Hydrogen transfer to ketones catalyzed by Shvo's ruthenium hydride complex: A mechanistic insight

Organometallics

Volumn 26, Issue 17, 2007, Pages 4135-4144

  Comas Vives, Aleix ^a   Ujaque, Gregori ^a   Lledós, Agustí ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; COMPLEXATION; HYDROGENATION; REACTION KINETICS; RUTHENIUM COMPOUNDS;

HYDROGEN TRANSFER; MECHANISTIC INVESTIGATIONS; RUTHENIUM HYDRIDE COMPLEXES; SHVO CATALYSTS;

ORGANOMETALLICS;

EID: 34548191521     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7004832     Document Type: Article

References (83)

1. Clarke, M. L.; Roff, G. J. In Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, 2007; Vol. 1, p 413.
2. For reviews see: (a) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226-236.
3. (b) Samec, J. S. M.; Bäckvall, J.-E.; Andersson, P. G.; Brant, P. Chem. Soc. Rev. 2006, 35, 237-248.
4. (c) Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201-2237.
5. (d) Bäckvall, J.-E. J. Organomet. Chem. 2002, 652, 105-111.
6. (e) Noyori, R.; Hashiguchi, R. Acc. Chem. Res. 1997, 30, 97-102.
7. (f) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051-1069.
8. (a) Noyori, R.; Ohkuma, T. Angew. Chem. 2001, 113, 40-75;
9. Angew. Chem., Int. Ed. 2001, 40, 40-73.
10. (b) Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490-13503.
11. (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
12. (d) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916-4917.
13. (a) Bullock, R. M. Chem. - Eur. J. 2004, 10, 2366-2374.
14. (b) Guan, H.; Iimura, M.; Magee, M. P.; Norton, J. R.; Zhu, G. J. Am. Chem. Soc. 2005, 127, 7805-7814.
15. (a) Blum, Y.; Czarkie, D.; Rahamim, Y.; Shvo, Y. Organometallics 1985, 4, 1459-1461.
16. (b) Shvo, Y.; Czarkie, D.; Rahamim, Y. J. Am. Chem. Soc. 1986, 108, 7400-7402.
17. Karvembu, R.; Prabhakaran, R.; Natarajan, K. Coord. Chem. Rev. 2005, 249, 911-918.
18. Shvo, Y.; Goldberg, I.; Czierkie, D.; Reshef, D.; Stein, Z. Organometallics 1997, 16, 133-138.
19. Menashe, N.; Salant, E.; Shvo, Y. J. Organomet. Chem. 1996, 514, 97-102.
20. Samec, J. S. M.; Bäckvall, J.-E. Chem.-Eur. J. 2002, 5, 2955-2961.
21. Csjernyk, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657-1662.
22. (a) Samec, J. S. M.; Éll, A. H.; Bäckvall, J.-E. Chem.-Eur. J. 2005, 11, 2327-2334.
23. (b) Éll, A. H.; Samec, J. S. M.; Brasse, C.; Bäckvall, J.-E. Chem. Commun. 2002, 1144-1145.
24. (a) Larsson, A. L. E.; Persson, B. A.; Bäckvall, J.-E. Angew. Chem. 1997, 109, 1256-1258;
25. Angew. Chem., Int. Ed. 1997, 36, 1211-1212.
26. (b) Persson, B. A.; Larsson, A. L. E.; Ray, M. L.; Bäckvall, J.-E. J. Am. Chem. Soc. 1999, 121, 1645-1650.
27. Paetzold, J.; Bäckvall, J.-E. J. Am. Chem. Soc. 2005, 127, 17620-17621.
28. (a) Gómez, M.; Jansat, S.; Muller, G.; Aullón, G.; Maestro, M. A. Eur. J. Inorg. Chem. 2005, 4341-4351.
29. (b) Ito, M.; Hirakawa, M.; Murata, K.; Ikariya, T. Organometallics 2001, 20, 379-381.
30. (c) Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104-15118.
31. (a) Wu, X.; Vinci, D.; Ikariya, T.; Xiao, J. Chem. Commun. 2005, 4447-4449.
32. (b) Clapham, S. E.; Morris, R. H. Organometallics, 2005, 24, 479-481.
33. (c) Mao, J.; Baker, D. C. Org. Lett. 1999, 1, 841-843.
34. (d) Martin, M.; Sola, E.; Tejero, S.; Andres, J. L.; Oro, L. A Chem.-Eur. J. 2006, 12, 4043-4056.
35. Casey, C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am. Chem. Soc. 2005, 127, 3100-3109.
36. Rautenstrauch, V.; Hoang-Cong, X.; Churlaud, R.; Abdur-Rashid, K.; Morris, R. H. Chem.-Eur. J. 2003, 9, 4954-4967.
37. Hedberg, C.; Källström, K.; Arvidsson, P. I.; Brandt, P.; Andersson, P. G. J. Am. Chem. Soc. 2005, 127, 15083-15090.
38. Comas-Vives, A.; González-Arellano, C.; Corma, A.; Iglesias, M.; Sánchez, F.; Ujaque, G. J. Am. Chem. Soc. 2006, 128, 4756-4765.
