Reactivity of platinum - Oxygen bonds: Kinetic and mechanistic studies of the carbonylation of platinum aryloxide complexes and the formation of (aryloxy)carbonyls

Journal of the American Chemical Society

Volumn 118, Issue 20, 1996, Pages 4846-4852

  Dockter, David W ^a,b   Fanwick, Phillip E ^a   Kubiak, Clifford P ^a  

^a PURDUE UNIVERSITY   (United States)

^b Phillips Research Center 224GB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PLATINUM COMPLEX;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029890191     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952680p     Document Type: Article

References (53)

1. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533.
2. Pearson, R. G. J. Chem. Educ. 1968, 45, 643.
3. Hartley, F. R. The Chemistry of Platinum and Palladium; Halsted Press: New York, 1973; p 169.
4. Bryndza, H. E.; Domaille, P. J.; Tam, W.; Fong, L. K.; Paciello, R. A.; Bercaw, J. E. Polyhedron 1988, 7, 1441-52.
5. Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163-88.
6. Sen, A.; Chen, J.-T.; Vetter, W. M.; Whittle, R. R. J. Am. Chem. Soc. 1987, 109, 148-156.
7. Kubota, M.; Sly, W. G.; Santarsiero, B. D.; Clifton, M. S.; Kuo, L. Organometallics 1987, 6, 1257-1259.
8. Bellon, P. L.; Manassero, M.; Porta, F.; Sansoni, M. J. Organomet. Chem. 1974, 80, 139-145.
9. Osakada, K.; Kim, Y.-J.; Yamamoto, A. J. Organomet. Chem. 1990, 382, 303.
10. Lunder, D. M.; Lobkovsky, E. B.; Streib, W. E.; Caulton, K. G. J. Am. Chem. Soc. 1991, 113, 1937-1938.
11. Kim, Y. J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096-104.
12. Bryndza, H. E.; Calabrese, J. C.; Wreford, S. S. Organometallics 1984, 3, 1603-4.
13. Bryndza, H. E.; Calabrese, J. C.; Marsi, M.; Roe, D. C.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 108, 4805-13.
14. Bryndza, H. E.; Kretchmar, S. A.; Tulip, T. H. J. Chem. Soc., Chem. Commun. 1985, 14, 977-8.
15. Milstein, D.; Calabrese, J. C.; Williams, I. D. J. Am. Chem. Soc. 1986, 108, 6387-6389.
16. Alsters, P. L.; Baesjou, P. J.; Janssen, M. D.; Kooijman, H.; Sicherer-Roetman, A.; Spek, A. L.; Koten, G. v. Organometallics 1992, 11, 4124-4135.
17. Glueck, D. S.; Winslow, L. J. N.; Bergman, R. G. Organometallics 1991, 10, 1462-79.
18. Andrews, M. A.; Gould, G. L. Organometallics 1991, 10, 387-9.
19. Lunder, D. M.; Lobkovsky, E. B.; Streib, W. E.; Caulton, K. G. J. Am. Chem. Soc. 1991, 113, 1937-1938.
20. Osakada, K.; Kim, Y.-J.; Tanaka, M.; Ishiguro, S.-i.; Ohshiro, K.; Yamamoto, A. Inorg. Chem. 1991, 30, 197-200.
21. Mandal, S. K.; Ho, D. M.; Orchin, M. Organometallics 1993, 12, 1714-1719.
22. Smith, G. D.; Hanson, B. E.; Merola, J. S.; Waller, F. J. Organometallics 1993, 12, 568-570.
23. Simpson, R. D.; Bergman, R. G. Organometallics 1993, 12, 781-96.
24. Aldridge, T. K.; Stacy, E. M.; MacMillin, D. R. Inorg. Chem. 1994, 33, 722-727.
25. Tóth, I.; Elsevier, C. J. J. Chem. Soc., Chem. Commun. 1993, 529531.
26. Woerpel, K. A.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 7884.
27. Osakada, K.; Ohshiro, K.; Yamamoto, A. Organometallics 1991, 10, 404-10.
28. Churchill, M. R.; Fettinger, J. C.; Rees, W. M.; Atwood. J. D. J. Organomet. Chem. 1986, 304, 361.
29. Hayashi, Y.; Yamamoto, T.; Yamamoto, A.; Komiya, S.; Kushi, Y. J. Am. Chem. Soc. 1986, 108, 385-391.
30. Cowan, R. L.; Trogler, W. C. J. Am. Chem. Soc. 1989, 111, 4750-61.
31. Bugno, C. D.; Pasquali, M.; Leoni, P.; Sabation. P.; Braga, D. Inorg. Chem. 1989, 28, 1390-1394.
32. Ni, J.; Kubiak, C. P. In Homogeneous Transition Metal Catalyzed Reactions; Moser. W. R., Slocum, D. W., Eds.; Advances in Chemistry Series; American Chemical Society: Washington, D C, 1992; Vol. 230, pp 515-528.
33. Rees, W. M.; Churchill, M. R.; Fettinger, J. C.; Atwood, J. D. Organometallics 1985, 4, 2179-2185.
34. Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371-81.
35. Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. Organometallics 1991, 10, 1875-87.
36. Ladipo, F. T.; Kooti, M.; Merola, J. S, Inorg. Chem. 1993, 32, 1681-1688.
37. Flood, T. C; Jensen, J. E.; Statler, J. A. J. Am. Chem. Soc 1981, 103, 4410-14.
38. Bryndza, H. E. Organometallics 1985, 4, 1686-7.
39. McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc: 1976, 98, 6521-6528.
40. Anderson, G. K.: Lumetta, G. J. Inorg Chem. 1987, 26, 1518-1524.
41. Although first prepared in 1971 by King et. al. (Inorg. Chem. 1971, 10, 1841-50). this synthesis requires less time. The yields are similar to the earlier preparation and give a product spectroscopically identical to that reported for [Pt(triphos)(Cl)][Cl].
42. 1H NMR.
43. Ambient room temperature in the NMR probe is ca. 22 °C. During the reaction the NMR tube was not removed from the probe. Due to probe design, the probe cooling air provides a thermostatic environment. Experiments with the NMR chemical shift thermometer have shown that the probe temperature would vary by less than ±1 °C over the length of the experiment. Sample heating during the actual NMR experiment, due to decoupling, should be minimal as low power WALTZ decoupling was used.
44. Fogg, P. G. T.; Gerrard, W. Solubility of Gases in Liquids, A Critical Evaluation of Gas/Liquid Systems in Theory and Practice; John Wiley and Sons: New York. 1991.
45. Karplus, M. J. Chem. Phys. 1959, 30, 11.
46. Hartley, F. R. The Chemistry of Platinum and Palladium; Halsted Press: New York, 1973; p 303.
47. McDaniel, D. H.; Brown, H. C. J. Org. Chem. 1958, 23, 420.
48. Ouellette, R. J. Can. J. Chem. 1965, 43, 707-709.
49. Bobko, E.; Tolerico, C. S. J. Org. Chem. 1983, 48, 1368-1369.
50. Ouellette, R. J.; Marks, D. L.; Miller, D. J. Am. Chem. Soc. 1967, 89, 913-917.
51. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
52. Zhong, Z.; Stang, P. J.; Arif, A. M. Orgnometallics 1990, 9, 1703-1706.
53. obs = 5.16σ + 2.20.