A series of new hypervalent iodine reagents based on the 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole and 1,2-benziodoxol-3-(1H)-one scaffolds, which contain a functionalized tetrafluoroethyl group, have been prepared, characterized, and used in synthetic applications. Their corresponding electrophilic fluoroalkylation reactions with various sulfur, oxygen, phosphorus, and carbon-centered nucleophiles afford products that feature a tetrafluoroethylene unit, which connects two functional moieties. A related λ(3) -iodane that contains a fluorophore was shown to react with a cysteine derivative under mild conditions to give a thiol-tagged product that is stable in the presence of excess thiol. Therefore, these new reagents show a significant potential for applications in chemical biology as tools for fast, irreversible, and selective thiol bioconjugation.

Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zürich Vladimir Prelog Weg 2 8093 Zürich

Institute of Organic Chemistry and Biochemistry v v i Academy of Sciences of the Czech Republic Flemingovo nám 2 166 10 Prague

Laboratory of Molecular Structure Characterization Institute of Microbiology v v i Academy of Sciences of the Czech Republic Vídeňská 1083 142 20 Prague

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