Synthesis, structural characterization, and reactivity of organolanthanides derived from a new chiral ligand, (R)-bis(pyrrol-2-ylmethyleneamino)-1, 1′-binaphthyl

Organometallics

Volumn 26, Issue 22, 2007, Pages 5323-5329

  Xiang, Li ^a   Wang, Qiuwen ^a   Song, Haibin ^b   Zi, Guofu ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CHARACTERIZATION; CHIRALITY; CONDENSATION; CYCLIZATION; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); TOLUENE; X RAY DIFFRACTION ANALYSIS;

METATHESIS REACTIONS; ORGANOLANTHANIDE AMIDES; REFLUX;

LIGANDS;

EID: 35748955205     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7006826     Document Type: Article

References (61)

1. For general hydroamination reviews, see: (a) Odom, A. L. Dalton Trans. 2005, 225.
2. (b) Doye, S. Synlett 2004, 1653.
3. (c) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
4. (d) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935.
5. (e) Seayad, J.; Tillack, A.; Hartung, C. G.; Beller, M. Adv. Synth. Catai. 2002, 344, 795.
6. (f) Nobis, M.; Driessen-Hölscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983.
7. (g) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
8. For reviews of asymmetric hydroamination, see: (a) Roesky, P. W.; Müller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708.
9. (b) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
10. (c) Hultzsch, K. C. Org. Biomol. Chem. 2005, 3, 1819.
11. (d) Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367.
12. (e) Hii, K. K. Pure Appl. Chem. 2006, 78, 341.
13. For selected recent papers, see: (a) Giardello, M. A.; Conticello, V. P.; Brard, L.; Sabat, M.; Rheingold, A. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10212.
14. (b) Gagné, M. R.; Brard, L.; Conticello, V. P.; Giardello, M. A.; Stern, C. L.; Marks, T. J. Organometallics 1992, 11, 2003.
15. (c) Vitanova, D. V.; Hampel, F.; Hultzsch, K. C. J. Organometal. Chem., published online 2007, http://dx.doi.Org/10.1016/j.jorganchem.2007. 05.010, and references therein.
16. Hong, S.; Tian, S.; Metz, M. V.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 14768.
17. (a) O'Shaughnessy, P. N.; Knight, P. D.; Morton, C.; Gillespie, K. M.; Scott, P. Chem. Commun. 2003, 1770.
18. (b) O'Shaughnessy, P. N.; Gillespie, K. M.; Knight, P. D.; Munslow, I. J.; Scott, P. Dalton Trans. 2004, 2251.
19. Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737.
20. (a) Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748.
21. (b) Gribkov, D. V.; Hultzsch, K. C. Chem. Commun. 2004, 730.
22. (c) Gribkov, D. V.; Hampel, F.; Hultzsch, K. C. Eur. J. Inorg. Chem. 2004, 4091.
23. (d) Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. Chem. Eur. J. 2003, 9, 4796.
24. (e) Yu, X.; Marks, T. J. Organometallics 2007, 26, 365.
25. (a) Riegert, D.; Collin, J.; Meddour, A.; Schulz, E.; Trifonov, A. J. Org. Chem. 2006, 71, 2514.
26. (b) Collin, J.; Daran, J. C.; Jacquet, O.; Schulz, E.; Trifonov, A. Chem. Eur. J. 2005, 11, 3455.
27. (c) Collin, J.; Daran, J. C.; Schulz, E.; Trifonov, A. Chem. Commun. 2003, 3048.
28. (d) O'Shaughnessy, P. N.; Scott, P. Tetrahedron: Asymmetry 2003, 14, 1979.
