Synthesis and structure of an unusual zirconium hydride amide complex. Mechanistic studies of the reactions of transition-metal amides with silanes

Journal of the American Chemical Society

Volumn 121, Issue 22, 1999, Pages 5350-5351

  Liu, Xiaozhan ^a   Wu, Zhongzhi ^a   Peng, Zhihui ^b   Wu, Yun Dong ^b   Xue, Ziling ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; HYDRIDE DERIVATIVE; SILANE; UNCLASSIFIED DRUG; ZIRCONIUM;

ARTICLE; CALCULATION; CHEMICAL REACTION; LIGAND BINDING; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033538278     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984324n     Document Type: Article

References (60)

1. (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Harwood: Chichester, U.K., 1980.
2. (b) Chisholm, M. H.; Rothwell, I. P. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: New York, 1987; Vol. 2.
3. 2 (M = Ti, R = Me; M = Zr, R = Et). Creemers, H. M. J. C.; Verbeek, F.; Noltes, J. G. J. Organomet. Chem. 1968, 15, 125. A radical mechanism here is also possible.
4. 5), Kalinina, G. S.; Petrov, B. I.; Kruglaya, O. A.; Vyazankin, N. S. J. Gen. Chem. USSR (Engl. Transl.) 1972, 42, 144.
5. Doan, T. T.; Saudhu, G. S. U.S. Patents No. 5,278,100, 1994; 5,376,405, 1994; and 5,252,518, 1993.
6. (a) Smith, P. M.; Custer, J. S. Appl. Phys. Lett. 1997, 70, 3116.
7. (b) Reid, J. S.; Sun, X.; Kolawa, E.; Nicolet, M.-A. IEEE Electron Device Lett. 1994, 15, 298.
8. (c) Raaijmakers, I. J. Thin Solid Films 1994, 247, 85.
9. See Supporting Information for details.
10. For reactions of metal complexes with silanes and silyl chemistry see, for example: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175. (b) Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Part 2, Chapter 24. (c) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Chapter 10. (d) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; Wiley: New York, 1998; Part 3, Vol. 2, Chapter 35.
11. For reactions of metal complexes with silanes and silyl chemistry see, for example: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175. (b) Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Part 2, Chapter 24. (c) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Chapter 10. (d) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; Wiley: New York, 1998; Part 3, Vol. 2, Chapter 35.
12. For reactions of metal complexes with silanes and silyl chemistry see, for example: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175. (b) Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Part 2, Chapter 24. (c) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Chapter 10. (d) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; Wiley: New York, 1998; Part 3, Vol. 2, Chapter 35.
13. For reactions of metal complexes with silanes and silyl chemistry see, for example: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175. (b) Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Part 2, Chapter 24. (c) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Chapter 10. (d) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; Wiley: New York, 1998; Part 3, Vol. 2, Chapter 35.
14. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
15. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
16. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
17. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
18. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
19. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
20. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
21. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
22. 0 Cp-free silyl complexes, see: Xue, Z.; Li, L.; Hoyt, L. K.; Diminnie, J. B.; Pollitte, J. L. J. Am. Chem. Soc. 1994, 116, 2169. Li, L.; Diminnie, J. B.; Liu, X.; Pollitte, J. L.; Xue, Z. Organometallics 1996, 15, 3520. McAlexander, L. H.; Hung, M.; Li, L.; Diminnie, J. B.; Xue, Z.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1996, 15, 5231. Wu, Z.; Diminnie, J. B.; Xue, Z. Organometallics 1998, 17, 2917. Liu, X.; Li, L.; Diminnie, J. B,; Yap, G. P. A.; Rheingold, A. L.; Xue, Z. Organometallics 1998, 17, 4597. Chen, T.; Wu, Z.; Li, L.; Sorasaenee, K. R.; Diminnie, J. B.; Pan, H.; Guzei, I. A.; Rheingold, A. L.; Xue, Z. J. Am. Chem. Soc. 1998, 120, 13519. Wu, Z.; Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1999, 121, 4300. Xue, Z. Comments Inorg. Chem, 1996, 18, 223.
