Unexpected reactivity of cyclic perfluorinated iodanes with electrophiles

Stefan Gruber; Simon M Ametamey; Roger Schibli

doi:10.1039/c8cc04558e

Unexpected reactivity of cyclic perfluorinated iodanes with electrophiles

Chem Commun (Camb). 2018 Aug 9;54(65):8999-9002. doi: 10.1039/c8cc04558e.

Authors

Stefan Gruber¹, Simon M Ametamey, Roger Schibli

Affiliation

¹ Institute of Pharmaceutical Sciences, Department of Chemistry and Applied Biosciences, ETH Zurich Vladimir-Prelog-Weg 4, Zurich 8093, Switzerland. stefan.gruber@pharma.ethz.ch.

PMID: 30027951
DOI: 10.1039/c8cc04558e

Abstract

We have found that cyclic perfluorinated iodanes react with electrophiles (E+ = Br, Cl, F, I) to afford perfluorinated E-RF compounds. This reactivity is unexpected since cyclic perfluorinated iodanes are considered as electrophilic reagents that normally react with nucleophiles (e.g. Nu- = SR, OR) to afford Nu-RF products. The utility of this new transformation is demonstrated for a [18F]CF3CF2-containing compound which was prepared from [18F]XeF2 obtained from cyclotron produced [18F]fluoride.