Catalytic oxidation adjacent to carbonyl groups and at benzylic positions with a fluorous seleninic acid in the presence of iodoxybenzene

Journal of Organic Chemistry

Volumn 70, Issue 8, 2005, Pages 3309-3311

  Crich, David ^a   Zou, Yekui ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; KETONES; OXIDATION;

CARBONYL GROUPS; CATALYTIC OXIDATION; IODOXYBENZENE; KETOACIDS;

AROMATIC COMPOUNDS;

(2 BROMOPHENYL)GLYOXYLIC ACID; (4 METHOXYPHENYL)GLYOXYLIC ACID; 1 NAPHTHYLGLYOXYLIC ACID; BENZENE DERIVATIVE; BUTYL PERFLUOROOCTYL SELENIDE; DI(PERFLUOROOCTYL) DISELENIDE; DIBUTYL DISELENIDE; GLYOXYLIC ACID DERIVATIVE; IODYLBENZENE; PERFLUOROOCTYLSELENINIC ACID; PHENYLGLYOXYLIC ACID; PHENYLMALEIC ANHYDRIDE; SELENIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; STOICHIOMETRY; SYNTHESIS;

EID: 17444381576     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0500333     Document Type: Article

References (31)

1. For example see: (a) Modern Oxidation Methods; Bäckvall, J.-E., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
2. (a) Crich, D.; Neelamkavil, S. J. Am. Chem. Soc. 2001, 123, 7449.
3. (b) Crich, D.; Neelamkavil, S. Tetrahedron 2002, 58, 3865.
4. (a) Crich, D.; Barba, G. R. Org. Lett. 2000, 2, 989.
5. (b) Crich, D.; Neelamkavil, S.; Sartillo-Piscil, F. Org. Lett. 2000, 2, 4029.
6. (a) Betzemeier, B.; Lhermitte, F.; Knochel, P. Synlett 1999, 489.
7. (b) ten Brink, G.-J.; Vis, M.; Arend, I. W. C. E.; Sheldon, R. A. Tetrahedron 2002, 58, 3977.
8. Reviews on fluorous supported oxidations: (a) Crich, D.; Zou, Y. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 202. (b) Pozzi, G.; Quici, S. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 290. (c) Vincent, J.-M.; Lastécouères, D.; Contel, M.; Laguna, M.; Fish, R. H. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 298. (d) Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 341.
9. Reviews on fluorous supported oxidations: (a) Crich, D.; Zou, Y. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 202. (b) Pozzi, G.; Quici, S. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 290. (c) Vincent, J.-M.; Lastécouères, D.; Contel, M.; Laguna, M.; Fish, R. H. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 298. (d) Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 341.
10. Reviews on fluorous supported oxidations: (a) Crich, D.; Zou, Y. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 202. (b) Pozzi, G.; Quici, S. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 290. (c) Vincent, J.-M.; Lastécouères, D.; Contel, M.; Laguna, M.; Fish, R. H. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 298. (d) Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 341.
11. Reviews on fluorous supported oxidations: (a) Crich, D.; Zou, Y. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 202. (b) Pozzi, G.; Quici, S. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 290. (c) Vincent, J.-M.; Lastécouères, D.; Contel, M.; Laguna, M.; Fish, R. H. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 298. (d) Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 341.
12. Crich, D.; Zou, Y. Org. Lett. 2004, 6, 775.
13. For a discussion of allylic oxidation with seleninic acids see: Ley, S. V. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley: New York, 1987; p 163.
14. The exceptions here are 2-pyridineseleninic acid, the unstable 2-pyridineseleninic acid N-oxide, and pentafluorobenzeneseleninic acid, each of which effect allylic oxidation: (a) Barton, D. H. R.; Crich, D. Tetrahedron 1985, 41, 4359. (b) Barton, D. H. R.; Wang, T.-L. Tetrahedron Lett. 1994, 35, 5149.
15. The exceptions here are 2-pyridineseleninic acid, the unstable 2-pyridineseleninic acid N-oxide, and pentafluorobenzeneseleninic acid, each of which effect allylic oxidation: (a) Barton, D. H. R.; Crich, D. Tetrahedron 1985, 41, 4359. (b) Barton, D. H. R.; Wang, T.-L. Tetrahedron Lett. 1994, 35, 5149.
16. Magnier, E.; Vit, E.; Wakselman, C. Synlett 2001, 1260.
17. (a) Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450.
18. (b) Maul, J. J.; Ostrowski, P. J.; Ublacker, G. A.; Linclau, B.; Curran, D. P. Top. Curr. Chem. 1999, 206, 79.
19. (c) Gladysz, J. A.; Emnet, C. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 11.
20. The reduction step is to facilitate recovery of the fluorous reagent: diselenide 2 dissolves readily in organic and fluorous solvents whereas the amorphous seleninic acid is poorly soluble and so is not accessible to an extractive workup and separation.
21. Crich, D.; Hao, X.; Lucas, M. Tetrahedron 1999, 55, 14261.
22. Barton, D. H. R.; Morzycki, J. W.; Motherwell, W. B.; Ley, S. V. J. Chem. Soc., Chem. Commun. 1981, 1044.
23. (a) Hu, X. B.; Tian, Z. J.; Lu, X. R. Synth. Commun. 1997, 27, 553.
24. (b) Salama, P.; Bernard, C. Tetrahedron Lett. 1995, 36, 5571.
25. Taylor, G. C.; Strojny, E. J. J. Am. Chem. Soc. 1954, 76, 1872.
26. Gross, H.; Freiberg, J. Chem. Ber. 1967, 100, 3777.
27. Raap, R. Tetrahedron Lett. 1969, 40, 3493.
28. Eastman, J. F.; Selman, S. J. Org. Chem. 1961, 26, 293.
29. Russanow, A. Chem. Ber. 1892, 25, 3298.
30. Rapoport, E.; Cass, M. W.; White, E. H. J. Am. Chem. Soc. 1992, 94, 3160.
31. Barton, D. H. R.; Finet, J. P.; Thomas, M. Tetrahedron 1988, 44, 6397.