Synthesis and reactivity of platinum group metal complexes featuring the new pincer-like bis(phosphino)silyl ligand [K3-(2-Ph 2PC6H4)2SiMe]- ([PSiP]): Application in the ruthenium-mediated transfer hydrogenation of Ketones

Organometallics

Volumn 26, Issue 26, 2007, Pages 6522-6525

  MacInnis, Morgan C ^a   Maclean, Darren F ^a   Lundgren, Rylan J ^a   Mcdonald, Robert ^b   Turculet, Laura ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGENATION; LIGANDS; METAL COMPLEXES; PLATINUM COMPOUNDS; REACTION RATES; SYNTHESIS (CHEMICAL);

PINCER-TYPE COMPLEXES; PLATINUM GROUP METALS; RUTHENIUM-MEDIATED TRANSFER; SILYL LIGANDS;

ORGANOMETALLICS;

EID: 38049187394     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7009528     Document Type: Article

References (53)

1. (a) For selected recent examples and reviews see: Jensen, C. M. Chem. Commun. 1999, 2443.
2. b) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750.
3. (c) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
4. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837.
5. (e) Zhao, J.; Goldman, A. S.; Hartwig, J. F. Science 2005, 307, 1080.
6. (f) Goldman, A. S.; Roy, A. H.; Huang, Z.; Ahuja, R.; Schinski, W.; Brookhart, M. Science 2006, 312, 257.
7. For selected examples and reviews highlighting structural versatility see: (a) Fryzuk, M. D. Can. J. Chem. 1992, 70, 2839.
8. (b) Liang, L.-C. Coord. Chem. Rev. 2006, 250, 1152.
9. (c) Pugh, D.; Danopoulos, A. A. Coord. Chem. Rev. 2006, 251, 610.
10. (d) Gerisch, M.; Krumper, J. R.; Bergman, R. G.; Tilley, T. D. J. Am. Chem. Soc. 2001, 123, 5818.
11. (e) Lin, G.; Jones, N. D.; Gossage, R. A.; McDonald, R.; Cavell, R. G. Angew. Chem., Int. Ed. 2003, 42, 4054.
12. (f) Ozerov, O. V.; Guo, C.; Papkov, V. A.; Foxman, B. M. J. Am. Chem. Soc. 2004, 126, 4792.
13. (g) Yao, Q.; Sheets, M. J. Org. Chem. 2006, 71, 5384.
14. (h) Freeh, C. M.; Ben-David, Y.; Weiner, L.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 7128.
15. (i) Fischer, J.; Schürmann, M.; Mehring, M.; Zachwieja, U.; Jurkschat, K. Organometallics 2006, 25, 2886.
16. (j) Kuklin, S. A.; Sheloumov, A. M.; Dolgushin, F. M.; Ezernitskaya, M. G.; Peregudov, A. S.; Petrovskii, P. V.; Koridze, A. A. Organometallics 2006, 25, 5466.
17. (k) Weng, W.; Parkin, S.; Ozerov, O. Organometallics 2006, 25, 5345.
18. (l) Ma, L.; Imbesi, P. M.; Updegraff, J. B. III; Hunter, A. D.; Protasiewicz, J. D Inorg. Chem 2007, 46, 5220.
19. (m) Aydin, J.; Senthil Kumar, K.; Sayah, M. J.; Wallner, O. A.; Szabó, K. J. J. Org. Chem. 2007, 72, 4689.
20. (n) Guananathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790.
21. (a) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z. Eds.; Wiley: New York, 1991.
22. (b) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
23. (a) Balakrishna, M. S.; Chandrasekaran, P.; George, P. P. Coord. Chem. Rev. 2003, 241, 87.
24. (b) While the manuscript was in preparation, Fe complexes supported by a structurally related tetradentate tris(phosphino)silyl ligand were reported. Mankad, N. P.; Whited, M. T.; Peters, J. C. Angew. Chem., Int. Ed. 2007, 46, 5768.
