Cobalt phthalocyanine catalyzed aerobic oxidation of secondary alcohols: An efficient and simple synthesis of ketones

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 383-386

  Sharma, Vishal B ^a   Jain, Suman L ^a   Sain, Bir ^a  

^a CSIR INDIAN INSTITUTE OF PETROLEUM   (India)

Author keywords

Cobalt phthalocyanine; Ketones; Molecular oxygen; Oxidation; Secondary alcohols

Indexed keywords

ALCOHOL DERIVATIVE; COBALT DERIVATIVE; KETONE DERIVATIVE; OXYGEN; PHTHALOCYANINE COBALT; PHTHALOCYANINE DERIVATIVE; POTASSIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; OXIDATION; SYNTHESIS;

EID: 0037421036     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02453-X     Document Type: Article

References (38)

1. Sheldon R.A., Kochi J.K. Metal Catalyzed Oxidations of Organic Compounds. 1981;Academic Press, London.
2. Ley S.V., Madin A. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 7:1991;305-327 Pergamon, Oxford.
3. Cainelli G., Cardillo G. Chromium Oxidants in Organic Chemistry. 1984;Springer, Berlin.
4. Ley S.V., Madin A. Trost B.M., Fleming I., Ley S.V. Comprehensive Organic Synthesis. 7:1991;251-289 Pergamon, Oxford, UK.
5. Nishiyama Y., Nakagawa Y., Mizuno N. Angew. Chem., Int. Ed. 40:2001;3639.
6. Thomas J.M., Raja R., Sankar K., Bell R.G. Acc. Chem. Res. 34:2001;191.
7. Dobler C., Mehltretter G.M., Sundermeier U., Beller M. J. Am. Chem. Soc. 122:2001;10289.
8. David R.J., Pugsley S.J., Matthew S. J. Am. Chem. Soc. 123:2001;7475.
9. Davis S., Drago R.S. J. Chem. Soc., Chem. Commun. 1990;250.
10. Tang R., Diamond S.E., Neary N., Mares F. J. Chem. Soc., Chem. Commun. 1978;562.
11. Matsumoto M., Watanabe N. J. Org. Chem. 49:1984;3435.
12. Backvall J.E., Chowdhury R.L., Karlsson U. J. Chem. Soc., Chem. Commun. 1991;473.
13. Backvall J.E., Awasthi A.K., Renko Z.D. J. Am. Chem. Soc. 109:1987;4750.
14. Backvall J.E., Hopkins R.B. Tetrahedron Lett. 29:1988;2885.
15. Backvall J.E., Hopkins R.B., Grinnberg H., Mader M., Awasthi A.K. J. Am. Chem. Soc. 112:1990;5160.
16. Marko I.E., Giles P.R., Tsukazaki M., Chelle-Regnaut I., Urch C.J., Brown S.M. J. Am. Chem. Soc. 119:1997;12661.
17. Yamaguchi K., Mori K., Mizugaki T., Ebitani K., Kaneda K. J. Am. Chem. Soc. 122:2000;7144.
18. Csjernyik G., Ell A.H., Fadini I., Pugin B., Backvall J.E. J. Org. Chem. 67:2002;1657.
19. Kaneda K., Yamashita T., Matsushita T., Ebitani K. J. Org. Chem. 63:1998;1750.
20. Kakiuchi N., Maeda Y., Nishimura T., Uemura S. J. Org. Chem. 66:2001;6620.
21. Kalra S.J.S., Punniyamurthy T., Iqbal J. Tetrahedron Lett. 35:1994;4847.
22. Perollier C., Sorokin A.B. Chem. Commun. 2002;1548.
23. Meunier B., Sorokin A. Acc. Chem. Res. 30:1997;470.
24. Sorokin A., De Suzzoni-Dezard S., Poullain D., Noel J.P., Meunier B. J. Am. Chem. Soc. 118:1996;7418.
25. Hadasch A., Sorokin A., Rabion A., Fraisse L., Meunier B. Bull. Soc. Chim. Fr. 134:1997;1025.
26. Sorokin A., Meunier B. J. Chem. Soc., Chem. Commun. 1994;1799.
27. Sorokin A., Seris J.L., Meunier B. Science. 268:1995;1163.
28. Kasuga K., Mori K., Sugimori T., Handa M. Bull. Chem. Soc. Jpn. 73:2000;939.
29. Grootboom N., Nyokong T. J. Mol. Catal. 179:2002;113.
30. Jain S.L., Sain B. Chem. Commun. 2002;1040.
31. Jain S.L., Sain B. J. Mol. Catal. 176:2001;101.
32. Rao T.V., Sain B., Kumar K., Murthy P.S.N., Prasada Rao T.S.R., Joshi G.C. Synth. Commun. 28:1998;319.
33. Sain B., Murthy P.S.N., Rao T.V., Prasada Rao T.S.R., Joshi G.C. Tetrahedron Lett. 35:1994;5083.
34. Rao T.V., Sain B., Murthy P.S., Prasada Rao T.S.R., Jain A.K., Joshi G.C. J. Chem. Res. (S). 1997;300.
35. Rao T.V., Sain B., Murthy P.S.N., Joshi G.C., Prasada Rao T.S.R. Stud. Surf. Sci. Catal. 113:1998;921.
36. 2). At the end of reaction cobalt phthalocyanine and powdered potassium hydroxide were removed by filtration. The filtrate obtained was evaporated under vacuum and the residue thus obtained was purified by column chromatography on silica gel using ethyl acetate/hexane (1:4) as eluent. Evaporation of the solvent yielded benzophenone (171 mg, 94%). Other alcohols were oxidized using this procedure and their reaction times and yields are given in Table 1. The products were identified by comparing their physical and spectral data with those of authentic compounds reported in literature.
37. Agrawal B.B., Fish S.F., Puri S.N., Gupta P., Joshi G.C., Krishna R. Ind. J. Technol. 25:1987;397.
38. Acher B.N., Fohlen G.M., Parker J.A., Keshavayya J. Ind. J. Chem. 27A:1988;411.