Rhodium(I) and iridium(I) complexes with β-keto phosphine or phosphino enolate ligands. Catalytic transfer dehydrogenation of cyclooctane

Organometallics

Volumn 15, Issue 26, 1996, Pages 5551-5567

  Braunstein, Pierre ^a   Chauvin, Yves ^b   Nähring, Jens ^a,b   DeCian, André ^a   Fischer, Jean ^a   Tiripicchio, Antonio ^c   Ugozzoli, Franco ^c  

^a CNRS   (France)

^b IFP ENERGIES NOUVELLES   (France)

^c UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001367711     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960814h     Document Type: Article

References (82)

1. (a) Braunstein, P.; Chauvin, Y.; Nähring, J.; DeCian, A.; Fischer, J. J. Chem. Soc., Dalton Trans. 1995, 863.
2. (b) Braunstein, P.; Chauvin, Y.; Nähring, J.; Dusausoy, Y.; Tiripicchio, A.; Ugozzoli, F. J. Chem. Soc., Dalton Trans. 1995, 851.
3. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; Wiley: New York, 1992.
4. Spencer, A. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J., Eds.; Pergamon Press: Oxford, England, 1987; Vol. 6, p. 229.
5. Halpern, J. Inorg. Chim. Acta 1981, 50, 11.
6. Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27.
7. Bouaoud, S.-E.; Braunstein, P.; Grandjean, D.; Matt, D.; Nobel, D. Inorg. Chem. 1986, 25, 3765.
8. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247.
9. (a) Keim, W. Chem.-Ing.-Techn. 1984, 56, 850.
10. (b) Klabunde, U.; Tulip, T. H.; Roe, D. C.; Ittel, S. D. J. Organomet. Chem. 1987, 334, 141.
11. (c) Keim, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 235.
12. (d) Mercier, S. Ph.D. Thesis, Université Paris VI, 1993.
13. (d) Keim, W. New J. Chem. 1994, 18, 93.
14. (e) Braunstein, P.; Chauvin, Y.; Mercier, S.; Saussine, L.; DeCian, A.; Fischer, J. J. Chem. Soc., Chem. Commun. 1994, 2203.
15. (a) Maguire, J. A.; Goldman, A. S. J. Am. Chem. Soc. 1991, 113, 6706.
16. (b) Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492.
17. (c) Shih, K.-C.; Goldman, A. S. Organometallics 1993, 12, 3390.
18. (d) Miller, J. A.; Knox, L. K. J. Chem. Soc., Chem. Commun. 1994, 1449.
19. (a) Novikowa, Z. S.; Proskurnina, M. V.; Petrovskaya, L. I.; Bogdanova, I. V.; Galitskova, N. P.; Lutsenko, I. F. J. Gen. Chem. USSR (Engl. Transl.) 1967, 37, 1972.
20. (b) Novikowa, Z. S.; Galitskova, N. P.; Kozlov, V. A.; Lutsenko, I. F. J. Gen. Chem. USSR (Engl. Transl.) 1971, 41, 838.
21. Moulton, C. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 299.
22. (a) Brunner, H.; Dylla, M. E.; Hecht, G. A. M.; Pieronczyk, W. Z. Naturforsch. 1982, 37B, 404.
23. (b) Dylla, M. E. Zulassungsarbeit, Universität Regensburg, 1980.
24. Braunstein, P.; Matt, D.; Mathey, F.; Thavard, D. J. Chem. Res., Miniprint 1978, 3041; J. Chem. Res., Synop. 1978, 232.
25. Braunstein, P.; Matt, D.; Mathey, F.; Thavard, D. J. Chem. Res., Miniprint 1978, 3041; J. Chem. Res., Synop. 1978, 232.
26. Eibach, F. Diplomarbeit, Universität Marburg, 1976.
27. Knight, D. A.; Cole-Hamilton, D. J.; Cupertino, D. C. J. Chem. Soc., Dalton Trans. 1990, 3051.
28. Streitweiser, A.; Heathcock, C. H. In Einführung in die organische Chemie; Macmillan: New York, 1980; p 483.
29. Demerseman, B.; Guilbert, B.; Renouard, C.; Gonzalez, M.; Dixneuf, P. H. Organometallics 1993, 12, 3906.
30. Günther, H NMR Spectroskopie, 3rd ed.; Thieme Verlag-Stuttgart, Germany, 1992; p 310.
31. Cramer, R.; Kline, J. B.; Roberts, J. D. J. Am. Chem. Soc. 1969, 2519.
32. Braunstein, P.; Matt, D.; Nobel, D.; Balegroune, F.; Bouaoud, S.-E.; Grandjean, D.; Fischer, J. J. Chem. Soc., Dalton Trans. 1988, 27, 353.
33. Andrieu, J.; Braunstein, P.; Naud, F. J. Chem. Soc., Dalton Trans. 1996, 2903.
34. (a) Lindner, E.; Wang, Q.; Mayer, H. A.; Bader, A.; Kühbauch, H.; Wegner, P. Organometallics 1993, 12, 3291.
35. (b) Lindner, E.; Wang, Q.; Mayer, H. A.; Bader, A. J. Organomet. Chem. 1993, 458, 229.
36. (c) Werner, H.; Hampp, A.; Peters, K.; Peters, E. M.; Walz, L.; von Schnering, H. G. Z. Naturforsch. 1990, 45B, 1548.
37. (d) Werner, H.; Hampp, A.; Windmüller, B. J. Organomet. Chem. 1992, 435, 169.
38. Lindner, E.; Wang, Q.; Mayer, H. A.; Fawzi, R.; Steinmann, M. Organometallics 1993, 12, 1865.
