Transition Metal Silyl Complexes. 62.1 Platinum Dimethyl Complexes with Hemilabile P,N-Chelating Ligands: Synthesis, Structure, and Reactions with Iodotrimethylsilane and 1,2-Bis(dimethylsilyl)benzene

Organometallics

Volumn 19, Issue 1, 2000, Pages 62-71

  Pfeiffer, Jürgen ^a   Kickelbick, Guido ^a   Schubert, Ulrich ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002803901     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990665d     Document Type: Article

References (70)

1. Part 61: Pfeiffer, J.; Kickelbick, G.; Schubert, U. Organometallics, submitted for publication.
2. 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; p 241.
3. Ankersmit, H. A.; Løken, B. H.; Kooijman, H.; Spek, A. L.; Vrieze, K.; van Koten, G. Inorg. Chim. Acta 1996, 252, 141.
4. Phosphorus and halide trans.
5. de Graaf, W.; Harder, S.; Boersma, J.; van Koten, G.; Kanters, J. A. J. Organomet. Chem. 1988, 358, 545.
6. Blacker, A. J.; Clarke, M. L.; Loft, M. S.; Mahon, M. F.; Williams, J. M. J. Organometallics 1999, 18, 2867.
7. Review article on complexes with hemilabile ligands: Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27. Recently, the reversible decoordination of the nitrogen donor group incorporated in a P,N-chelating ligand was directly observed by NMR spectroscopy: Gómez-de la Torre, F.; Jalón, F. A.; López-Agenjo, A.; Manzano, B. R.; Rodríguez, A.; Sturm, T.; Weissensteiner, W.; Martínez-Ripoll, M. Organometallics 1998, 17, 4634.
8. Review article on complexes with hemilabile ligands: Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27. Recently, the reversible decoordination of the nitrogen donor group incorporated in a P,N-chelating ligand was directly observed by NMR spectroscopy: Gómez-de la Torre, F.; Jalón, F. A.; López-Agenjo, A.; Manzano, B. R.; Rodríguez, A.; Sturm, T.; Weissensteiner, W.; Martínez-Ripoll, M. Organometallics 1998, 17, 4634.
9. For recent reviews, see: (a) Tilley, T. D. In The Chemistry of Organo Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 1415. (b) Schubert, U. In Progress in Organosilicon Chemistry; Marciniec, B., Chojnowski, J., Eds.; Gordon and Breach: Switzerland, 1995; p 278. (c) Schubert, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 419. (d) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
10. For recent reviews, see: (a) Tilley, T. D. In The Chemistry of Organo Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 1415. (b) Schubert, U. In Progress in Organosilicon Chemistry; Marciniec, B., Chojnowski, J., Eds.; Gordon and Breach: Switzerland, 1995; p 278. (c) Schubert, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 419. (d) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
11. For recent reviews, see: (a) Tilley, T. D. In The Chemistry of Organo Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 1415. (b) Schubert, U. In Progress in Organosilicon Chemistry; Marciniec, B., Chojnowski, J., Eds.; Gordon and Breach: Switzerland, 1995; p 278. (c) Schubert, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 419. (d) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
12. For recent reviews, see: (a) Tilley, T. D. In The Chemistry of Organo Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 1415. (b) Schubert, U. In Progress in Organosilicon Chemistry; Marciniec, B., Chojnowski, J., Eds.; Gordon and Breach: Switzerland, 1995; p 278. (c) Schubert, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 419. (d) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
13. (a) Thorn, D. L.; Harlow, R. L. Inorg. Chem. 1990, 29, 2017.
14. (b) Tanaka, Y.; Yamashita, H.; Shimada, S.; Tanaka, M. Organometallics 1997, 16, 3246.
15. (c) Shimada, S.; Tanaka, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1856.
