Highly Efficient Iridium-Catalyzed Oxidation of Organosilanes to Silanols

Journal of Organic Chemistry

Volumn 69, Issue 5, 2004, Pages 1741-1743

  Lee, Youngjun ^a   Seomoon, Dong ^a   Kim, Sundae ^a   Han, Hoon ^b   Chang, Sukbok ^b   Lee, Phil Ho ^a  

^a Kangwon National University   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; IRIDIUM; OXIDATION; SILANES;

CATALYST SYSTEMS; SILANOLS;

ORGANIC COMPOUNDS;

IRIDIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; HYDROLYSIS; OXIDATION; POLYMERIZATION; SYNTHESIS;

EID: 1442348921     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035647r     Document Type: Article

References (39)

1. (a) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. Chem. Commun. 1993, 436.
2. (b) Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60.
3. (c) Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 6781.
4. (d) Uehira, S.; Takaku, K.; Shinokubo, H.; Oshima, K. Synlett 1998, 1096.
5. Lickiss, P. D. Adv. Inorg. Chem. 1995, 42, 147.
6. (a) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893.
7. (b) Hirabayashi, K.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Org. Lett. 1999, 1, 299.
8. (c) Denmark, S. E.; Wehrli, D. Org. Lett. 2990, 2, 565.
9. (d) Chang, S.; Yang, S. H.; Lee, P. H. Tetrahedron Lett. 2001, 42, 4883.
10. (a) Rochow, E. G.; Gilliam, W. F. J. Am. Chem. Soc. 1941, 63, 798.
11. (b) Sauer, R. O. J. Am. Chem. Soc. 1944, 66, 1707.
12. Adam, W.; Mello, R.; Curci, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 890.
13. (a) Sieburth, S. M.; Mu, W. J. Org. Chem. 1993, 58, 7584.
14. (b) Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461.
15. (a) Sommer, L. H.; Lyons, J. E. J. Am. Chem. Soc. 1989, 91, 7061.
16. (b) Matarasso-Tchiroukhine, E. Chem. Commun. 1990, 681.
17. (c) Egger, C.; Schubert, U. Z. Naturforsch., B 1991, 46, 783.
18. (d) Schubert, U.; Lorenz, C. Inorg. Chem. 1997, 36, 1258.
19. Lee, M.; Ko, S.; Chang, S. J. Am. Chem. Soc. 2000, 122, 12011.
20. (a) Lee, P. H.; Bang, K.; Lee, K.; Lee, C.-H.; Chang, S. Tetrahedron Lett. 2000, 41, 7521.
21. (b) Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887.
22. (c) Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887.
23. (d) Lee, P. H.; Lee, K.; Kim, S. Org. Lett. 2001, 3, 3205.
24. (e) Lee, P. H.; Lee, K.; Sung, S.-Y.; Chang, S. J. Org. Chem. 2001, 66, 8646.
25. (f) Lee, P. H.; Ahn, H.; Lee, K.; Sung, S.-Y.; Kim, S. Tetrahedron Lett. 2001, 42, 37.
26. (g) Lee, P. H.; Bang, K.; Ahn, H.; Lee, K. Bull. Korean Chem. Soc. 2001, 22, 1385.
27. (h) Choi, E.; Lee, C.; Na, Y.; Chang, S. Org. Lett. 2002, 4, 2369.
28. (i) Lee, P. H.; Seomoon, D.; Lee, K.; Heo, Y. J. Org. Chem. 2003, 68, 2510.
29. (j) Lee, P. H.; Seomoon, D.; Kim, S.; Nagaiah, S. V.; Damle, S. V.; Lee, K. Synthesis 2003, 2189.
30. (a) Schubert, U.; Lorenz, C. Inorg. Chem. 1997, 36, 1258.
31. (b) Shi, M. M.; Nicholas, K. M. J. Chem. Res., Synop. 1997, 400.
32. (c) Adam, W.; Garcia, H.; Mitchell, C. M.; Saha-Moller, C. R.; Weichold, O. Chem. Commun. 1998, 2609.
33. (d) Adam, W.; Mitchell, C. M.; Saha-Moller, C. R.; Weichold, O. J. Am. Chem. Soc. 1999, 121, 2097.
34. (e) Coupar, P. I.; Jaffres, P.-A.; Morris, R. E. J. Chem. Soc., Dalton Trans. 1999, 2183.
35. Herde, J. L.; Lambert, J. C.; Senoff, C. V. Inorg. Synth. 1974, 15, 18.
36. Alkenyl- and alkynylsilanes were readily prepared in good yields by the reaction of a chlorodialkylsilane with lithiated alkenes and alkynes, respectively (for details, see ref 8).
37. Sommer, L. H.; Frye, C. L.; Parker, G. A.; Michael, K. W. J. Am. Chem. Soc. 1964, 86, 3271.
38. (a) Sommer, L. H.; Lyons, J. E. J. Am. Chem. Soc. 1969, 91, 7061.
39. (b) Sommer, L. H.; Ulland, L. A.; Parker, G. A. J. Am. Chem. Soc. 1972, 94, 3469.