Synthesis, structure, and hydroamination kinetics of (2,2′- diaryldipyrrolylmethane)- and bis(2-arylpyrrolyl)titanium complexes

Organometallics

Volumn 25, Issue 26, 2006, Pages 6125-6133

  Swartz II, Douglas L ^a   Odom, Aaron L ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARENES; HYDROAMINATION; ISOSTERIC COMPLEXES; LIGANDS;

AMINATION; CARBOXYLIC ACIDS; COMPLEXATION; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); TITANIUM;

AROMATIC COMPOUNDS;

EID: 33846339684     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0607088     Document Type: Article

References (70)

1. (a) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
2. (b) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
3. (c) Duncan, A. P.; Bergman, R. G. Chem. Rec. 2002, 2, 431.
4. (d) Lee, S. Y.; Bergman, R. G. Tetrahedron 1995, 51, 4255.
5. (e) Poise, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 720, 13405.
6. Hill, J. E.; Profilet, R. D.; Fanwick, P. E.; Rothwell, I. P. Angew. Chem., Int. Ed. 1990, 29, 664.
7. (a) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
8. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
9. (c) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
10. (d) McOrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323.
11. Hazari, N.; Mountford, P. Acc. Chem. Res. 2005, 58, 839.
12. Odom, A. L. Dalton Trans. 2005, 225.
13. For some recent examples see: (a) Marcsekova, K.; Wegener, B.; Doye, S. Eur. J. Org. Chem. 2005, 4843.
14. (b) Smolensky, E.; Kapon, M.; Eisen, M. S. Organometallics 2005, 24, 5495.
15. (c) Heutling, A.; Pohlki, F.; Doye, S. Chem. Eur. J. 2004, 10, 3059.
16. (d) Ward, B. D.; Maisse-Francois, A.; Mountford, P.; Gade, L. H. Chem. Commun. 2004, 704.
17. (e) Lorber, C.; Choukroun, R.; Vendier, L. Organometallics 2004, 23, 1845.
18. (f) Ackermann, L. Organometallics 2003, 22, 4367.
19. (g) Zhang, Z.; Schafer, L. L. Org. Lett. 2003, 5, 4733.
20. (h) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 2541.
21. (i) Tillack, A.; Khedkar, V.; Beller, M. Tetrahedron Lett. 2004, 45, 8875.
22. (j) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923.
23. (k) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011.
24. (l) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3968.
25. (m) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389.
26. (a) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853.
27. (b) Ackermann, L.; Born, R. Tetrahedron Lett. 2004, 45, 9541.
28. (c) Khedkar, V.; Tillack, A.; Michalick, M.; Beller, M. Tetrahedron Lett. 2004, 45, 3123.
29. (d) Khedkar, V.; Tillack, A.; Michalik, M.; Beller, M. Tetrahedron 2005, 61, 7622.
30. Ramanathan, B.; Keith, A. J.; Armstrong, D.; Odom, A. L. Org. Lett. 2004, 6, 2957.
31. Cao, C.; Li, Y.; Shi, Y.; Odom, A. L. Chem. Commun. 2004, 2002.
32. Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880.
33. Banerjee, S.; Shi, Y.; Cao, C.; Odom, A. L. J. Organomet. Chem. 2005, 690, 5066.
34. (a) Kim, H.; Lee, P. H.; Livinghouse, T. Chem. Commun. 2005, 5205.
35. (b) Bexrud, J. A.; Beard, J. D.; Leitch, D. C.; Schafer, L. L. Org. Lett. 2005, 7, 1959.
36. (c) Hoover, J. M.; Petersen, J. R.; Pikul, J. H.; Johnson, A. R. Organometallics 2004, 23, 4614.
37. (d) Ackermann, L.; Bergman, R. G.; Loy, R. N. J. Am. Chem. Soc. 2003, 125, 11956.
38. (e) Li, C.; Thomson, R. K.; Gillon, B.; Patrick B. O.; Schafer, L. L. Chem. Commun. 2003, 2462.
39. (f) Bytschkov, I.; Doye. S. Tetrahedron Lett. 2002, 43, 3715.
40. (g) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475.
41. There is some evidence that cationic group 4 complexes use a 1,2-insertion mechanism similar to that found for lanthanide and group 3 based hydroamination catalysts. For examples of cationic zirconium hydroamination see: (a) Gribkov, D. V.; Hultzsch, K. C. Angew. Chem., Int. Ed. 2004, 43, 5542.
42. (b) Knight, P. D.; Munslow, I.; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894. For examples of hydroamination using the 1,2-insertion mechanism see:
43. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757.
44. (d) Seyam, A. M.; Stubbert, B. D.; Jensen, T. R.; O'Donnell, J. J., III; Stern, C. L.; Marks, T. J. Inorg. Chim. Acta 2004, 357, 4029.
45. (e) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705.
46. (f) Gagne, M. R.; Stern, C. L.; Marks, T. L. J. Am. Chem. Soc. 1992, 114, 275.
47. (g) Molander, G. A.; Romera, i. A. C. Chem. Rev. 2002, 102, 2161.
48. (h) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
49. (i) Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737.
50. (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632.
51. (b) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305.
52. Herrison, J.-L.; Chauvin, Y. Makromol. Chem. 1971, 141, 161.
53. Grubbs, R. H., Ed., Handbook of Metathesis; Wiley-VCH: Chichester, U.K., 2003.
54. Schreck, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
55. The added strength of dative interactions with the amines in solution could negate some of the effects of stronger alkyne/olefin binding. There could also be advantages to greater Lewis acidity in the [2 + 2] cycloaddition itself.
56. a of a ruthenium amine complex see: Fulton, J. R.; Sklenak, S.; Bouwkamp, M. W.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 4722.
57. Ciszewski, J. T.; Harrison, J. F.; Odom, A. L. Inorg. Chem. 2004, 43, 3605.
58. Shi, Y.; Hall, C.; Ciszewski, J. T.; Cao, C.; Odom, A. L. Chem. Commun. 2003, 586.
59. Littler, B. J.; Miller, M. A.; Hung, C.-H.; Wagner, R. W.; O'Shea, D. F.; Boyle, P. D.; Lindsey, J. S. J. Org. Chem. 1999, 64, 1391.
60. Rieth, R. D.; Mankad, N. P.; Calimano, E.; Sadighi, J. P. Org. Lett. 2004, 6, 3981.
61. Tanski, J. M.; Parkin, G. Organometallics 2002, 21, 587.
62. For a review on Cp and indenyl isomerization see: O'Conner, J. M.; Casey, C. P. Chem. Rev. 1987, 87, 307.
63. Hollis, T. K.; Ahn, Y. J.; Tham, F. S. Chem. Commun. 2002, 2996.
64. 1H NMR spectra which are presumably due to pyrrolyl crossover. Further study is warranted on these issues.
65. 2 (8). However, even with these, activation would occur at room temperature over a couple of hours if samples were allowed to rest before the kinetic run.
66. 2(dmpm) (1) would have been preferable. However, under these conditions at 100 °C the reaction was ∼50% complete in <10 min, making its measurements unreliable.
67. Banerjee, S.; Odom, A. L. Unpublished results.
68. Bradley, D. C.; Thomas, I. M. J. Chem. Soc. 1960, 3859.
69. Balboni, D.; Camuratti, G. P.; Resconi, L. Inorg. Chem. 2001, 40, 6588.
70. Espenson, J. H. Chemical Kinetics and Reaction Mechanisms; McGraw-Hill: New York, 1995.