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Issue 12, 2005
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An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)n−1I(OCOCF3)2

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Abstract

Reactions of commercial fluorous alkyl iodides RfnI (1-Rfn; Rfn = CF3(CF2)n−1; n = 7, 8, 10, 12) with 80% H2O2 and trifluoroacetic anhydride give RfnI(OCOCF3)2 (2-Rfn; 89–97%). These rapidly oxidize 1,4-hydroquinones in methanol. Subsequent additions of CF3C6F11 or FC-72 give liquid/liquid biphase systems. The product quinones are generally isolated in ≥95% yields from the methanol phases, and 1-Rfn in ≥95% yields from the fluorous phases. Alternatively, the very low solubilities of 1-Rf10 in 10 ∶ 1 v/v methanol ∶ water or 1-Rf12 in methanol allow efficient recovery via solid/liquid phase separations without recourse to fluorous solvents. The recovered 1-Rfn may be reoxidized to 2-Rfn and reused.

Graphical abstract: An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)n−1I(OCOCF3)2

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Publication details

The article was received on 22 Aug 2005, accepted on 19 Oct 2005 and first published on 26 Oct 2005


Article type: Communication
DOI: 10.1039/B511951K
Citation: Green Chem., 2005,7, 833-836
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    An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)n−1I(OCOCF3)2

    V. Tesevic and J. A. Gladysz, Green Chem., 2005, 7, 833
    DOI: 10.1039/B511951K

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