Multifunctional ruthenium catalysts: A novel borohydride-stabilized polyhydride complex containing the basic, chelating diphosphine 1,4-bis(dicyclohexylphosphino)butane and its application to hydrogenation and Murai catalysis

Organometallics

Volumn 21, Issue 6, 2002, Pages 1042-1049

  Drouin, Samantha D ^a   Amoroso, Dino ^a   Yap, Glenn P A ^a   Fogg, Deryn E ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MURAI CATALYSIS;

CATALYSIS; CATALYSTS; COMPLEXATION; HYDRIDES; HYDROGENATION; ORGANOMETALLICS; SOLUBILITY; X RAY CRYSTALLOGRAPHY;

RUTHENIUM;

EID: 0012665293     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010745t     Document Type: Article

References (63)

1. Recent reviews: (a) General Ru catalysis: Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
2. (b) C-C bond activation: Mitsudo, T.-A.; Kondo, T. Synlett 2001, 309.
3. (c) Kharasch and atom transfer radical polymerization: Simal, F.; Demonceau, A.; Noels, A. F. Recent Res. Dev. Org. Chem. 1999, 3 (Pt. 2), 455.
4. (d) Biomimetic oxidations: Murahashi, S.-I.; Naruyoshi, K. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; p 563.
5. (e) Lewis acid and base catalysis: Murahashi, S. I.; Takaya, H. Acc. Chem. Res. 2000, 33, 225.
6. (f) Olefin metathesis: Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
7. (g) Oxidation of alcohols: Friedrich, H. B. Platinum Met. Rev. 1999, 43, 94.
8. (h) Epoxidation and aziridination of alkenes: Che, C.-M.; Yu, W.-Y. Pure Appl. Chem. 1999, 71, 281.
9. (i) Oxidative dehalogenation of organics: Bressan, M.; d'Alessandro, N.; Liberatore, L.; Morvillo, A. Coord. Chem. Rev. 1999, 185-186, 385.
10. (j) Murai catalysis: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
11. (k) Asymmetric reduction of ketones: Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
12. (l) Copolymerization of aromatic ketones and 1,3-divinyltetramethyldisiloxane: Weber, W. P.; Guo, H.; Kepler, C. L.; Londergan, T. M.; Lu, P.; Paulsaari, J.; Sargent, J. R.; Tapsak, M. A.; Wang, G. ACS Symp. Ser. 2000, No. 729, 433.
13. (m) C-C bond formation (nonmetathesis): Trost, B. M.; Toste, D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
14. (a) Burk, M. J.; Martinez, J. P.; Feaster, J. E.; Cosford, N. Tetrahedron 1994, 50, 4399.
15. (b) Burk, M. J. Acc. Chem. Res. 2000, 33, 363.
16. Amoroso, D.; Fogg, D. E. Macromolecules 2000, 33, 2815.
17. Amoroso, D.; Yap, G. P. A.; Fogg, D. E. Can. J. Chem. 2001, 79, 958.
18. Six, C.; Beck, K.; Wegner, A.; Leitner, W. Organometallics 2000, 19, 4639.
19. (a) Volland, M. A. O.; Straub, B. F.; Gruber, I.; Rominger, F.; Hofmann, P. J. Organomet. Chem. 2001, 617, 288.
20. (b) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisentrager, F.; Hofmann, P. Angew. Chem., Int. Ed. 1999, 38, 1273.
21. (a) Drouin, S. D.; Yap, G. P. A.; Fogg, D. E. Inorg. Chem. 2000, 39, 5412.
22. (b) Drouin, S. D.; Zamanian, F.; Fogg, D. E. Organometallics 2001, 20, 5495.
23. (c) Fogg, D. E.; Drouin, S. D.; Zamanian, F. U.S. Pat. Appl. 09/816,571, priority date March 26, 2000.
24. (a) Murai, S.; Chatani, N.; Kakiuchi, F. Pure Appl. Chem. 1997, 69, 589.
25. (b) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62.
26. Via use of hydride as a synthon for alkylidene: Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867.
27. Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659.
28. James, B. R.; Markham, L. D.; Hui, B. C.; Rempel, G. L. J. Chem. Soc., Dalton Trans. 1973, 2247.
29. Gottschalk-Gaudig, T.; Folting, K.; Caulton, K. G. Inorg. Chem. 1999, 38, 5241.
30. 3 molecule (see text).
31. Gusev, D. G.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 1998, 120, 13138.
32. Huffman, J. C.; Green, M. A.; Kaiser, S. L.; Caulton, K. G. J. Am. Chem. Soc. 1985, 107, 5111.
33. Yandulov, D. V.; Huang, D.; Huffman, J. C.; Caulton, K. G. Inorg. Chem. 2000, 39, 1919 and references therein.
34. Fordyce, W. A.; Wilczynski, R.; Halpern, J. J. Organomet. Chem. 1985, 296, 115.
35. (a) Leitner, W.; Six, C. Chem. Ber. 1997, 130, 555.
36. (b) Six, C.; Gabor, B.; Gorls, H.; Mynott, R.; Philipps, P.; Leitner, W. Organometallics 1999, 18, 3316.
37. (a) Christ, M. L.; Sabo-Etienne, S.; Chaudret, B. Organometallics 1995, 14, 1082.
38. (b) Borowski, A.; Sabo-Etienne, S.; Christ, M. L.; Donnadieu, B.; Chaudret, B. Organometallics 1996, 15, 1427.
39. Chan, A. S. C.; Shieh, H. S. J. Chem. Soc., Chem. Commun. 1985, 1379.
40. Marks, T. J.; Kolb, J. Chem. Rev. 1977, 77, 263.
41. Darensbourg, M. Y.; Ash, C. E. Adv. Organomet. Chem. 1987, 27, 1.
42. Pez, G. P.; Grey, R. A.; Corsi, J. J. Am. Chem. Soc. 1981, 103, 7528.
43. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97 and references therein.
44. (a) Halpern, J. Pure Appl. Chem. 1987, 59, 173
45. (b) Linn, D. E.; Halpern, J. J. Organomet. Chem. 1987, 330, 155.
46. Kelson, E. P.; Phengsy, P. P. J. Chem. Soc., Dalton Trans. 2000, 4023.
47. Dani, P.; Karlen, T.; Gossage, R. A.; Gladiali, S.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 743.
48. Crochet, P.; Gimeno, J.; Garcia-Granda, S.; Borge, J. Organometallics 2001, 20, 4369.
49. (a) Matsubara, T.; Koga, N.; Musaev, D. G.; Morokuma, K. Organometallics 2000, 19, 2318.
50. Matsubara, T.; Koga, N.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 12692.
51. Guari, Y.; Sabo-Etienne, S.; Chaudret, B. J. Am. Chem. Soc. 1998, 120, 4228.
52. Busch, S.; Leitner, W. Adv. Synth. Catal. 2001, 343, 192.
53. 3 CO, DMSO) was published: Jazzar, R. F. R.; Mahon, M. F.; Whittlesey, M. K. Organometallica 2001, 20, 3745. In contrast to the behavior of 5, the CO derivative was found to be completely inactive for Murai coupling. X-ray structural characterization of this complex locates the hydride ligand in the Ru-O-C(aryl) plane (cf. the structure of 5 in Figure 3).
54. Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141.
55. Dauter, Z.; Mawby, R. J.; Reynolds, C. D.; Saunders, D. R. J. Chem. Soc., Dalton Trans. 1985, 1235.
56. Yi, C. S.; Lee, D. W.; Chen, Y. Organometallics 1999, 18, 2043.
57. Ahmad, N.; Levison, J. J.; Robinson, S. D.; Uttley, M. F. In Inorganic Syntheses; Parshall, G. W., Ed.; McGraw-Hill: New York, 1974; Vol. 15, p 45.
58. McGuiggan, M. F.; Pignolet, L. H. Inorg. Chem. 1982, 21, 2523.
59. Chau, D. E. K. Y. M.Sc. Thesis, University of British Columbia, 1992.
60. DeRoos, A. M. Recl. Trav. Chim. Pays-Bas 1968, 87, 1381.
61. Moers, F. G.; Hoedt, R. W. M. T.; Langhout, J. P. J. Organomet. Chem. 1974, 65, 93.
62. Blessing, R. Acta Cryatallogr. 1995, A51, 33.
63. Sheldrick, G. M. SHELXTL V5.10; Siemens Analytical X-ray Instruments. Inc., Madison, WI, 1997.