, M. R. J. Am. Chem. Soc. 2000, 122, 12868.
17. (c) Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 1999, 121, 7696.
18. (d) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305.
19. (e) Waltz, K. M.; He, X. M.; Muhoro, C.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11357.
20. (f) Waltz, K. M.; Hartwig, J. F. Science 1997, 277, 211.
21. (g) Chen, H. Y.; Hartwig, J. F. Angew. Chem., Int. Ed. 1999, 38, 3391.
22. (h) Waltz, K. M.; Muhoro, C. N.; Hartwig, J. F. Organometallics 1999, 18, 3383.
23. (i) Chen, H. Y.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
24. (j) Waltz, K. M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 11358.
25. (k) Kawamura, K.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8422.
26. (l) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
27. (m) Ishiyama, T. J. Synth. Org. Chem. Jpn. 2003, 61, 1176.
28. (n) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3.
29. (o) Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271.
30. (p) Ishiyama, T.; Miyaura, N. Pure Appl. Chem. 2006, 78, 1369.
31. (a) Hartwig, J. F.; De Gala, S. R. J. Am. Chem. Soc. 1994, 116, 3661.
32. (b) Lantero, D. R.; Motry, D. H.; Ward, D. L.; Smith, M. R., III. J. Am. Chem. Soc. 1994, 116, 10811.
33. (c) Lantero, D. R.; Ward, D. L.; Smith, M. R., III. J. Am. Chem. Soc. 1997, 119, 9699-9708.
34. (d) Lantero, D. R.; Miller, S. L.; Cho, J.-Y.; Ward, D. L.; Smith, M. R., III. Organometallics 1999, 18, 235.
35. (a) Hartwig, J. F.; Muhoro, G. N.; He, X. M.; Eisenstein, O.; Bosque, R.; Maseras, F. J. Am. Chem. Soc. 1996, 118, 10936.
36. (b) Muhoro, C. N.; Hartwig, J. F. Angew. Chem., Int. Ed. 1997, 36, 1510.
37. (c) Muhoro, C. N.; He, X. M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 5033.
38. (d) Hartwig, J. F.; Muhoro, C. N. Organometallics 2000, 19, 30.
39. A gallylzirconium complex possessing a heavier group-13 element, gallium, has also been synthesized via oxidative addition of digallane to low-valent zirconium. See: Baker, R. J.; Jones, C.; Murphy, D. M. Chem. Commun. 2005, 1339.
40. Group-3 gallyl complexes have been synthesized using a gallyl anion. See: (a) Arnold, P. L.; Liddle, S. T.; McMaster, J.; Jones, C.; Mills, D. P. J. Am. Chem. Soc. 2007, 129, 5360.
41. (b) Jones, C.; Stasch, A.; Woodul, W. D. Chem. Commun. 2009, 113.
42. (c) Liddle, S. T.; McMaster, J.; Mills, D. P.; Blake, A. J.; Jones, C.; Woodul, W. D. Angew. Chem., Int. Ed. 2009, 48, 1077.
43. (d) Liddle, S. T.; Mills, D. P.; Gardner, B. M.; McMaster, J.; Jones, C.; Woodul, W. D. Inorg. Chem. 2009, 48, 3520.
44. Segawa, Y.; Yamashita, M.; Nozaki, K. Science 2006, 314, 113.
45. Segawa, Y.; Suzuki, Y.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2008, 130, 16069.
46. Yamashita, M.; Suzuki, Y.; Segawa, Y.; Nozaki, K. Chem. Lett. 2008, 37, 802.
47. (a) Marder, T. B. Science 2006, 314, 69.
48. (b) Braunschweig, H. Angew. Chem., Int. Ed. 2007, 46, 1946.
49. 2K with them occured at the metal center, not on the boron atom.
50. The stability of 2 and 3 shows that the boryl ligand can coexist in the coordination sphere with other nucleophilic ligands such as alkoxides and alkyls.
51. There has been one report of a borylosmium complex having intramolecular coordination of an alcoholic OH group to the metal center. See: Rickard, C. E. F.; Roper, W. R.; Williamson, A.; Wright, L. J. J. Organomet. Chem. 2004, 689, 1609.
52. (a) Alcaraz, G.; Sabo-Etienne, S. Coord. Chem. Rev. 2008, 252, 2395.
53. (b) Lin, Z. In Contemporary Metal Boron Chemistry I: Borylenes, Boryls, Borane; Springer-Verlag: Berlin, 2008; Vol.130, pp 123-148.
54. The Cambridge Crystallographic Database listed all of the structurally characterized Ti and Hf complexes having relatively short interatomic metalboron distances. For all of these references, see the Supporting Information.
55. Emsley, J. The Elements; Oxford University Press: New York, 1998.
56. 3. See: Chesnut, R. W.; Durfee, L. D.; Fanwick, P. E.; Rothwell, I. P.; Folting, K.; Huffman, J. C. Polyhedron 1987, 6, 2019.
57. (a) Yasumoto, T.; Yamagata, T.; Mashima, K. Organometallics 2005, 24, 3375.
58. (b) Swenson, D. C.; Guo, Z.; Crowther, D. J.; Baenzigera, N. C.; Jordan, R. F. Acta Crystallogr. 2000, C56, E313.
59. (c) Kissounko, D. A.; Zhang, Y.; Harney, M. B.; Sita, L. R. Adv. Synth. Catal. 2005, 347, 426.
60. It was confirmed that this difference in the orientation angles of the diazaborole rings in 3 and 6 did not affect the bonding character. See the Supporting Information.
61. 1.237 hybridized orbital.
62. 2ρ(r) values, indicating ionic character of the B-Li bond. See ref 10 and the Supporting Information.
63. For PE, see: (a) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H.-G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
64. (b) Hessen, B.; van der Heijden, H. J. Organomet. Chem. 1997, 534, 237.
65. (c) Lee, K.-S.; Kim, Y.; Ihm, S.-K.; Do, Y.; Lee, S. J. Organomet. Chem. 2006, 691, 1121.
66. (d) Zhang, W.; Wei, J.; Sita, L. R. Macromolecules 2008, 41, 7829. For PHex, see refs 20a, c and 24d.