16. (d) Schubert, U.; Müller, C. J. Organomet. Chem. 1989, 373, 165.
17. (e) Hofmann, P.; Meier, C.; Hiller, W.; Heckel, M.; Riede, J.; Schmidt, M. U. J. Organomet. Chem. 1995, 490, 51.
18. (f) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906.
19. Pfeiffer, J.; Schubert, U. Organometallics 1999, 18, 3245.
20. Cis with respect to phosphorus and silicon.
21. (a) Drew, D.; Doyle, J. R. Inorg. Synth. 1972, 13, 48.
22. (b) Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411.
23. 2 was found to give better yields in the ligand substitution reaction than the analogous 1,5-cyclooctadiene (COD) complex. This is attributed to the smaller bite angle of nbd compared to COD, enhancing the ease of the ligand displacement: Appleton, T. G.; Hall, J. R.; Williams, M. A. J. Organomet. Chem. 1986, 303, 139, and references cited therein.
24. (a) Anderson, G. K.; Clark, H. C.; Davies, J. A. Inorg. Chem. 1981, 20, 3607.
25. (b) Anderson, G. K.; Davies, J. A.; Schoeck, D. J. Inorg. Chim. Acta 1983, 75, L251.
26. 13C NMR of Transition Metal Phosphine Complexes; Diehl, P., Fluck, E., Kosfeld, R., Eds.; NMR, Basic Principles and Progress, Vol. 16; Springer: Berlin and Heidelberg, 1979.
27. (a) Kuyper, J. Inorg. Chem. 1977, 16, 2171.
28. (b) Kuyper, J. Inorg. Chem. 1978, 17, 4634.
29. (c) Levy, C. J.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1995, 2115.
30. (d) Levy, C. J.; Vittal, J. J.; Puddephatt, R. J. Organometallics 1996, 15, 35.
31. (e) Levy, C. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1997, 119, 10127.
32. (f) Vittal, J. J.; Puddephatt, R. J. Organometallics 1996, 15, 2108.
33. Addition of Si-halogen bonds to Pt(0) complexes, e.g.: Yamashita, H.; Tanaka, M.; Goto, M. Organometalllics 1997, 16, 4696.
34. Levy, C. J.; Puddephatt, R. J. Organometallics 1995, 14, 5019.
35. Levy, C. J.; Vittal, J. J.; Puddephatt, R. J. Organometallics 1994, 13, 1559.
36. (a) Grim, S.; Keiter, R. L. Inorg. Chem. 1967, 6, 1133.
37. (b) Heaton, B. T.; Pidcock, A. J. Organomet. Chem. 1968, 14, 235.
38. (c) Clark, H. C.; McBride, S. S.; Payne, N. C.; Wong, C. S. J. Organomet. Chem. 1979, 178, 393.
39. (d) Osakada, K.; Kim, Y.-J.; Yamamoto, A. J. Organomet. Chem. 1990, 382, 303.
40. (e) Bryndza, H. E.; Calabrese, J. C.; Marsi, M.; Roe, D. C.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 108, 4805.
41. (f) Andrews, M. A.; Gould, G. L. Organometallics 1991, 10, 387.
42. (g) Schmidbaur, H.; Adlkofer, J. Chem. Ber. 1974, 107, 3680.
43. (a) Shimada, S.; Rao, M. L. N.; Tanaka, M. Organometallics 1999, 18, 291.
44. (b) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289.
45. (c) Eaborn, C.; Mutham, T. N.; Pidcock, A. J. Organomet. Chem. 1973, 63, 107.
46. (d) Tanaka, M.; Uchimura, Y. Bull. Chim. Soc. Fr. 1992, 129, 667.
47. Kapteijn, G. M.; Spec, M. R. P.; Grove, D. M.; Kooijman, H.; Spek. A. L.; van Koten, G. Organometallics 1996, 15, 1405.
48. Rauchfuss, T. B.; Patino, F. T.; Roundhill, D. M. Inorg. Chem. 1975, 14, 652.
49. Braun, S.; Kalinowski, H.-O.; Berger, S. 150 and More Basic NMR Experiments; Wiley-VCH: Weinheim, 1998; p 136.
50. 2), 7.10-7.80 (m, 10 H, Ar-H).
51. Thorn, D. L.; Calabrese, J. C. J. Organomet. Chem. 1988, 342, 269.
52. Assmann, B.; Angermann, K.; Paul, M.; Riede, J.; Schmidbaur, H. Chem. Ber. 1995, 125, 891.
53. Ling, E. C. H.; Allen, G. W.; Hambley, T. W. J. Chem. Soc., Dalton Trans. 1993, 3705. In some cases, longer Pt-N bond lengths have been observed in pentacoordinated platinum(II) compounds, e.g.: (a) Wernberg, O.; Hazell, A. J. Chem. Soc., Dalton Trans. 1980, 973. (b) De Renzi, A.; Di Blasio, B.; Saporito, A.; Scalone, M.; Vitagliano, A. Inorg. Chem. 1980, 19, 960.
