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Volumn 6, Issue 5, 2004, Pages 775-777

Catalytic allylic oxidation with a recyclable, fluorous seleninic acid

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZENE DERIVATIVE; BENZOTRIFLUORIDE; BIS(PERFLUOROOCTYL)DISELENIDE; FLUORINE DERIVATIVE; IODYLBENZENE; KETONE DERIVATIVE; PERFLUOROOCTYLSELENINIC ACID; SELENIUM DERIVATIVE; SODIUM METABISULFITE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 1642373794     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036501h     Document Type: Article
Times cited : (55)

References (28)
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    • Trost, B. M., Ed.: Pergamon: Oxford, UK
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    • (b) 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.
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    • note
    • The insertion of a reduction into the workup is to facilitate recovery of the fluorous reagent - diselenide 8 dissolves readily in organic and fluorous solvents whereas the amorphous seleninic acid is poorly soluble and so not accessible to an extractive workup and separation.
  • 26
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    • note
    • The 3,5-disubstituted system also catalyzes the Baeyer-Villiger oxidation of cyclobutanone. 15b
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    • For a collection of articles on fluorous reagents and catalysts see: Curran, D. P.; Gladysz, J. A., Eds. Tetrahedron 2002, 55, 3823.
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    • Curran, D.P.1    Gladysz, J.A.2
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    • In a similar vein we have also reported the development of a fluorous version of borane dimethyl sulfide in which the fluorous chain serves the dual purposes of facilitating purification/recycling and of rendering the borane air stable: Crich, D.; Neelamkavil, S. Org. Lett. 2002, 4, 4175.
    • (2002) Org. Lett. , vol.4 , pp. 4175
    • Crich, D.1    Neelamkavil, S.2


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