Ruthenium-catalyzed oxidation of secondary alcohols assisted by a simple alkene

Bulletin of the Korean Chemical Society

Volumn 26, Issue 5, 2005, Pages 802-804

  Cho, Chan Sik ^a   Kim, Dae Yong ^a   Shim, Sang Chul ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Hydrogen acceptor; Ketones; Oxidation; Ruthenium catalyst; Secondary alcohols

Indexed keywords

EID: 20444458390     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2005.26.5.802     Document Type: Article

References (22)

1. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
2. For ruthenium-catalyzed oxidation of alcohols with co-oxidants: (a) Sharpless, K. B.; Akashi, K.; Oshima, K. Tetrahedron Lett. 1976, 2503.
3. (b) Tang, R.; Diamond, S. E.; Meary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562.
4. (c) Matsumoto, M.; Ito, S. J. Chem. Soc., Chem. Commun. 1981, 907.
5. (d) Müller, P.; Godoy, J. Tetrahedron Lett. 1981, 22, 2361.
6. (e) Tsuji, Y.; Ohta, T.; Ido, T.; Minbu, H. J. Organomet. Chem. 1984, 270, 333.
7. (f) Yamamoto, Y.; Suzuki, H.; Moro-oka, Y. Tetrahedron Lett. 1985, 26, 2107.
8. (g) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
9. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Tetrahedron Lett. 2002, 43, 7987.
10. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Org. Chem. 2001, 66, 9022.
11. Cho, C. S.; Kim, B. T.; Kim, H.-S.; Kim, T.-J.; Shim, S. C. Organometallics 2003, 22, 3608.
12. 3 (2 mol%)/KOH (1 equiv.)/1-dodecene (1 equiv.)/ dioxane/80 °C/20 h gave 1,3-diphenylpropan-1-one and 1,3-diphenylpropan-1-ol in 82% and 2% isolated yields, respectively. On the other hand, when the reaction was carried out in the absence of 1-dodecene, 1,3-diphenylpropan-1-one was formed in 70% yield along with considerable amount of 1,3-diphenylpropan-1-ol(14%).
13. For similar enhancement of ruthenium-catalyzed oxidative cyclization between 2-aminobenzyl alcohol and secondary alcohols by the addition of 1-dodecene: Cho, C. S.; Kim, B. T.; Choi, H.-J.; Kim, T.-J.; Shim, S. C. Tetrahedron 2003, 59, 7997.
14. For recent reviews on transition metal-catalyzed transfer hydrogenation, see: (a) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
15. (b) Bäckvall, J.-E.; Chowdhury, R. L.; Karlsson, U.; Wang, G. In Perspectives in Coordination Chemistry; Williams, A. F.; Floriani, C.; Merbach, A. E., Eds.; VCH: New York, 1992; pp 463-486.
16. (c) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
17. (d) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
18. (e) Palmer, M.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045.
19. (a) Sasson, Y.; Blum, J. Tetrahedron Lett. 1971, 2167.
20. (b) Regen, S. L.; Whitesides, G M. J. Org. Chem. 1972, 37, 1832.
21. Similar treatment of 3a in the presence of benzalacetone in place of 1 -dodecene afforded 4a in 73% yield with 89% conversion of 3a (run 6 of Table 1).
22. For ruthenium-catalyzed isomerization of allylic alcohols to saturated aldehydes and ketones: Sasson, Y.; Rempel, G. L. Tetrahedron Lett. 1974, 4133.