39. Casey, C. P.; Singer, S.W.; Powell, D. R.; Hayashi, R. K.; Kavana, M. J. Am. Chem. Soc. 2001, 123, 1090-1100.
40. Casey, C. P.; Bikzhanova, G. A.; Cui, Q.; Guzei, I. A. J. Am. Chem. Soc. 2005, 127, 14062-14071 (see also Supporting Information therein).
41. Johnson, J. B.; Bäckvall, J.-E. J. Org. Chem. 2003, 68, 7681-7684.
42. (a) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657-1662.
43. (b) In ref 7 Shvo proposed the same ring slippage for alkyne hydrogenation.
44. (a) Casey, C. P.; Bikzhanova, G. A.; Guzei, I. A. J. Am. Chem. Soc. 2006, 128, 2286-2293.
45. (b) Casey, C. P.; Johnson, J. B. J. Am. Chem. Soc. 2005, 127, 1883-1894.
46. (a) Samec, J. S. M.; Éll, A. H.; Bäckvall, J.-E. Chem. Commun. 2004, 2748-2749.
47. (b) Éll, A. H.; Johnson, J. B.; Bäckvall, J.-E. Chem. Commun. 2003, 1652-1653.
48. Samec, J. S. M.; Éll, A. H.; Âberg, J. B.; Privalov, T.; Eriksson, L.; Bäckvall, J.-E. J. Am. Chem. Soc. 2006, 128, 14293-14305.
49. Casey, C. P.; Bikzhanova, G. A.; Bäckvall, J.-E.; Johansson, L.; Park, J.; Kim, Y. H. Organometallics 2002, 21, 1955-1959.
50. (a) Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466-1478.
51. (b) Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998-2001.
52. (c) Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580-9588.
53. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
54. Frisch, M. J.; et al. Gaussian03; Gaussian, Inc.: Wallingford, CT, 2004.
55. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
56. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
57. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
58. (a) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622.
59. (b) Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503-506.
60. (c) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 275-280.
61. (d) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 281-289.
62. (e) Head-Gordon, M.; Head-Gordon, T. Chem. Phys. Lett. 1994, 220, 122-128.
63. (f) Sæbø, S.; Almlöf, J. Chem. Phys. Lett. 1989, 154, 83-89.
64. (a) Cizek, J. Adv. Chem. Phys. 1969, 14, 35-89.
65. (b) Purvis G. D., III; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918.
66. (c) Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387.
67. (d) Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
68. (e) Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968-5975.
69. Jaguar 5.5; Schrödinger, L.L.C.: Portland, OR, 1991-2003.
70. (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001.
71. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681.
72. 2, see for instance: (a) Bergamo, M.; Beringhelli, T.; D'Alfonso, G.; Maggioni, D.; Mercandelli, P.; Sironi, A. Inorg. Chim. Acta 2003, 350, 475-485.
73. (b) Méndez, N. Q.; Arif, A. M.; Gladysz, J. A. Angew. Chem., Int. Ed. 1990, 29, 1473-1474.
74. (c) Méndez, N. Q.; Mayne, C. L.; Gladysz, J. A. Angew. Chem., Int. Ed. 1990, 29, 1475-1476.
75. (d) Méndez, N. Q.; Seyler, J. W.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 2323-2334.
76. (e) Boone, B. J.; Klein, D. P.; Seyler, J. W.; Méndez, N. Q.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1996, 118, 2411-2421.
77. Veiros, L. F. Organometallics 2000, 19, 5549-5558.
78. Fan, H.-J.; Hall, M. B. Organometallics 2001, 20, 5724-5730.
79. (a) Fukui, K. Acc. Chem. Res. 1981, 14, 363-368.
80. (b) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
81. (c) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
82. Casey, C. P.; Johnson, J. B. Can. J. Chem. 2005, 83, 1339.
83. The transition state ts1d2 (for the complete system) was recalculated with Gaussian03. The geometries and energies obtained are very similar. The energy barriers found here were 8.3 and 8.0 kcal/mol in the gas phase and in solution, respectively.