Issue 12, 2005

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

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

Supplementary files

Article information

Article type
Communication
Submitted
22 Aug 2005
Accepted
19 Oct 2005
First published
26 Oct 2005

Green Chem., 2005,7, 833-836

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements