Synthesis of group 4 metal amides with new chiral biaryldiamine-based ligands and their use as catalysts for asymmetric hydroamination/cyclization

Organometallics

Volumn 28, Issue 4, 2009, Pages 1127-1137

  Guofu, Zi ^a   Xue, Liu ^a   Li, Xiang ^a   Haibin, Song ^b  

^a BEIJING NORMAL UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYSTS; BINAPHTHYL; CHIRAL LIGANDS; CYCLIC AMINES; ELEMENTAL ANALYSIS; GOOD YIELDS; GROUP 4; METAL AMIDES; N HEXANES; NEW SERIES; REACTION CONDITIONS; RECRYSTALLIZATION; SOLID-STATE STRUCTURES; SPECTROSCOPIC TECHNIQUES; TOLUENE SOLUTIONS;

AMIDES; AMINATION; AMINES; CATALYSIS; CATALYSTS; CHELATION; FULLERENES; HEXANE; LIGANDS; RECRYSTALLIZATION (METALLURGY); TITANIUM; TOLUENE; X RAY DIFFRACTION ANALYSIS;

ZIRCONIUM;

EID: 64549142832     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om801061v     Document Type: Article

References (70)

1. for reviews of asymmetrrc hvdroamination. see: (a) Roesky, P. W.; Müller. T. E. Angew. Chem., Int. Ed. 2003, 42, 2708-2710.
2. (b) Hong. S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
3. (c) Hultzsch, K. C. Org. Bwmol. Chem. 2005, 3, 1819-1824.
4. (d) Hultzsch, K. C.Adv. Synth. Catal. 2005, 347, 367-391.
5. (e) Hii, K. K. Pure Appl. Chem. 2006, 78, 341-349.
6. (f) Aillaud, I.; Collin, J.; Hannedouche, J.; Schulz, E. Dalton Trans. 2007, 5105-5118.
7. (g) Müller, T. E.; Hultzsch, K. C; Yus. M.; Foubelo. R; Tada. M. Chem. Rev. 2008, 108, 3795-3892.
8. For selected papers for asymmetric hydroaminations using lanthanide metal catalysts with chiral Cp ligands, see: (a) Gagne, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294.
9. (b) Gagné, M. R.; Brard, L.; Conticello, V. P.; Giardello, M. A.; Stern, C. L.; Marks, T. J. Organometallics 1992, 11, 2003-2005.
10. (c) Vitanova, D. V.; Hampel, F.; Hultzsch, K. C. J. Oreanomet. Chem. 2007, 692, 4690-4701, and references therein.
11. Hong, S.; Tian, S.; Metz, M. V.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 14768-14783.
12. (a) O'Shaughnessy, P. N.; Knight, P. D.; Morton, C; Gillespie, K. M.; Scott, P. Chem. Commun. 2003, 1770-1771.
13. (b) O'Shaughnessy, P. N.; Gillespie, K. M.; Knight, P. D.: Munslow, I. J.: Scott, P. Dalton Trans 2004, 2251-2256.
14. Kim. J. Y.: Livinghouse. T. Org. Lett. 2005, 7, 1737-1739.
15. (a) Gribkov. D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748-3759.
16. (b) Gribkov, D. V.; Hultzsch, K. C. Chem. Commun. 2004, 730-731.
17. (c) Gribkov, D. V.; Hampel, F.; Hultzsch, K. C. Eur. J. Inorg. Chem. 2004, 409, 1-4101.
18. (d) Gribkov. D. V.; Hultzsch, K. C; Hampel. F. Chem.-Eur. J. 2003, 9, 4796-4810.
19. (e) Yu. X.; Marks. T. J. Organometallics 2007, 26, 365-376.
20. (f) Heck, R.: Schulz, E.: Collin, J.; Carpentier, J.-F. J. Catal. A: Chem. 2007, 268, 163-168.
21. (a) Riegert, D.; Collin, J.; Meddour. A.; Schulz, E.; Trifonov, A. J. Org. Chem. 2006, 71, 2514-2517.
22. (b) Collin, J.; Daran. J. C; Jacquet. O.; Schulz, E.; Trifonov, A. Chem.-Eur. J. 2005, 11, 3455-3462.
23. (c) Collin, J.; Daran, J. C; Schulz, E.; Trifonov, A. Chem. Commun. 2003, 3048-3049.
24. (d) O'Shaughnessy, P. N.; Scott, P. Tetrahedron: Asymmetry 2003, 14, 1979-1983.
25. (e) Meyer. N.; Zulys. A.: Roesky, P. W. Organometallics 2006, 25, 4179-4182.
26. (f) Riegert, D.; Collin, J.; Daran, J. C; Fillebeen, T.; Schulz, E.; Lyubov, D.; Fukin, G.; Trifonov, A. Eur. J. Inorg. Chem. 2007, 115, 9-1168.
27. (g) Kim. H.; Kim, Y. K.; Shim, J. Ft.; Kim. M.; Han. M.; Livinghouse, T.; Eee, P. H. Adv. Synth. Catal. 2006, 348, 2609-2618.
28. (h) Aillaud, I.; Wright, K.; Collin. J.; Schulz, E.; Mazalevrat. J.-P. Tetrahedron: Asmmetry 2008, 19, 82-92.
29. (i) Aillaud, I.; Collin, J.'; Duhayon, C; Guillot, R.; Lyubov, D.; Schulz, E.; Trifonov, A. Chem-Eur. J. 2008, 14, 2189-2200.
30. (j) Hannedouche, J.; Aillaud, I.; Collin, J.; Schulz, E.; Trifonov, A. Chem. Commun. 2008, 3552-3554.
31. (k) Aillaud, I; Lyubov, D.; Collin, J.; uillot, R.; Hannedouche, J.; Schulz. E.; Trifonov, A. Oganometallics 2008, 27, 5929-5936.
32. For asymmetric hydroamination using late transition metal catalysts, see: (a) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366-4367.
33. (b) Patil, N. T.; Lutete, L. M.: Wu, H.: Pahadi, N. K.; Gridnev. I. D.: Yamamoto, Y. J. Org. Chem. 2006, 71, 4270-4279.
34. (c) Hu, A.; Ogasaware, M.; Sakamoto, T.; Okada, A.; Nakajima, K.; Takahashi, T.; Lin. W. Adv. Synth. Catal. 2006, 348, 2051-2056.
35. (d) LaLonde. R. L.; Sherry, B. D.; Kang, E. J.: Toste, F. D. J. Am. Chem. Soc. 2007,129, 2452-2453.
36. (e) Zhang. Z.; Bender, C. R: Widenhoefer, R. A. Org. Lett. 2007, 9,2887-2889.
37. (f) Zhang, Z.; Bender. C. F.; Widenhoefer. R. A. J. Am. Chem. Soc. 2007, 129, 14148-14149.
38. For examples of asymmetric hydroamination using other metal catalysts, see: (a) Knight, P. D.; Munslow, L; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894-895.
39. (b) Gribkov. D. V.; Hultzcsh. K. C. Angew. Chem., Int. Ed. 2004, 43, 5542-5546.
40. (c) Martinez, P. H.; Hultzsch, K. C; Hampel, F. Chem. Commun. 2006, 2221-2223.
41. (d) Watson, D. A.: Chiu, M.; Bergman, R. G. Organometallics 2006, 25, 4731-4733.
42. (e) Wood, M. C: Leitch, D. C: Yeung, C. S.; Kozak, J. A.; Schafer, L. L. Angew. Chem., Int. Ed. 2007, 46, 354-358.
43. (f) Gott, A. L.; Clarke, A. J.; Clarkson, G. J.; Scott, P. Organometallics 2007, 26, 1729-1737.
44. (g) Ogata, T.; Ujihara, A.; Tsuchida, S.; Shimizu. T.; Kaneshige, A.; Tomioka, K. Tetrahedron Lett. 2007, 48, 6648-6650.
45. (a) Xiang, L.; Wang, Q.: Song. H.; Zi, G. Organometallics 2007, 26, 5323-5329.
46. (b) Zi, G.: Xiang, L.; Song, H. Organometallics 2008, 27, 1242-1246.
47. (c) Xiang, L.; Song, H.: Zi, G. Eur. J. Inorg. Chem. 2008, 113, 5-1140.
48. (d) Zi, G.; Wang. Q.; Xiang, L.: Song. H. Dalton Trans. 2008, 5930-5944.
49. (e) Wang. Q.; Xiang, L.; Zi, G.; Song, H. Inorg. Chem. 2008, 47, 4319-4328.
50. (f) Wang, Q.; Xiang, L.; Song, H.; Zi, G. J. Organomet. Chem. published online 2008, http://dx.doi.org/10.1016/j.jorganchem.2008.11.061.
51. (a) Zi, G.; Xiang, L.: Zhang, Y.; Wang. Q.; Zhang, Z. Appl. Organomet. Chem. 2007, 21, 177-183.
52. (b) Brown, K. J.; Berry, M. S.; Murdoch, J. R. J. Org. Chem. 1985, 50, 4345-4349.
53. Korostylev, A.; Tararov, V. I.; Fischer, C; Monsees, A.; Borner, A. J. Org. Chem. 2004, 69, 3220-3221.
54. Kanoh, S.: Goka, S.; Murose, N.; Kubo. H.; Kondo, M.; Sugino. T.; Motoi, M.; Suda, H. Polym. J. 1987, 19, 1047-1065.
55. Diamond, G. M.; Jordan, R. F.; Petersen. J. L. J. Am. Chem. Soc. 1996, 118, 8024-8033.
56. (a) Wang, C.-J.; Shi, M. J. Org. Chem. 2003, 68, 6229-6237.
57. (b) Wang, J.; Li, H.; Duan. W.; Zu, L.; Wang. W. Org. Lett. 2005, 7, 4713-4716.
58. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Gottingen: Gottingen, Germany, 1996.
59. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure from Diffraction Data; University of Göttingen: Göttingen, Germany. 1997.
60. Jones. M. D.; Almeida Paz, F. A.; Davies, J. E.; Johnson. B. F. G. Acta Crystallogr. 2003, E59, o910-o912.
61. Song, H.; Gu, L.-N.; Zi, G. J. Organomet. Chem., published online 2009, http://dx.doi.org/10.1016/j.jorganchem.2008.12.059.
62. For selected recent papers, see: (a) Diamond. G. M.; Jordan. R. F.; Petersen, J. L. Organometallics 1996, 15, 4045-4053.
63. (b) Hughes, A. K.; Meetsma. A;.; Teuben. J. H. Organometallics 1993, 12, 1936-1945.
64. (c) Carpenetti, D. W.; Kloppenburg. L.; Kupec, J. T.; Petersen, J. L. Organometallics 1996, 15, 1572-1581.
65. (d) Zi, G.; Li, H.-W.; Xie, Z. Organometallics 2002, 21, 3850-3855.
66. (e) Tonzetich. Z. J.; Schrock, R. R.; Hock, A. S.; Miiller, P. Organometallics 2005, 24, 3335-3342.
67. (f) Crust. E. J.; Clarke, A. J.; Deeth, R. J.; Morton, C; Scott, P. Dalton Trans. 2004, 4050-4058.
68. (g) Majumder, S.; Odom, A. L. Organometallics 2008, 27, 1174-1177.
69. (a) Beesley, R. M.; Ingold. C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080-1106.
70. (b) Ingold, C. K. J. Chem. Soc. 1921, 119, 305-329.