A bowl-shaped phosphine as a ligand in rhodium-catalyzed hydrosilylation: Rate enhancement by a mono(phosphine) rhodium species

Organometallics

Volumn 24, Issue 14, 2005, Pages 3468-3475

  Niyomura, Osamu ^a,b   Iwasawa, Tetsuo ^a   Sawada, Naoki ^a   Tokunaga, Makoto ^a   Obora, Yasushi ^a   Tsuji, Yasushi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ENVIRONMENT; LIGANDS; PHOSPHINES; REACTANTS;

CATALYSIS; COMPLEXATION; MOLECULAR STRUCTURE; ORGANOMETALLICS; RHODIUM COMPOUNDS; SILANES; TRANSITION METALS; X RAY ANALYSIS;

CHELATION;

EID: 22444436384     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0503491     Document Type: Article

References (47)

1. (a) Homogeneous Catalysis with Metal Phosphine Complexes; Pignolet, L. H., Ed.; Plenum: New York, 1983.
2. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Applications of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1999.
3. (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
4. (b) Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.
5. (c) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
6. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5556.
7. (e) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871-1876.
8. (a) Maverick, E.; Cram, D. J. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Elsevier: Oxford, U.K., 1996; Vol. 2, pp 367-418.
9. (b) Goto, K.; Okumura, T.; Kawashima, T. Chem. Lett. 2001, 1258-1259.
10. (c) Goto, K.; Nagahama, M.; Mizushima, T.; Shimada, K.; Kawashima, T.; Okazaki, R. Org. Lett. 2001, 3, 3569-3572.
11. (d) Naiki, M.; Shirakawa, S.; Kon-i, K.; Kondo, Y.; Maruoka, K. Tetrahedron Lett. 2001, 42, 5467-5471.
12. (e) Ohzu, Y.; Goto, K.; Kawashima, T. Angew. Chem., Int. Ed. 2003, 42, 5714-5717.
13. (a) Goto, K.; Ohzu, Y.; Sato, H.; Kawashima, T. Abstr. Pap. 15th Int. Conf. Of Phosphorous Chemistry (Sendai, Japan) 2001, 236.
14. (b) Goto, K.; Ohzu, Y.; Sato, H.; Kawashima, T. Phosphorus, Sulfur, Silicon Relat. Elem. 2002, 177, 2179.
15. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
16. (a) Goto, H. J. Am. Chem. Soc. 1989, 111, 8950-8951.
17. (b) Lii, J.-H. Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566-8575.
18. (c) Lii, J.-H. Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576-8582.
19. Recently we prepared pyridine ligands bearing a 2,3,4,5-tet- raphenylphenyl moiety at the 3-position. The pyridine ligands have steric congestion at remote positions from the coordination center (nitrogen). This "long-range steric effect" of the pyridine ligands successfully suppresses Pd black formation in air oxidation of alcohols: Iwasawa, T.; Tokunaga, M.; Obora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2004, 126, 6554-6555.
20. Palladium complexes bearing the bowl-shaped phosphines were reported: (a) Matsumoto, T.; Kasai, T. Tatsumi, K. Chem. Lett. 2002, 346-347.
21. (b) Ohzu, Y.; Goto, K.; Kawashima, T. Angew. Chem., Int. Ed. 2003, 42, 5714-5717.
22. Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; Chapter 25.
23. A portion of this work was preliminarily reported: Niyomura, O.; Tokunaga, M.; Obora, Y.; Iwasawa, T.; Tsuji, Y. Angew. Chem., Int. Ed. 2003, 42, 1287-1289.
24. 3 denote tri-2-furylphosphine, tri-o-tolylphosphine, and tris(2,4,6- trimethylphenyl)phosphine, respectively.
25. Suresh, C. H.; Koga, N. Inorg. Chem. 2002, 41, 1573-1578.
26. (a) Allen, D. W.; Taylor, B. F. J. Chem. Soc., Dalton Trans. 1982, 51-54.
27. (b) Socol, S. M.; Verkade, G. J. Inorg. Chem. 1984, 23, 3487-3493.
28. (c) Keay, B. A.; Andersen, N. G. Chem. Rev. 2001, 101, 997-1030.
29. (d) Alyea, E. C.; Malito, J. Phosphorus, Sulfur, and Silicon Relat. Eiem. 1989, 46, 175-181.
30. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
31. Brevard, C.; Granger, P. Handbook of High-Resolution Multinuclear NMR; Wiley-Interscience: New York, 1981; p 158.
32. (a) Naaktgeboren, A. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1980, 102, 3350-3354.
33. (b) Elsevier, C. J.; Kowall, B.; Kragten, H. Inorg. Chem. 1995, 34, 4836-4839.
34. (c) Brown, T. H.; Green, P. J. J. Am. Chem. Soc. 1970, 92, 2359-2362.
35. (a) Yoshida, T.; Otsuka, S. Inorg. Chim. Acta 1978, 29, L257-L259.
36. (b) Waal, D. J. A. D.; Robb, W. Inorg. Chim. Acta 1978, 26, 91-96.
37. (c) Gusev, D. G.; Bakhmutov, V. I.; Grushin, V. V.; Vol'pin, M. E. Inorg. Chim. Acta 1990, 175, 19-21.
38. (d) van Gaal, H. L. M.; van den Bekerom, F. L. A. J. Organomet. Chem. 1977, 134, 237-248.
39. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: Oxford, U.K., 1997.
40. Vinod, T. K.; Hart, H. J. Org. Chem. 1991, 56, 5630-5640.
41. Ritleng, V.; Yandulov, D.; Weare, W. W.; Sehrock, R. R.; Hock, A. S. Davis, W. M. J. Am. Chem. Soc. 2004, 126, 6150-6163.
42. Tashiro, M.; Yamato, T. J. Chem. Soc., Perkin Trans. 1 1979, 176-179.
43. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
44. Cromer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. IV.
45. Ibers, J. A.; Hamilton, W. C. Acta Crystallogr. 1964, 17, 781.
46. (a) Crystal Structure Analysis Package; Rigaku and Rigaku/MSC (2000-2004), 9009 New Trails Dr., The Woodlands, TX 77381.
47. (b) Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. Chemical Crystallography Laboratory, Oxford, U. K.