Mechanistic studies of catalytic olefin dimerization reactions using electrophilic η3-allyl-palladium(II) complexes

Journal of the American Chemical Society

Volumn 118, Issue 26, 1996, Pages 6225-6234

  DiRenzo, Geraldine M ^a   White, Peter S ^a   Brookhart, Maurice ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROPHOTOMETRY; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030018694     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9602354     Document Type: Article

References (58)

1. Parshall, G. W.; Ittel, S. D. In Homogeneous Catalysis, 2nd ed.; Wiley-Interscience: New York, 1992; p 242.
2. Weissermel, K.; Arpe, H. J. In 2nd ed.; Verlag Chemie: Weinheim, Germany, 1993.
3. Alderson, T. U.S. Patent 3 013 066, 1961.
4. Alderson, T.; Jenner, E.; Lindsey, R. V. J. Am. Chem. Soc. 1965. 87, 5638.
5. Nugent, W. A.; McKinney, R. J. Mol. Catal. 1985, 29, 65.
6. Singleton, D. M. U. S. Patent 4 638 084, 1987.
7. Kovalev, I. P.; Kolmogorov, Y. N.; Strelenko, Y. A.; Ignatenko, A. V.; Vinogradov, M. G.; Nikishin, G. I. J. Organomet. Chem. 1991, 420, 125.
8. Nikishin, G. I.; Kovalev, I. P.; Klimova, T. E.; Ignatenko, A. V. Tetrahedron Lett. 1991, 32, 1077.
9. Brookhart, M.; Sabo-Etienne, S. J. Am. Chem. Soc. 1991, 113, 2777.
10. Brookhart, M. S.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394.
11. Brookhart, M.; Hauptman, E. J. Am. Chem. Soc. 1992, 114, 4437.
12. Hauptman, E.; Sabo-Etienne, S.; White, P. S.; Brookhart, M.; Garner, M. J.; Fagan, P. J.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 8038.
13. McKinney, R. J. U. S. Patent 4 485 256, 1986.
14. McKinney, R. J.; Colton, M. C. Organometallics 1986, 5, 1080.
15. Ren, C. Y.; Cheng, W. C.; Chan, W. C.; Yeung, C. H.; Lau, C. P. J. Mol. Catal. 1990,59, L1.
16. Sustmann, R.; Hornung, H. J.; Schupp, T.; Patzke, B. J. Mol. Catal. 1993, 85, 149.
17. Barlow, M. G.; Bryant, M, J.; Haszeldine, R. N.; Mackie, A. G. J. Organomet. Chem. 1970, 21, 215.
18. Oehme, G.; Pracejus, H. J. Organomet. Chem. 1987, 320, C56.
19. Nugent, W. A.; Hobbs, F. W. J. Org. Chem. 1983, 48, 5364.
20. Nugent, W. A. U. S. Patent 4 451 665, 1984.
21. Tkatchenko, I.; Neibecker, D.; Grenouillet, P. French Patent 2 524 341, 1983.
22. Tkatchenko, I.; Neibecker, D.; Grenouillet, P. Organometallics 1984, 3, 1130.
23. Oehme, G.; Grassert, I.; Mennenga, H.; Baudisch, H. J. Mol. Catal. 1986, 37, 53.
24. Grenouillet, P.; Neibecker, D.; Tkatchenko, I. French Patent 2 596 390, 1987.
25. Guibert, I.; Neibecker, D.; Tkatchenko, I. J. Chem. Soc., Chem. Commun. 1989, 1850.
26. Perron, R.; Mutez, S. European Patent 305 302, 1989.
27. Wilke, G.; Sperling, K.; Stehling, L. U. S. Patent 4 594 447, 1986.
28. Wilke, G. Angew. Chem. Int. Ed. Engl. 1988, 27, 185.
29. Pertici, P.; Ballantini. V.; Salvadori, P.; Bennett, M. A. Organometallics 1995, 14, 2565.
30. Grenouillet, P.; Neibecker, D.; Tkatchenko, I. Organometallics 1984, 3, 1130.
31. Grenouillet, P.; Neibecker, D.; Tkatchenko, I. U.S. Patent 4 889 949, 1989.
32. Tatsuno, Y.; Yoshida, T. In Inorganic Synthesis; Shriver, D. F., Ed.; John Wiley & Sons: New York, 1979; p 220.
33. Powell, J.; Shaw, B. L. Inorg. Phys. Theor. 1967, 1839.
