Electrophilic methylplatinum complexes: A theoretical study of the mechanism of C-C and C-H bond formation and activation

Organometallics

Volumn 17, Issue 8, 1998, Pages 1478-1486

  Hill, Geoffrey S ^a   Puddephatt, Richard J ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000660110     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9709291     Document Type: Article

References (34)

1. (a) Shilov A. E. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Riedel: Dordrecht, The Netherlands, 1984.
2. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
3. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
4. (a) Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848.
5. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961.
6. (a) Hutson, A. C.; Lin, M.; Basickes, N.; Sen, A. J. Organomet. Chem. 1995, 504, 69.
7. (a) Low, J. J.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115.
8. (b) Low, J. J.; Goddard, W. A. Organometallics 1986, 5, 609.
9. (a) Hill, G. S.; Vittal, J. J.; Puddephatt, R. J. Organometallics 1997, 16, 1209.
10. (b) Hill, G. S.; Puddephatt, R. J. J. Am. Chem. Soc. 1996, 118, 8745.
11. (c) Hill, G. S.; Rendina, L. M.; Puddephatt, R. J. Organometallics 1995, 14, 4966.
12. (d) Jenkins, H. A.; Yap, G. F. A.; Puddephatt, R. J. Organometallics 1997, 16, 1946.
13. (a) O'Reilly, S. A.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1996, 118, 8, 5684.
14. (b) Canty, A. J.; Dedieu, A.; Jin, H.; Milet, A.; Richmond, M. K. Organometallics 1996, 15, 2845.
15. (c) De Felice, V.; De Renzi, A.; Panunzi, A.; Tesauro, D. J. Organomet. Chem. 1995, 488, C13.
16. (a) Goldberg, K. I.; Yan, J.; Breitung, E. M. J. Am. Chem. Soc. 1995, 117, 6889.
17. (b) Goldberg, K. I.; Yan, J.; Winter, E. L. J. Am. Chem. Soc. 1994, 116, 1573.
18. (a) Brown, M. P.; Puddephatt, R. J.; Upton, C. E. E. J. Chem. Soc., Dalton Trans. 1974, 2457.
19. (b) Brown, M. P.; Puddephatt, R. J.; Upton, C. E. E. J. Organomet. Chem. 1973, 49, C61.
20. (c) Roy, S.; Puddephatt, R. J.; Scott, J. D. J. Chem. Soc., Dalton Trans. 1989, 2121.
21. Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241.
22. (a) Lashanizadehgan, M.; Rashidi, M.; Hux, J. E.; Puddephatt, R. J.; Ling, S. S. M. J. Organomet. Chem. 1984, 269, 317.
23. (b) Goldberg, K. I. personal communication.
24. (c) Hill, G. S.; Puddephatt, R. J. Organometallics 1997, 16, 4522.
25. 3(bipy)] gives mostly methane rather than ethane.
26. Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255.
27. (a) Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1997, 16, 1355 and references therein,
28. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
29. (c) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
30. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
31. 8 complexes, which have features in common with reductive eliminations. Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y., Chen W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.1; Gaussian, Inc.: Pittsburgh, PA, 1995.
33. 3 to illustrate the relative energies in the two cases. In terms of absolute energies, it could be argued that a phosphine stabilizes platinum(II) or destabilizes platinum(IV) with respect to an amine ligand.
34. Mealli, C.; Proserpio, D. M. J. Chem. Educ. 1990, 67, 399.