The first Ru(ν 3-PCP) complexes of the electron-rich pincer ligand l,3-bis((dicyclohexylphosphino)methyl)benzene: Structure and mechanism in transfer hydrogenation catalysis

Organometallics

Volumn 23, Issue 17, 2004, Pages 4047-4054

  Amoroso, Dino ^a,b   Jabri, Amir ^a   Yap, Glenn P A ^a   Gusev, Dmitry G ^a,c   Dos Santos, Eduardo N ^a,d   Fogg, Deryn E ^a,b  

^a UNIVERSITY OF OTTAWA   (Canada)

^b Promerus LLC   (United States)

^c WILFRID LAURIER UNIVERSITY   (Canada)

^d FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

DEPROTONATION; LIGANDS; TRANSFER HYDROGENATION;

BENZENE; CATALYSIS; COMPLEXATION; CONFORMATIONS; CRYSTAL STRUCTURE; HYDROGENATION; ISOMERS; KETONES; ORGANOMETALLICS; X RAY CRYSTALLOGRAPHY;

RUTHENIUM COMPOUNDS;

EID: 4344568089     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om040025x     Document Type: Article

References (56)

1. Albrecht, M.; Kocks, B. M.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 2001, 624, 271.
2. Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750.
3. van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
4. Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798.
5. Jensen, C. M. J. Chem. Soc., Chem. Commun. 1999, 2243.
6. Milstein, D. Pure Appl. Chem. 2003, 75, 445.
7. van de Kuil, L. A.; Grove, D. M.; Gossage, R. A.; Zwikker, J. W.; van Koten, G. Organometallics 1997, 16, 4985.
8. Gossage, R. A.; van de Kuil, L. A.; van Koten, G. Acc. Chem. Res. 1998, 31, 428.
9. del Rio, I.; van Koten, G. Tetrahedron Lett. 1999, 40, 1401.
10. (a) Gusev, D. G.; Madott, M.; Dolgushin, F. M.; Lyssenko, K. A.; Antipin, M. Y. Organometallics 2000, 19, 1734.
11. (b) Gusev, D. G.; Dolgushin, F. M.; Antipin, M. Y. Organometallics 2000, 19, 3429.
12. (a) Gusev, D. G.; Maxwell, T.; Dolgushin, F. M.; Lyssenko, M.; Lough, A. J. Organometallics 2002, 21, 1095.
13. (b) Reinhart, B.; Gusev, D. G. New J. Chem. 1999, 23, 1.
14. Farrington, E. J.; Viviente, E. M.; Williams, B. S.; van Koten, G.; Brown, J. M. J. Chem. Soc., Chem. Commun. 2002, 308.
15. van der Boom, M. E.; Kraatz, H.-B.; Hassner, L.; Ben-David, Y.; Milstein, D. Organometallics 1999, 18, 3873.
16. (a) Cross, R. J.; Kennedy, A. R.; Muir, K. W. J. Organomet. Chem. 1995, 487, 227.
17. (b) Cross, R. J.; Kennedy, A. R.; ManojlovicMuir, L.; Muir, K. W. J. Organomet. Chem. 1995, 493, 243.
18. (c) Kennedy, A. R.; Cross, R. J.; Muir, K. W. Inorg. Chim. Acta 1995, 237, 207.
19. (d) Kennedy, A. R.; Cross, R. J.; Muir, K. W. Inorg. Chim. Ada 1995, 231, 195.
20. Drouin, S. D.; Amoroso, D.; Yap, G. P. A.; Fogg, D. E. Organometallics 2002, 21, 1042.
21. (a) Yun, J. G.; Seul, J. M.; Lee, K. D.; Kim, S.; Park, S. Bull. Korean Chem. Soc. 1996, 17, 311.
22. (b) Ryu, S. Y.; Yang, W.; Kim, H. S.; Park, S. Bull. Korean Chem. Soc. 1997, 18, 1183.
23. (c) Park, S. Bull. Korean Chem. Soc. 2000, 21, 1251.
24. (d) Park, S. Bull. Korean Chem. Soc. 2002, 23, 132.
25. (e) Seul, J. M., Park, S. J. Chem. Soc., Dalion Trans. 2002, 1163.
26. Amoroso, D.; Snelgrove, J. L.; Conrad, J. C.; Drouin, S. D.; Yap, G. P. A.; Fogg, D. E. Adv. Synth. Catal. 2002, 344, 757.
27. Gusev, D. G. Personal communication.
28. Karlen, T.; Dani, P.; Grove, D. M.; Steenwinkel, P.; van Koten, G. Organometallics 1996, 15, 5687.
