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Merging hypervalent iodine and sulfoximine chemistry: a new electrophilic trifluoromethylation reagent

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Abstract

Electrophilic trifluoromethylation is at the forefront of methodologies available for the installation of the CF3 moiety to organic molecules; research in this field is largely spurred by the availability of stable and accessible trifluoromethylation reagents, of which hypervalent iodine and sulfoximine based compounds have emerged as two prominent reagent classes. Herein, we describe the facile synthesis of an electrophilic trifluoromethylation reagent which merges these two scaffolds in a novel hypervalent iodosulfoximine compound. This presents the first analogue of the well-known Togni reagents which neither compromises stability or reactivity. The electronic and physical properties of this new compound were fully explored by X-ray crystallography, cyclic voltammetry, TGA/DSC and DFT analysis. This solution stable, crystalline reagent was found to be competent in the electrophilic trifluoromethylation of a variety of nucleophiles as well as a source of the trifluoromethyl radical. Furthermore, the possibility of enantioinductive transformations could be probed with the isolation of the first enantiopure hypervalent iodine compound bearing a CF3 group, thus this new reagent scaffold offers the opportunity of structurally diversifying the reagent towards asymmetric synthesis.

Graphical abstract: Merging hypervalent iodine and sulfoximine chemistry: a new electrophilic trifluoromethylation reagent

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Publication details

The article was received on 25 Aug 2019, accepted on 20 Sep 2019 and first published on 27 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC04289J
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Merging hypervalent iodine and sulfoximine chemistry: a new electrophilic trifluoromethylation reagent

    J. Kalim, T. Duhail, T. Le, N. Vanthuyne, E. Anselmi, A. Togni and E. Magnier, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC04289J

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