25. (a) Auburn, M. J.; Stobart, S. R. Inorg. Chem. 1985, 24, 318.
26. (b) Joslin, F. L.; Stobart, S. R. J. Chem. Soc., Chem. Commun. 1989, 504.
27. (c) Auburn, M. J.; Holmes-Smith, R. D.; Stobart, S. R.; Bakshi, P. K.; Cameron, T. S. Organometallics 1996, 15, 3032.
28. (d) Gossage, R. A.; McLennan, G. D.; Stobart, S. R. Inorg. Chem. 1996, 35, 1729.
29. (e) Brost, R. D.; Bruce, G. C.; Joslin, F. L.; Stobart, S. R. Organometallics 1997, 16, 5669.
30. (f) Zhou, X.; Stobart, S. R. Organometallics 2001, 20, 1898.
31. (a) Stradiotto, M.; Fujdala, K. L.; Tilley, T. D. Chem. Commun. 2001, 1200.
32. (b) Sangtrirutnugul, P.; Stradiotto, M.; Tilley, T. D. Organometallics 2006, 25, 1607.
33. (c) Sangtrirutnugul, P.; Tilley, T. D. Organometallics 2007, 26, 5557.
34. A report on the use of phosphinoalkylsilyl metal complexes as catalysts for hydroformylation of olefins appears in the patent literature: Stobart, S. R.; Grundy, S. L.; Joslin, F. L. U.S. Patent 4,950,798, 1990; Canadian Patent 1,327,365, 1994.
35. 2 = 0.0975.
36. Bushnell, G. W.; Casado, M. A.; Stobart, S. R. Organometallics 2001, 20, 601.
37. (a) Thorn, D. L.; Hoffmann, R. New J. Chem. 1979, 3, 39.
38. (b) Riehl, J.-F.; Jean, Y.; Eisenstein, O.; Pelissier, M. Organometallics 1992, 11, 729.
39. (c) Chin, B.; Lough, A. J.; Morris, R. H.; Schweitzer, C. T.; D'Agostino, C. Inorg. Chem. 1994, 33, 6278.
40. (d) Johnson, T. J.; Folting, K.; Streib, W. E.; Martin, J. D.; Huffman, J. C.; Jackson, S. A.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 1995, 34, 488.
41. (e) Lam, W. H.; Shimada, S.; Batsanov, A. S.; Lin, Z.; Marder, T. B.; Cowan, J. A.; Howard, J. K.; Mason, S. A.; McIntyre, G. J. Organometallics 2003, 22, 4557.
42. PP = 16 Hz).
43. We attribute the 64% isolated yield of 3a to the conversion of 3b and/or 3c to 3a upon workup. Efforts to definitively identify 3b and 3c are ongoing.
44. (a) Gusev, D. G.; Dolgushin, F. M.; Antipin, M. Y. Organometallics 2000, 19, 3429.
45. (b) Amoroso, D.; Jabri, A.; Yap, G. P. A.; Gusev, D. G.; dos Santos, E. N.; Fogg, D. E. Organometallics 2004, 23, 4047.
46. (c) Zhang, J.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Milstein, D. Organometallics 2004, 23, 4026.
47. 2K in THF (COD = 1,5-cyclooctadiene). See: Fryzuk, M. D.; McConville, D. H.; Rettig, S. J. J. Organomet. Chem. 1993, 445, 245.
48. PP = 20 Hz).
49. (a) Dani, P.; Karlen, T.; Gossage, R. A.; Gladiali, S.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 743.
50. (b) Danopoulos, A. A.; Winston, S.; Motherwell, W. B. Chem. Commun. 2002, 1376.
51. (c) Baratta, W.; Chelucci, G.; Gladiali, S.; Siega, K.; Toniutti, M.; Zanette, M.; Zangrando, E.; Rigo, P. Angew. Chem., Int. Ed. 2005, 44, 6214.
52. (d) Weng, W.; Parkin, S.; Ozerov, O. Organometallics 2006, 25, 5345.
53. (e) Gagliardo, M.; Chase, P. A.; Brouwer, S.; van Klink, G. P. M.; van Koten, G. Organometallics 2007, 26, 2219.