Mechanism of the hydrogenation of ketones catalyzed by trans-dihydrido(diamine)ruthenium(II) complexes

Journal of the American Chemical Society

Volumn 124, Issue 50, 2002, Pages 15104-15118

  Abdur Rashid, Kamaluddin ^a   Clapham, Sean E ^a   Hadzovic, Alen ^a   Harvey, Jeremy N ^b   Lough, Alan J ^a   Morris, Robert H ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; BENZENE; CONCENTRATION (PROCESS); CRYSTALLOGRAPHY; HYDROGENATION; NITROGEN;

EQUATORIAL PLANE;

KETONES;

ACETOPHENONE; DIHYDRIDO(DIAMINE)RUTHENIUM; KETONE DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CATALYSIS; COMPLEX FORMATION; CONCENTRATION RESPONSE; GEOMETRY; HYDROGENATION; MOLECULAR INTERACTION; PRESSURE; PROTON TRANSPORT; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0037132617     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja016817p     Document Type: Article

References (65)

1. Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40-73.
2. Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931-7944.
3. Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285-288.
4. Casey, C. P.; Singer, S. W.; Powell, D. R.; Hayashi, R. K.; Kavana, M. J. Am. Chem. Soc. 2001, 123, 1090-1100.
5. Abdur-Rashid, K.; Lough, A. J.; Morris, R. H. Organometallics 2000, 19, 2655-2657.
6. Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580-9588.
7. Bernard, M.; Delbecq, F.; Sautet, P.; Fache, F.; Lemaire, M. Organometallics 2000, 19, 5715-5722.
8. Hartmann, R.; Chen, P. Angew. Chem., Int. Ed. 2001, 40, 3581-3585.
9. Abdur-Rashid, K.; Faatz, M.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2001, 123, 7473-7474.
10. Geoffroy, G. L. Inorganic and organometallic stereochemistry. In Topics in Stereochemistry, Vol. 12; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1981.
11. Abbel, R.; Abdur-Rashid, K.; Clapham, S.; Eberhardt, M.; Lough, A. J.; Morris, R. H., manuscript in preparation.
12. Chiu, W.-H.; Peng, S.-M.; Che, C.-M. Inorg. Chem. 1996, 35, 3369-3374.
13. Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163-1188.
14. Fryzuk, M. D.; Montgomery, C. D. Coord. Chem. Rev. 1989, 95, 1-40.
15. Fulton, J. R.; Holland, A. W.; Fox, D. J.; Bergman. R. G. Acc. Chem. Res. 2002, 35, 44-56.
16. Fulton, J. R.; Bouwkamp, M. W.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 8799-8800.
17. Basolo, F.; Pearson, R. G. Mechanisms of Inorganic Reactions; Wiley: New York, 1967.
18. Alcazar-Roman, L. M.; Hartwig, J. F.; Rheingold, A. L.; Liable-Sands, L. M.; Guzei, I. A. J. Am. Chem. Soc. 2000, 122, 4618-4630.
19. Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466-1478.
20. Aitali, M.; Allaoud, S.; Karim, A.; Meliet, C.; Mortreux, A. Tetrahedron: Asymmetry 2000, 11, 1367-1374.
21. Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199-1200.
22. Thorpe, T.; Blacker, J.; Brown, S. M.; Bubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043.
23. Mao, J.; Baker, D. C. Org. Lett. 1999, 1, 841-843.
24. Abdur-Rashid, K.; Lough, A. J.; Morris, R. H. Organometallics 2001, 20, 1047-1049.
25. Stevens, R. C.; Bau, R.; Milstein, D.; Blum, O.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1990, 1429-1432.
26. Lough, A. J.; Park, S.; Ramachandran, R.; Morris, R. H. J. Am. Chem. Soc. 1994, 116, 8356-8357.
27. Peris, E.; Lee, J. C.; Crabtree, R. H. J. Chem. Soc., Chem. Commun. 1994, 2573.
28. Also known as dihydrogen bonding, See articles in Recent Advances in Hydride Chemistry; Peruzini, M., Poli, R., Eds.; Elsevier: New York, 2001.
