Oxidation of 2-pyridyldimethylsilyl group to hydroxyl group by H2O2/KF. Implication of fluoride ion accelerated 2-pyridyl-silyl bond cleavage

Journal of Organic Chemistry

Volumn 64, Issue 23, 1999, Pages 8709-8714

  Itami, Kenichiro ^a   Mitsudo, Koichi ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SILANE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CONFORMATIONAL TRANSITION; DEGRADATION; ELECTRON TRANSPORT; OXIDATION; SYNTHESIS;

EID: 0033550160     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990740u     Document Type: Article

References (64)

1. For excellent reviews on the oxidative cleavage of silicon-carbon bond, see: (a) Tamao, K. Advances in Silicon Chemistry; JAI Press Inc.: Greenwich, CT, 1996; Vol. 3, p 1. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
2. For excellent reviews on the oxidative cleavage of silicon-carbon bond, see: (a) Tamao, K. Advances in Silicon Chemistry; JAI Press Inc.: Greenwich, CT, 1996; Vol. 3, p 1. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
3. (a) Ager, D. J. Tetrahedron Lett. 1980, 21, 4759.
4. (b) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217.
5. (a) Stork, G.; Colvin, E. J. Am. Chem. Soc. 1971, 93, 2080.
6. (b) Büchi, G.; Wüest, H. J. Am. Chem. Soc. 1978, 100, 294.
7. (c) Cunico, R. F. J. Organomet. Chem. 1981, 212, C51.
8. (d) Kuwajima, I.; Urabe, H. Tetrahedron Lett. 1981, 22, 5191.
9. (e) Fleming, I.; Newton, T. W. J. Chem. Soc., Perkin Trans. 1 1984, 119.
10. (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947.
11. (a) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660.
12. (b) Wilson, S. R., Augelli-Szafran, C. E. Tetrahedron 1988, 44, 3983.
13. (c) Fujii, T.; Hirao, T.; Ohshiro, Y. Tetrahedron Lett. 1993, 34, 5601.
14. (a) Yoshida, J.; Murata, T.; Isoe, S. Tetrahedron Lett. 1986, 27, 3373.
15. (b) Koizumi, T.; Fuchigami, T.; Nonaka, T. Chem. Express 1986, 1, 355.
16. (c) Yoshida, J.; Murata, T.; Isoe, S. Tetrahedron Lett. 1987, 28, 211.
17. (d) Yoshida, J.; Murata, T.; Isoe, S. J. Organomet. Chem. 1988, 345, C23.
18. (e) Koizumi, T.; Fuchigami, T.; Nonaka, T. Bull. Chem. Soc. Jpn. 1989, 62, 219.
19. (f) Yoshida, J.; Maekawa, T.; Murata, T.; Matsunaga, S.; Isoe, S. J. Am. Chem. Soc. 1990, 112, 1962.
20. (g) Yoshida, J. Topics Curr. Chem. 1994, 170, 39.
21. (h) Yoshida, J. J. Synth. Org. Chem., Jpn. 1995, 53, 69.
22. Mizuno, K.; Yasueda, M.; Otsuji, Y. Chem. Lett. 1988, 229.
23. (a) Müller, R. Organometal. Chem. Rev. 1966, 1, 359.
24. (b) Tamao, K.; Kakui, T.; Kumada, M. J. Am. Chem. Soc. 1978, 100, 2268.
25. (c) Tamao, K.; Yoshida, J.; Kumada, M. J. Synth. Org. Chem., Jpn. 1980, 38, 769.
26. (d) Kumada, M.; Tamao, K.; Yoshida, J. J. Organomet. Chem. 1982, 239, 115.
27. (e) Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983.
28. (a) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694.
29. (b) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
30. (c) Tamao, K.; Kumada, M.; Maeda, K. Tetrahedron Lett. 1984, 25, 321.
31. (d) Tamao, K.; Maeda, K. Tetrahedron Lett. 1986, 27, 65.
32. (e) Tamao, K.; Nakajima, T.; Sumiya, R.; Arai, H.; Higuchi, N.; Ito, Y. J. Am. Chem. Soc. 1986, 108, 6090.
33. (f) Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 957.
34. (g) Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 4412.
35. (h) Tamao, K.; Yamauchi, T.; Ito, Y. Chem. Lett. 1987, 171.
36. (i) Tamao, K.; Nakagawa, Y.; Arai, H.; Higuchi, N.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 3712.
37. (j) Tamao, K. J. Synth. Org. Chem., Jpn. 1988, 46, 861.
38. (k) Tamao, K.; Ishida, N.; Ito, Y.; Kumada, M. Org. Synth. 1990, 69, 96.
39. (a) Fleming, I.; Henning, R.; Plaut, H. Chem. Commun. 1984, 29.
40. (b) Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317.
41. (a) Fleming, I.; Ghosh, S. K. Chem. Commun. 1992, 1775.
42. (b) Fleming, I.; Ghosh, S. K. Chem. Commun. 1992, 1777.
43. (a) Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731.
44. (b) Knölker, H.; Wanzl, G. Synlett 1995, 378.
45. (a) Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4249.
46. (b) Magar, S. S.; Desai, R. C.; Fuchs, P. L. J. Org. Chem. 1992, 57, 5360.
47. (a) Fleming, I.; Winter, S. B. D. Tetrahedron Lett. 1993, 34, 7287.
48. (b) Fleming, I.; Winter, S. B. D. Tetrahedron Lett. 1995, 36, 1733.
49. Stork, G. Pure Appl. Chem. 1989, 61, 439.
50. Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501.
51. Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1995, 36, 2987.
52. (a) Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737.
53. (b) Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
54. van Delft, F. L.; van der Marel, G. A.; van Boom, J. H. Synlett 1995, 1069.
55. Angelaud, R.; Landais, Y.; Maignan, C. Tetrahedron Lett. 1995, 36, 3861.
56. (a) Krohn, K.; Khanbabaee, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 99.
57. (b) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941.
58. Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994.
59. Yoshida, J.; Itami, K.; Mitsudo, K.; Suga, S. Tetrahedron Lett. 1999, 40, 3403.
60. Alternatively, one could expect that the oxidation of the pyridyl group first occurs to give the corresponding N-oxide, which can then undergo β-elimination to give 4 and 2-hydroxypyridine or 2-methoxypyridine. However, none of these products except 4 were detected in the reaction mixture, which suggests that the mechanism involving N-oxide β-elimination is not the case.
61. (a) Anderson, D. G.; Bradney, M. A. M.; Webster, D. E. J. Chem. Soc. (B) 1968, 450.
62. (b) Anderson, D. G.; Webster, D. E. J. Chem. Soc. (B) 1968, 765.
63. (c) Anderson, D. G.; Webster, D. E. J. Chem. Soc. (B) 1968, 1008.
64. The ab initio molecular orbital calculations were carried out at the MP2/LANL2DZ level with geometry optimization using Gaussian 98, Revision A.6.: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.