34. Hayashi, Y.; Matsumoto, K.; Nakamura, Y. J. Chem. Soc., Dalton Trans. 1989, 1519.
35. Brookhart, M.; Grant, B.; Volpe, A. F. Organometallics 1992, 11, 3920.
36. Musco, A.; Pontellini, R.; Grassi, M.; Sironi, A.; Meille. S. V.; Ruegger, H.; Ammann, C.; Pregosin, P. S. Organometallics 1988, 7, 2130.
37. Powell, J.; Robinson, S. D.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1965, 78.
38. Ramey. K. C.; Statton, G. L, J. Am. Chem. Soc. 1966, 88, 4387.
39. Lukas, J.; Coren, S.; Blom. J. E. J. Chem. Soc., Chem. Commun. 1969, 1303.
40. Lippard, S. J.; Morehouse, S. M. J. Am. Chem. Soc. 1972, 94, 6949.
41. van Leeuwen, P. W. N. M.; Praat, A. P. J. Chem. Soc., Chem. Commun. 1970, 365.
42. Cesarotti, E.; Grassi, M.; Prati, L.; Demartin, F. J. Organomet. Chem. 1989, 370, 407.
43. 31P sites. This is consistent with the allyl rocking proposal (9 ⇀ 9′). If two conformations of the tricyclohexylphosphine ligand were possible, then three isomers would be expected for 9. Only one isomer of the three would exhibit inequivalent phosphorus nuclei. It seems unlikely that this would be the sole isomer detectable. Thus we favor allyl rocking to account for the dynamics of 9 and, by analogy, for the dynamics of the other allyl complexes.
44. Sandstrom, J. Dynamic NMR Spectroscopy; Academic Press: New York, 1982.
45. Allerhand, A.; Gutowsky, H. S.; Jonas, J.; Meinzer, R. A. J. Am. Chem. Soc. 1966, 88, 3185.
46. Gordon, J. G.; Holm, R. H. J. Am. Chem. Soc. 1970, 92, 5319.
47. Eaton, S. S.; Hutchinson, J. R.; Holm, R. H.; Muetterties. E. L. J. Am. Chem. Soc. 1972, 94, 6411.
48. Very recently, the reaction of similar allyl-palladium complexes with ethylene was directly observed: Mecking, S.; Keim, W. Organometallics In press.
49. Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137.
50. There is no evidence that this species is a bis-ethy!ene complex. However, since ethylene readily displaces diethyl ether in these cationic species, we believe a bis-ethylene complex is more likely than a solvated mono-ethylene complex.
51. Sheffy, F. K.; Godschalx, J. P.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4833.
52. Brookhart, M.; Rix, F. C.; DeSimone, J. M. J. Am. Chem. Soc. 1992, 114, 5894.
53. We cannot rule out the presence of both 16 and 16′ in rapid equilibrium at 25 °C. Associative exchange of bound and free acrylate is rapid on the NMR time scale at 25 °C (see above); the five coordinate intermediate responsible for associative exchange thus could provide a mechanism for very rapid interconversion of 16 and 16′.
54. The NMR analysis of the sequence 19 → 20 → 21 is more complicated than the analogous transformations for the tricyclohexyl phosphine complexes 13 → 14 → 16. The rate of 19 → 20 is only slightly faster than the 20 → 21 conversion and thus 20 never appears without substantial amounts of either 19 and/or 21 present.
55. Johnson, L. K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc. 1996. 118, 267.
56. Hauptman, E.; Brookhart, M.; Calabrese, J. C.; Fagan, P. J. Organometallics 1994, 13, 774.
57. Grant, B.; Brookhart, M. Unpublished results.
58. Gabe, E. J.; Le Page, Y. L.; Charland, J. P.; Lee, F. L.; White, P. S. J. Appl. Crystallogr. 1989, 22, 384.