Hydrogenation of aromatic ketones catalyzed by (η5-C5(CH3)5)Ru complexes bearing primary amines

Organometallics

Volumn 20, Issue 3, 2001, Pages 379-381

  Ito, Masato ^a   Hirakawa, Makoto ^a   Murata, Kunihiko ^a   Ikariya, Takao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINES; PROPANOL;

AMINES; AROMATIC COMPOUNDS; CATALYSIS; CATALYSTS; CHEMICAL ACTIVATION; COMPLEXATION; HYDROGENATION; ISOTOPES; KETONES;

RUTHENIUM COMPOUNDS;

EID: 0035809278     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000912+     Document Type: Article

References (66)

1. (a) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, pp 199-246.
2. (b) Blaser, H.-U.; Springer F. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, pp. 247-265.
3. (c) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; pp 16-94.
4. (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676.
5. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417-10418.
6. (c) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872-4873.
7. (d) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett, 1997, 467-468.
8. (e) Ohkuma, T.; Doucet, T.; Pham, K.; Mikami, T.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 0, 1086-1087.
9. (f) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703-1707.
10. (g) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529-13530.
11. (h) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497.
12. (i) Noyori, R.; Ohkuma, T. Pure. Appl. Chem. 1999, 71, 1493-1501.
13. (j) Ohkuma, T.; Koizumi, M.; Ikehara, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662.
14. (k) Ohkuma, T.; Koizumi, M.; Yoshida, M.; Noyori, R. Org. Lett. 2000, 2, 1749-1751.
15. (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562-7563.
16. (b) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
17. (c) Uematsu, N.; Fujii, A.; Hashigushi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916-4917.
18. (d) Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285-288.
19. (e) Hashiguchi, S.; Fujii, A.; Haack, K.-J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288-290.
20. (f) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
21. (g) Noyori, R.; Hashiguchi. S. Acc. Chem. Res. 1997, 30, 97-102.
22. (h) Murata, K.; Okano, K.; Miyagi, M.; Iwane, H.; Noyori, R; Ikariya, T. Org. Lett. 1999, 1, 1119-1121.
23. (i) Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466-1478.
24. Catalytic asymmetric reduction of ketones or imines using transition metal complexes bearing NH ligands. For Ru, see: (a) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233-234.
25. (b) Gao, J.-X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087-1089.
26. (c) Püntener, K.; Schwink, L.; Knochel, P. Tetrahedron Lett. 1996, 37, 8165-8168.
27. (d) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 6565-6568.
28. (e) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
29. (f) Ohta, T.; Nakahara, S.; Shigemura, Y.; Hattori, K.; Furukawa, I. Chem. Lett. 1998, 491-492.
30. (g) Alonso, D. A.; Guijarro, D.; Pinho, P.; Temme, O.; Anderson, P. G. J. Org. Chem. 1998, 63, 2749-2751.
31. (h) Jiang, Y.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1998, 120, 3817-3818.
32. (i) Schwick, L.; Ireland, T.; Püntener, K.; Knochel, P. Tetrahedron: Asymmetry 1998, 9, 1143-1163.
33. (j) Everaere, K.; Carpenter, J.-F.; Mortreux, A.; Bulliard, M. Tetrahedron: Asymmetry 1998, 9, 2971-2974.
34. (k) Alonso, D. A; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580-9588.
35. (l) Abdur-Rashid, K.; Lough, A. J.; Morris, R. H. Organometallics 2000, 19, 2655-2657.
36. For other metals; see: (m) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897-6898.
37. (n) Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. J. Chem. Soc., Chem. Commun. 1994, 1417-1418.
38. (o) Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry. 1995, 6, 705-718.
39. (p) Gamez, P.; Dunjic, B.; Lemaire, M. J. Org. Chem. 1996, 61, 5196-5197.
40. (q) ter Halle, R.; Bréhéret, A.; Schluz, E.; Pinel, C.; Lemaire, M. Tetrahedron: Asymmetry 1997, 8, 2101-2108.
41. (r) Touchard, F.; Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron Lett. 1997, 38, 2275-2278.
42. (s) Touchard, F.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1997, 8, 3319-3326.
43. (t) Bernard, M.; Guiral, V.; Delbecq, F.; Fache, F.; Sautet, P.; Lemaire, M. J. Am. Chem. Soc. 1998, 120, 1441-1446.
44. (u) Inoue, S.; Nomura, K.; Hashiguchi, S.; Noyori, R.; Izawa, Y. Chem. Lett. 1997, 957-958.
45. (v) Stinson, S. C. Chem. Eng. News 1998, 76, 6(22), 15-24.
46. (w) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199-1200.
47. (x) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1201-1202.
48. (y) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186-2187.
49. (z) Mao, J.; Baker, D. C. Org. Lett. 1, 841-843.
50. Oshima, N.; Suzuki, H.; Moro-oka, Y. Chem. Lett. 1984, 1161-1164.
51. Fagan, P. J.; Ward, M. D.; Calabrese, J. C. J. Am. Chem. Soc. 1989, 111, 1698-1719
52. Koelle, U. Chem. Rev. 1998, 98, 1313-1334.
53. Inagaki, A.; Takemori, T.; Tanaka, M.; Suzuki, H. Angew. Chem., Int. Ed. 2000, 39, 404-406, and references therein.
54. Chemistry on transition metal dihydrogen complexes, see: (a) Kubas, G. J. Acc. Chem. Res. 1988, 21, 120-128.
55. (b) Crabtree, R. H. Acc. Chem. Res. 1990, 23, 95-101.
56. (c) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 155-284.
57. (d) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913-926.
58. (e) Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1993, 32, 789-805.
59. (f) Esteruelas, M. A.; Oro, L. A. Chem. Rev. 1998, 98, 577-588.
60. For reviews on the MH- - -HX (M = transition metal, X = N, O) interaction (dihydrogen bonding), see: (a) Crabtree, R. H.; Siegbahn, P. E. M.; Eisenstein, O.; Rheingold, A. L.; Koetzle, T. Acc. Chem. Res. 1996, 29, 348-354.
61. (b) Shubina, E. S.; Belkova, N. V.; Epstein, L. M. J. Organomet. Chem. 1997, 536-537, 17-29.
62. (c) Crabtree, R. H. Science 1998, 282, 2000-2001.
63. 2 and alcoholic OH. Guari, Y.; Ayllon, J. A; Sabo-Etienne, S.; Chaudret, B.; Hessen, B. Inorg. Chem. 1998, 37, 640-644.
64. Grundemann, S.; Ulrich, S.; Limbach, H.-H.; Golubev, N. S.; Denisov, G. S.; Epstein, L. M.; Sabo-Etienne, S.; Chaudret, B. Inorg. Chem. 1999, 38, 2550-2551, and references therein.
65. Chan, W. C.; Lau, C. P.; Chen, Y. Z.; Fang, Y. Q.; Ng, S. M.; Jia, G. Organometallics 1997, 16, 34-44.
66. Lau, C. P.; Cheng, L. Inorg. Chem. Acta 1992, 195, 133-134, and references therein.