29. (a) Jia, G.; Lee, H. M.; Xia, H. P.; Williams, I. D. Organometallics 1996, 15, 5453.
30. (b) Jia, G.; Lee, H. M.; Williams, I. D. J. Organomet, Chem. 1997, 534, 173.
31. Vigalok, A.; Uzan, O.; Shimon, L. J. W.; Ben-David, Y.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 12539.
32. (a) Crocker, C.; Errington, R. J.; McDonald, W. S.; Odell, K. J.; Shaw, B. L.; Goodfellow, R. J. J. Chem. Soc., Chem. Commun. 1979, 498
33. (b) Crocker, C.; Errington, R. J.; Markham, R.; Moulton, C. J.; Odell, K. J.; Shaw, B. L. J. Am. Chem. Soc. 1980, 102, 4373.
34. Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867.
35. The high trans influence of hydride is manifested in a strong site preference: this ligand normally takes up the apical site in square pyramidal complexes, for which these diagnostic upfield chemical shifts are observed. See, for example: Marchenko, A. V.; Huffman, J. C.; Valerga, P.; Tenorio, M. J.; Puerta, M. C.; Caulton, K. G. Inorg. Chem. 2001, 40, 6444.
36. Amoroso, D.; Yap, G. P. A.; Fogg, D. E. Can. J. Chem. 2001, 79, 958.
37. Kubas, G. J., Ed. Metal Dihydrogen and σ-Bond. Complexes. Structure, Theory and Reactivity; Kluwer Academic/Plenum Publishers: New York, 2001.
38. One cyclohexyl group was also conformationally disordered, with a 50/50 site occupancy distribution.
39. In complex 6, the remaining carbonyl and chloride ligands are disordered; the electron density is distributed over C(34), O(2), and Cl(1) and the positions are arbitrarily assigned. The excess of electron density at C(34) results in an unusually small ellipsoid.
40. Hidai, M.; Mizobe, Y. Chem. Rev. 1995, 95, 1115.
41. Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. Organometallics 1996, 15, 1793.
42. Gottschalk-Gaudig, T.; Folting, K.; Caulton, K. G. Inorg. Chem. 1999, 38, 5241.
43. Batista, A. A.; Zukerman-Schpector, J.; Porcu, O. M.; Queiroz, S. L.; Araujo, M. P.; Oliva, G.; Souza, D. H. F. Polyhedron 1994, 13, 689.
44. Wilkes, L. M.; Nelson, J. H.; Mitchener, J. P.; Babich, M. W.; Riley, W. C.; Helland, B. J.; Jacobson, R. A.; Cheng, M. Y.; Seff, K.; McCusker, L. Inorg. Chem. 1982, 21, 1376.
45. Dani, P.; Karlen, T.; Gossage, R. A.: Gladiali, S.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 743.
46. Aranyos, A.; Csjernyik, G.; Szabó, K. J.; Bäckvall, J.-E. J. Chem. Soc., Chem. Commun. 1999, 351.
47. Chowdhury, R.; Bäckvall, J.-E. J. Chem. Soc., Chem. Commun. 1991, 1063.
48. Morton, D.; Cole-Hamilton, D. J. J. Chem. Soc., Chem. Commun. 1988, 1154.
49. Berkessel, A.; Schubert, T. J. S.; Mueller, T. N. J. Am. Chem. Soc. 2002, 124, 8693.
50. Walling, C.; Bollyky, L. J. Am. Chem. Soc. 1964, 86, 3750.
51. Bäckvall, J.-E. J. Organomet. Chem. 2002, 652, 105.
52. LePage, M. D.; James, B. R. J. Chem. Soc., Chem. Commun. 2000, 1647.
53. While the presence of base can trigger aldol condensation of ketones, only traces of heavier byproducts (<1%) were observed even over the combined time scale of pretreatment and reduction experiments (ca. 3.5 h), reaching 3% after 19 h.
54. Hallman, P. S.; Stephenson, T. A.; Wilkinson, G. Inorg. Synth. 1970, 12, 237.
55. Blessing, R. Acta Crystallogr. 1995, A51, 33-38.
56. Sheldriok, G. M. SHELXTL 6.12; Bruker AXS: Madison, WI, 2001.