23. (a) Liu, H. Q.; Harrod, J. F. Organometallics 1992, 11, 822.
24. (b) Laine, R. M.; Blum, Y. D.; Tse, D.; Glaser, R. ACS Symp. Ser. 1988, 360, 124.
25. (c) Kinsley, K. K.; Nielson, T. J.; Barton, T. J. Main Group Met. Chem. 1987, 10, 307.
26. The Allred-Rochow electronegativities: H 2.20, N 3.07, Si 1.74, Ti(IV) 1.32, Zr(IV) 1.22. Huheey, J. E.; Keiter, E. A.; Keiler, R. L. Inorganic Chemistry, 4th ed.; Harper: New York, Collins, 1993.
27. (a) Fu et al. recently reported that the reactions of main group (tin) amides with silanes yielded hydrides and aminosilanes (Hays, D. S.; Fu, G. C. J. Org. Chem. 1997, 62, 7070).
28. 2 (Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1997, 119, 12657).
29. 2 (Diminnie, J. B.; Xue, Z. J. Am. Chem. Soc. 1997, 119, 12657).
30. Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784.
31. (a) Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363.
32. (b) Tilley, T. D. Acc. Chem. Res. 1993, 26, 22.
33. (c) Corey, J. Y. In Advances in Silicon Chemistry; Larson G., Ed.; JAI Press: Greenwich CT, 1991; Vol. 1, p 327.
34. (d) Casty, G. L.; Lugmair, C. G.; Radu, N. S.; Tilley, T. D.; Walzer, J. F.; Zargarian, D. Organometallics 1997, 16, 8.
35. (e) Bourg, S.; Corriu, R. J. P.; Enders, M.; Moreau, J. J. E. Organometallics 1995, 14, 564.
36. 2 with silanes, hydrides were isolated and characterized. See, for example: Mu, Y.; Aitken, C.; Cote, B.; Harrod, J. F.; Samuel, E. Can. J. Chem. 1991, 69, 264.
37. (a) Xin, S.; Aitken, C.; Harrod, J. F.; Mu, Y. Can. J. Chem. 1990, 68, 471.
38. (b) Woo, H. G. Ph.D. Thesis, University of California, San Diego, 1990.
39. For group 4 metallocene and heterometallic hydrides, see: (a) Hlatky, G. G.; Crabtree, R. H. Coord. Chem. Rev. 1985, 65, 1. (b) Toogood, G. E.; Wallbridge, M. G. H. Adv. Inorg. Chem. Radiochem. 1982, 25, 267.
40. For group 4 metallocene and heterometallic hydrides, see: (a) Hlatky, G. G.; Crabtree, R. H. Coord. Chem. Rev. 1985, 65, 1. (b) Toogood, G. E.; Wallbridge, M. G. H. Adv. Inorg. Chem. Radiochem. 1982, 25, 267.
41. (c) Wolczanski, P. T.; Bercaw, J. E. Acc. Chem. Res. 1980, 13, 121.
42. (d) Labinger, J. A. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992; pp 361-387.
43. (e) Etkin, N.; Hoskin, A. J.; Stephan, D. W. J. Am. Chem. Soc. 1997, 119, 11420.
44. (f) Hart, D. W.; Schwartz, J. J. Am. Chem. Soc. 1974, 96, 8115.
45. (a) Basch, H.; Musaev, D. G.; Morokuma, K.; Fryzuk, M. D.; Love, J. B.; Seidel, W. W.; Albinati, A.; Koetzle, T. F.; Klooster, W. T.; Mason, S. A.; Eckert, J. J. Am. Chem. Soc. 1999, 121, 523.
46. (b) Nöth, H.; Schmidt, M. Organometallics 1995, 14, 4601.
47. (c) Jacoby, D.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. J. Am. Chem. Soc. 1993, 175, 3595.
48. (a) Gozum, J. E.; Girolami, G. S. J. Am. Chem. Soc. 1991, 113, 3829.
49. (b) Gozum, J. E.; Wilson, S. R.; Girolami, G. S. J. Am. Chem. Soc. 1992, 114, 9483.
50. (c) Mayo, S. C.; Bown, M.; Lloyd, V. K. Acta Crystallogr. 1994, C50, 367.
51. (d) Fryzuk, M. D.; Rettig, S. J.; Westerhaus, A.; Williams, H. D. Inorg. Chem. 1985, 24, 4316.
52. 17a
53. (a) Oka, A. Bull. Chem. Soc. Jpn. 1967, 40, 2284.
54. (b) The Merck Index, 12th ed; Merck: Whitehouse Station, NJ, 1996.
55. 4 in Kr and Ar matrices at 12 K has been characterized by IR. Xiao, Z. L.; Hauge, R. H.; Margrave, J. L. J. Phys. Chem. 1991, 95, 2696.
56. 3 has been reported. Tebbe, F. N. U.S. Patent 3933876, 1976.
57. (a) Corker, J.; Lefebvre, F.; Lécuyer, C.; Dufaud, V.; Quignard, F.; Choplin, A.; Evans, J.; Basset, J.-M. Science 1996, 271, 966.
58. (b) Cummins, C. C.; Schrock, R. R.; Davis, W. M. Organometallics 1992, 11, 1452.
59. Jones, S. B.; Petersen, J. L. Inorg. Chem. 1981, 20, 2889.
60. See, for example: Wu, Z.; Diminnie, J. B.; Xue, Z. Inorg. Chem. 1998, 37, 2570.