An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF 3 (CF 2 ) n−1 I(OCOCF 3 ) 2
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Reactions of commercial fluorous alkyl iodides RfnI (1-R fn; 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-R f10 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-R fn and reused. © The Royal Society of Chemistry 2005.
author list (cited authors)
Tesevic, V., & Gladysz, J. A.