39. Allgeier, A. M.; Singewald, E. T.; Mirkin, C. A.; Stern, C. L. Organometallics 1994, 13, 2928.
40. Lindner, E.; Wang, Q.; Mayer, H. A.; Fawzi, R.; Steinmann, M. J. Organomet. Chem. 1993, 453, 289.
41. Sen, A.; Lai, T.-W. Organometallics 1983, 2, 1059.
42. Bouaoud, S.-E.; Braunstein, P.; Grandjean, D.; Matt, D.; Nobel, D. Inorg. Chem. 1988, 27, 2279.
43. Balegroune, F.; Braunstein, P.; Grandjean, D.; Matt, D.; Nobel, D. Inorg. Chem. 1988, 27, 3320.
44. Braunstein, P.; Nobel, D. Chem. Rev. 1989, 89, 1927.
45. Balegroune, F.; Braunstein, P.; Gomes Carneiro, T. M.; Grandjean, D.; Matt, D. J. Organomet. Chem. 1989, 367, 117.
46. Braunstein, P.; Kelly, D. G.; Dusausoy, Y.; Tiripicchio, A. Inorg. Chem. 1993, 32, 4835.
47. Esteruelas, M. A.; López, A. M.; Oro, L. A.; Pérez, A.; Schulz, M.; Werner, H. Organometallics 1993, 12, 1823.
48. Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1976, 98, 2134.
49. James, B. R. Homogeneous Hydrogenation; Wiley: New York, 1973.
50. (a) Crabtree, R. H. In The Chemistry of Alkanes and Cycloalkanes; Patai, S., Ed.; Wiley: New York, 1992; p 653.
51. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
52. Crabtree, R. H.; Mellea, M. F.; Mihelcic, J. M.; Quirk, J. M. J. Am. Chem. Soc. 1982, 104, 107.
53. (a) Nomura, K.; Saito, Y. J. Chem. Soc., Chem. Commun. 1988, 161.
54. (b) Sakakura, T.; Sodeyama, T.; Tokunaga, M.; Tanaka, M. Chem. Lett. 1988, 263.
55. (c) Maguire, J. A.; Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1989, 111, 7088.
56. (d) Maguire, J. A.; Boese, W. T.; Goldman, M. E.; Goldman, A. S. Coord. Chem. Rev. 1990, 97, 179.
57. Wang, K.; Rosini, G. P.; Nolan, S. P.; Goldman, A. S. J. Am. Chem. Soc. 1995, 117, 5082.
58. Another possibility would be that dissociation of the triarylphosphine may precede the approach of the alkane.
59. Chency, A. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1972, 754, 860.
60. Garrou, P. Chem. Rev. 1985, 85, 171.
61. Burk, M. J.; Crabtree, R. H. J. Am. Chem. Soc. 1987, 109, 8025.
62. 2] the rate decreased with an increasing ratio of solution to gas phase volume.
63. Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855.
64. Sheridan, P. S. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, England, 1987; Vol. 4, p 901.
65. This is in contrast to the previously observed catalytic isomerization of hexene with 7 in toluene (see above). The lower polarity of the cyclooctane/norbornane solvent compared to that of toluene may suppress the formation of monohydride species.
66. 2] compared to 7 or to a change in the olefin acceptor.
67. Albers, M. O.; Coville, N. J. Coord. Chem. Rev. 1984, 53, 227.
68. Sakakura, T.; Sodeyama, T.; Tanaka, M. New. J. Chem. 1989, 13, 737.
69. Crabtree, R. H.; Demou, P. C.; Eden, D.; Mihelcic, J. M.; Parnell, C. A.; Quirk, J. M.; Morris, G. E. J. Am. Chem. Soc. 1982, 104, 6994.
70. (a) Belli, J.; Jensen, C. M. Organometallics 1996, 15, 1532.
71. (b) Braunstein, P.; Chauvin, Y.; Nähring, J. Unpublished results.
72. Burfield, D. R.; Smithers, R. H. J. Org. Chem. 1978, 43, 3966.
73. Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G. J. Chem. Soc. A 1966, 1711.
74. Stephenson, T. A.; Wilkinson, G. J. Inorg. Nucl. Chem. 1966, 28, 945.
75. Abel, E. W.; Bennett, M. A.; Wilkinson, G. J. Chem. Soc. 1959, 3178.
76. Hoffmann, P.; Meier, C.; Englert, U.; Schmidt, M. U. Chem. Ber. 1992, 125, 353.
77. Cramer, R. Inorg. Chem. 1962, 1, 722.
78. van der Ent, A.; Onderdelinden, A. L. Inorg. Synth. 1990, 28, 90.
79. Molen, An Interactive Structure Determination Procedure; Enraf-Nonius, Delft, The Netherlands, 1990.
80. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV.
81. Sheldrick, G. M. SHELX-76, Program for Crystal Structure Determination' University of Cambridge, Cambridge, England, 1976. SHELX-86, Program for the Solution of Crystal Structures; University of Göttingen, Göttingen, Germany, 1986.
82. Sheldrick, G. M. SHELX-76, Program for Crystal Structure Determination' University of Cambridge, Cambridge, England, 1976. SHELX-86, Program for the Solution of Crystal Structures; University of Göttingen, Göttingen, Germany, 1986.