29. (e) Meyer, N.; Zulys, A.; Roesky, P. W. Organometallics 2006, 25, 4179.
30. (f) Riegert, D.; Collin, J.; Daran, J. C.; Fillebeen, T.; Schulz, E.; Lyubov, D.; Fukin, G.; Trifonov, A. Eur. J. Inorg. Chem. 2007, 1159.
31. (g) Kim, H.; Kim, Y. K.; Shim, J. H.; Kim, M.; Han, M.; Livinghouse, T.; Lee, P. H. Adv. Synth. Catal. 2006, 348, 2609.
32. For asymmetric hydroamination using late metal catalysts, see: (a) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366.
33. (b) Paul, N. T.; Lutete, L. M.; Wu, H.; Pahadi, N. K.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2006, 71, 4270.
34. For examples of asymmetric hydroamination using other metal catalysts, see: (a) Knight, P. D.; Munslow, I.; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894.
35. (b) Gribkov, D. V.; Hultzcsh, K. C.; Angew. Chem., Int. Ed. 2004, 43, 5542.
36. (c) Martinez, P. H.; Hultzsch, K. C.; Hampel, F. Chem. Commun. 2006, 2221.
37. (d) Watson, D. A.; Chiu, M.; Bergman, R. G. Organometallics 2006, 25, 4731.
38. (e) Gott, A. L.; Clarke, A. J.; Clarkson, G. J.; Scott, P. Organometallics 2007, 26, 1729.
39. (a) Zi, G.-F.; Yin, C.-L. Acta Chim. Sin. 1998, 56, 484.
40. (b) Zi, G.-F.; Yin, C.-L. J. Mol. Catal. A: Chem. 1998, 132, L1.
41. (c) Zi, G.; Xiang, L.; Zhang, Y.; Wang, Q.; Yang, Y.; Zhang, Z. J. Organometal. Chem. 2007, 692, 3949.
42. (a) Zi, G.; Xiang, L.; Zhang, Y.; Wang, Q.; Zhang, Z. Appl. Organometal. Chem. 2007, 21, 177.
43. (b) Brown, K. J.; Berry, M. S.; Murdoch, J. R. J. Org. Chem. 1985, 50, 4345.
44. Bradley, D. C.; Ghotra, J. S.; Hart, F. A. J. Chem. Soc., Dalton Trans. 1973, 1021.
45. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1996.
46. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure from Diffraction Data; University of Göttingen: Göttingen, Germany, 1997.
47. For selected recent papers, see: (a) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4045.
48. (b) Hughes, A. K.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 1936.
49. (c) Carpenetti, D. W.; Kloppenburg, L.; Kupec, J. T.; Petersen, J. L. Organometallics 1996, 15, 1572.
50. (d) Zi, G.; Li, H.-W.; Xie, Z. Organometallics 2002, 21, 3580.
51. 2, see: Anwander, R.; Kumpel, M. G.; Martin Dietrich, H.; Shorokhov, D. J.; Scherer, W. Chem. Commun. 2003, 1008.
52. 3+ = 0.858 Å), see: Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 4th ed.; John Wiley & Sons: New York, 1980; p 982.
53. Yasuda, H. J. Polym. Sci., Polym. Chem. 2001, 39, 1955.
54. Lee, M.-H.; Hwang, J.-W.; Kim, Y.; Kim, J.; Han, Y.; Do, Y. Organometallics 1999, 18, 5124.
55. Zi, G.; Li, H.-W.; Xie, Z. Organometallics 2002, 21, 1136.
56. Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276.
57. Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
58. Jones, M. D.; Almeida Paz, F. A.; Davies, J. E.; Johnson, B. F. G. Acta Cryst. 2003, E59, o910.
59. Brady, E. D.; Clark, D. L.; Gordon, J. C.; Hay, P. J.; Keogh, D. W.; Poli, R.; Scott, B. L.; Watkin, J. G. Inorg. Chem. 2003, 42, 6682.
60. Westerhausen, M.; Hartmann, M.; Pfitzner, A.; Schwarz, W. Z. Anorg. Allg. Chem. 1995, 621, 837.
61. Freckmann, D. M. M.; Dubé, T.; Bérubé, C. D.; Gambarotta, S.; Yap, G. P. A. Organometallics 2002, 21, 1240.