Kinetic studies on the reductive elimination of cis-PtMe(SiPh3)(PMe2Ph)2 and cis-PtMe(GePh3)(PMe2Ph)2. The first comparison between C-Si and C-Ge reductive elimination

Organometallics

Volumn 17, Issue 6, 1998, Pages 1018-1024

  Ozawa, Fumiyuki ^a   Hikida, Toshihiko ^a   Hasebe, Koh ^a   Mori, Takuya ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000108694     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970841n     Document Type: Review

References (46)

1. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; Wiley-Interscience: New York, 1992.
2. (a) Brown, J. M.; Cooley, N. A. Chem. Rev. (Washington, D.C.) 1988, 88, 1031.
3. (b) Yamamoto, A. Organotransition Metal Chemistry, Fundamental Concepts and Applications; Wiley-Interscience: New York, 1986.
4. (c) 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.
5. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
6. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
7. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
8. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
9. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
10. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
11. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
12. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
13. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
14. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
15. For recent examples of reductive elimination giving a carbon-heteroatom bond other than the carbon-silicon bond, see: (a) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. (e) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135. (f) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669. (g) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724. (h) Han, L.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (i) Nakazawa, H.; Matsuoka, Y.; Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385. (j) Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (k) Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906.
16. Ozawa, F.; Hikida, T.; Hayashi, T. J. Am. Chem. Soc. 1994, 116, 2844.
17. (a) Tanaka, Y.; Yamashita, H.; Shimada, S.; Tanaka, M. Organometallics 1997, 16, 3246.
18. (b) Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 6456.
19. (c) Akita, M.; Hua, R.; Oku, T.; Tanaka, M.; Moro-oka, Y. Organometallics 1996, 15, 4162.
20. (d) Okazaki, M.; Tobita, H.; Ogino, H. Organometallics 1996, 15, 2790.
21. (e) Mitchell, G. P.; Tilley, T. D. Organometallics 1996, 15, 3477.
22. (f) Schubert, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 419.
23. (g) Lin, W.; Wilson, S. R.; Girolami, G. S. Organometallics 1994, 13, 2309.
24. (h) Schubert, U.; Müller, C. J. Organomet. Chem. 1989, 373, 165.
25. (i) Brinkman, K. C.; Blakeney, A. J.; Krone-Schmidt, W.; Gladysz, J. A. Organometallics 1984, 3, 1325.
26. (a) Brunstein, P.; Knorr, M. J. Organomet. Chem. 1995, 500, 21.
27. (b) Recatto, C. A. Aldrichimica Acta 1995, 28, 85.
28. (c) Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; p 1415.
29. Low, J. J.; Goddard, W. A., III. J. Am. Chem. Soc. 1986, 108, 6115 and references therein.
30. (a) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1991, 113, 5063.
31. (b) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373.
32. (c) Levy, C. J.; Puddephatt, R. J. Organometallics 1995, 14, 5019.
33. (d) Pilcher, G.; Skinner, H. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, U.K., 1982; Vol. 1, p 43.
34. Ozawa, F.; Hikida, T. Organometallics 1996, 15, 4501.
35. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335. Bresciani-Pahor, N.; Forcolin, M.; Marzilli, L. G.; Randaccio, L.; Summers, M. F.; Toscano, P. J. Coord. Chem. Rev. 1985, 63, 1.
36. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335. Bresciani-Pahor, N.; Forcolin, M.; Marzilli, L. G.; Randaccio, L.; Summers, M. F.; Toscano, P. J. Coord. Chem. Rev. 1985, 63, 1.
37. P-P = 22 Hz).
38. 8d
39. Burnham, R. A.; Stobert, S. R. J. Chem. Soc., Dalton Trans. 1977, 1489. Cardin, D. J.; Lappert, M. F.; Litzow, M. R.; Spalding, T. R. J. Chem. Soc. A 1971, 2262. Spalding, T. R. J. Organomet. Chem. 1978, 149, 371. Novak, I.; Huang, W.; Luo, L.; Huang, H. H.; Ang, H. G.; Zybill, C. E. Organometallics 1997, 16, 1567.
40. Burnham, R. A.; Stobert, S. R. J. Chem. Soc., Dalton Trans. 1977, 1489. Cardin, D. J.; Lappert, M. F.; Litzow, M. R.; Spalding, T. R. J. Chem. Soc. A 1971, 2262. Spalding, T. R. J. Organomet. Chem. 1978, 149, 371. Novak, I.; Huang, W.; Luo, L.; Huang, H. H.; Ang, H. G.; Zybill, C. E. Organometallics 1997, 16, 1567.
41. Burnham, R. A.; Stobert, S. R. J. Chem. Soc., Dalton Trans. 1977, 1489. Cardin, D. J.; Lappert, M. F.; Litzow, M. R.; Spalding, T. R. J. Chem. Soc. A 1971, 2262. Spalding, T. R. J. Organomet. Chem. 1978, 149, 371. Novak, I.; Huang, W.; Luo, L.; Huang, H. H.; Ang, H. G.; Zybill, C. E. Organometallics 1997, 16, 1567.
42. Burnham, R. A.; Stobert, S. R. J. Chem. Soc., Dalton Trans. 1977, 1489. Cardin, D. J.; Lappert, M. F.; Litzow, M. R.; Spalding, T. R. J. Chem. Soc. A 1971, 2262. Spalding, T. R. J. Organomet. Chem. 1978, 149, 371. Novak, I.; Huang, W.; Luo, L.; Huang, H. H.; Ang, H. G.; Zybill, C. E. Organometallics 1997, 16, 1567.
43. Clemmit, A. F.; Glockling, F. J. Chem. Soc. A 1971, 1164.
44. IV-E bond energies was established on the basis of thermochemical experiments: E = Si > Ge > Sn. Levy, C. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1997, 119, 10127; Organometallics 1997, 16, 4115. If this order is applied to the present Pt(II) systems, one must consider that the higher reactivity of 1b compared to that of 2b is mainly due to the stronger C-Si bond rather than C-Ge bond. The transition states may strongly resemble the reductive-elimination products.
45. IV-E bond energies was established on the basis of thermochemical experiments: E = Si > Ge > Sn. Levy, C. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1997, 119, 10127; Organometallics 1997, 16, 4115. If this order is applied to the present Pt(II) systems, one must consider that the higher reactivity of 1b compared to that of 2b is mainly due to the stronger C-Si bond rather than C-Ge bond. The transition states may strongly resemble the reductive-elimination products.
46. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. IV.