29. Schlaf, M.; Lough, A. J.; Morris, R. H. Organometallics 1996, 15, 4423-4436.
30. Schlaf, M.; Morris, R. H. J. Chem. Soc., Chem. Commun. 1995, 625-626.
31. Fan, H. J.; Hall, M. B. J. Biol. Chem. 2001, 6, 467-473.
32. Fan, H. J.; Hall, M. B. J. Am. Chem. Soc. 2001, 123, 3828-3829.
33. Fryzuk, M. D.; Montgomery, C. D.; Rettig, S. J. Organometallics 1991, 10, 467-473.
34. Morris, R. H. Inorg. Chem. 1992, 31, 1471-1478.
35. James, B. R.; Wang, D. K. W. Inorg. Chim. Acta 1976, 19, L17-L18.
36. Kaplan, A. W.; Ritter, J. C. M.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 6828-6829.
37. Lunder, D. M.; Lobkovsky, E. B.; Streib, W. E.; Caulton, K. G. J. Am. Chem. Soc. 1991, 113, 1837-1838.
38. Chin, B.; Lough, A. J.; Morris, R. H.; Schweitzer, C. T.; D'Agostino, C. Inorg. Chem. 1994, 33, 6278-6288.
39. Riehl, J. F.; Jean, Y.; Eisenstein, O.; Pélissier, M. Organometallics 1992, 11, 729-737.
40. Crabtree, R. H.; Siegbahn, P. E. M.; Eisenstein, O.; Rheingold, A. L. Acc. Chem. Res. 1996, 29, 348-354.
41. Abdur-Rashid, K.; Harvey, J. N.; Lough, A. J.; Morris, R. H., manuscript in preparation.
42. Pamies, O.; Backvall, J. Chem. Eur. J. 2001, 7, 5052-5058.
43. Solubility Data Series, Hydrogen and Deuterium, 5/6; Young, C. L., Ed., Pergamon Press: New York, 1981.
44. Solari, G.; Solari, E.; Floriani, C. Organometallics 1997, 16, 508-510.
45. Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816-5817.
46. Abdur-Rashid, K.; Fong, T. P.; Greaves, B.; Gusev, D. G.; Hinman, J. G.; Landau, S. E.; Morris, R. H. J. Am. Chem. Soc. 2000, 122, 9155-9171.
47. Navarro, M. E.; Chazaro, L. F.; Gonzalez, F. J.; Paz-Sandoval, M. A. J. Electroanal. Chem. 2000, 480, 18-25.
48. Bakhmutov, V. I.; Bakhmutova, E. V.; Belkova, N. V.; Bianchini, C.; Epstein, L. M.; Masi, D.; Peruzzini, M.; Shubina, E. S.; Vorontsov, E. V.; Zanobini, F. Can. J. Chem. 2001, 79, 479-489.
49. Belkova, N. V.; Ionidis, A. V.; Epstein, L. M.; Shubina, E. S.; Gruende-mann, S.; Golubev, N. S.; Limbach, H. H. Eur. J. Inorg. Chem. 2001, 1753-1761.
50. Messmer, A.; Jacobsen, H.; Berke, H. Chem. Eur. J. 1999, 5, 3341-3349.
51. Custelcean, R.; Jackson, J. E. Chem. Reu. 2001, 101, 1963-1980.
52. Belkova, N. V.; Shubina, E. S.; lonidis, A. V.; Epstein, L. M.; Jacobsen, H.; Messmer, A.; Berke, H. Inorg. Chem. 1997, 36, 1522-1525.
53. Ayllon, J. A.; Gervaux, C.; Sabo-Etienne, S.; Chaudret, B. Organometallics 1997, 16, 2000-2002.
54. Bautista, M. T.; Cappellani, E. P.; Drouin, S. D.; Morris, R. H.; Schweitzer, C. T.; Sella, A.; Zubkowski, J. J. Am. Chem. Soc. 1991, 113, 4876-4887.
55. Schlaf, M.; Lough, A. J.; Maltby, P. A.; Morris, R. H. Organometallics 1996, 15, 2270-2278.
56. Blum, O.; Milstein, D. J. Organomet. Chem. 2000, 593-594, 479-484.
57. Emerson, J.; Clarke, M. J.; Ying, W.-L.; Sanadi, D. R. J. Am. Chem. Soc. 1993, 115, 11799-11805.
58. Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754.
59. Safarowic, F. J.; Bierdeman, D. J.; Keister, J. B. J. Am. Chem. Soc 1996, 118, 11805-11812.
60. Cappellani, E. P.; Maltby, P. A.; Morris, R. H.; Schweitzer, C. T.; Steele, M. R. Inorg. Chem. 1989, 28, 4437-4438.
61. Bautista, M. T.; Earl, K. A.; Maltby, P. A.; Morris, R. H.; Schweitzer, C. T. Can. J. Chem. 1994, 72, 547-560.
62. Earl, K. A.; Jia, G.; Maltby, P. A.; Morris, R. H. J. Am. Chem. Soc. 1991, 113, 3027-3039.
63. Aranyos, A.; Csjernyik, G.; Szabo, K. J.; Backvall, J. E. Chem. Commun. 1999, 351-352.
64. Schrödinger, Inc., Portland, OR, 1996-2001.
65. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, 2000.