54. Ling, E. C. H.; Allen, G. W.; Hambley, T. W. J. Chem. Soc., Dalton Trans. 1993, 3705. In some cases, longer Pt-N bond lengths have been observed in pentacoordinated platinum(II) compounds, e.g.: (a) Wernberg, O.; Hazell, A. J. Chem. Soc., Dalton Trans. 1980, 973. (b) De Renzi, A.; Di Blasio, B.; Saporito, A.; Scalone, M.; Vitagliano, A. Inorg. Chem. 1980, 19, 960.
55. Ling, E. C. H.; Allen, G. W.; Hambley, T. W. J. Chem. Soc., Dalton Trans. 1993, 3705. In some cases, longer Pt-N bond lengths have been observed in pentacoordinated platinum(II) compounds, e.g.: (a) Wernberg, O.; Hazell, A. J. Chem. Soc., Dalton Trans. 1980, 973. (b) De Renzi, A.; Di Blasio, B.; Saporito, A.; Scalone, M.; Vitagliano, A. Inorg. Chem. 1980, 19, 960.
56. (a) Mitchell, G. P.; Tilley, T. D. Angew. Chem., Int. Ed. Engl. 1998, 39, 2524.
57. (b) McIndoe, J. S.; Nicholson, B. K. J. Organomet. Chem. 1999, 577, 181.
58. See, e.g.: (a) Lin, I. J. B.; Kao, L. T. C.; Wu, F. J.; Lee, G. H.; Wang, Y. J. Organomet. Chem. 1986, 309, 225. (b) Engelter, C.; Moss, J. R.; Nissimbeni, L. R.; Niven, M. L.; Reid, G.; Spiers, J. C. J. Organomet. Chem. 1986, 375, 255. (c) Argazzi, R.; Bergamini, P.; Costa, E.; Gee, V.; Hogg, J. K.; Martin, A.; Orpen, A. G.; Pringle, P. G. Organometallics 1996, 15, 5591.
59. See, e.g.: (a) Lin, I. J. B.; Kao, L. T. C.; Wu, F. J.; Lee, G. H.; Wang, Y. J. Organomet. Chem. 1986, 309, 225. (b) Engelter, C.; Moss, J. R.; Nissimbeni, L. R.; Niven, M. L.; Reid, G.; Spiers, J. C. J. Organomet. Chem. 1986, 375, 255. (c) Argazzi, R.; Bergamini, P.; Costa, E.; Gee, V.; Hogg, J. K.; Martin, A.; Orpen, A. G.; Pringle, P. G. Organometallics 1996, 15, 5591.
60. See, e.g.: (a) Lin, I. J. B.; Kao, L. T. C.; Wu, F. J.; Lee, G. H.; Wang, Y. J. Organomet. Chem. 1986, 309, 225. (b) Engelter, C.; Moss, J. R.; Nissimbeni, L. R.; Niven, M. L.; Reid, G.; Spiers, J. C. J. Organomet. Chem. 1986, 375, 255. (c) Argazzi, R.; Bergamini, P.; Costa, E.; Gee, V.; Hogg, J. K.; Martin, A.; Orpen, A. G.; Pringle, P. G. Organometallics 1996, 15, 5591.
61. One referee has suggested an alternative explanation for the enhanced reactivity of the P,N-chelated complexes compared to the bis(phosphine) complexes on the basis of the electronic ground-state properties. However, recent results indicate that reactions of late transition metal diphosphine complexes often occur via predissociation of a phosphine ligand rather than by an associative mechanism: (a) Ozawa, F.; Hikida, T. Organometallics 1996, 15, 4501. (b) Romeo, R.; Alibrandi, G. Inorg. Chem. 1997, 36, 4822. In addition, the difference in the reactivity of complex 2 compared to 1, 3, and 4 can hardly be explained based solely on electronic effects.
62. One referee has suggested an alternative explanation for the enhanced reactivity of the P,N-chelated complexes compared to the bis(phosphine) complexes on the basis of the electronic ground-state properties. However, recent results indicate that reactions of late transition metal diphosphine complexes often occur via predissociation of a phosphine ligand rather than by an associative mechanism: (a) Ozawa, F.; Hikida, T. Organometallics 1996, 15, 4501. (b) Romeo, R.; Alibrandi, G. Inorg. Chem. 1997, 36, 4822. In addition, the difference in the reactivity of complex 2 compared to 1, 3, and 4 can hardly be explained based solely on electronic effects.
63. Willker, W.; Leibfritz, D.; Kerssebaum, R.; Bernel, W. Magn. Reson. Chem. 1993, 31, 287.
64. Hurd, R. E. J. Magn. Reson. 1990, 87, 422.
65. Malet, R.; Morena-Mañas, M.; Parella, T.; Pleixats, R. J. Org. Chem. 1996, 61, 758.
66. q: quarternary aromatic carbon atom.
67. (a) Gilman, H.; Banner, I. J. Am. Chem. Soc. 1940, 62, 344.
68. (b) Fritz, H. P.; Gordon, I. R.; Schwarzhans, K. E.; Venzani, L. M. J. Chem Soc. (A) 1965, 5210.
69. (a) Bohme, H.; Hartke, K. Chem. Ber. 1960, 93, 1305.
70. (b) Aguiar, A. M.; Hansen, K. C.; Mague, J. T. J. Chem. Soc. (A) 1967, 2883.