Benzodithiazoles-Sulfoximines: Preparation, Properties and Reactivities as Radical Perfluoroalkylating Agents

We describe the preparation of S-perfluoroalkyl benzodithiazole trioxides as radical perfluoroalkylating reagents. Their syntheses were performed on a multi-gram scale by an oxidative cyclization connecting the nitrogen of a sulfoximine and a sulfur atom previously introduced in the ortho position of this group. The structures and properties of these new molecules were carefully examined by X-Ray diffraction, DFT calculations and cyclic voltammetry. These data clearly highlight the enhanced reactivity of these cyclic sulfoximines compared to their open analogues. This was confirmed by photoredox catalysis experiments that revealed interesting reactivity, most especially for the introduction of di- and monofluoroalkyl chains.

Automated summary

We prepared S-perfluoroalkyl benzodithiazole trioxides as radical perfluoroalkylating reagents. The synthesis of these compounds was achieved on a multi-gram scale through oxidative cyclization. The structures and properties of the molecules were investigated using X-Ray diffraction, DFT calculations, and cyclic voltammetry. The enhanced reactivity of the cyclic sulfoximines compared to their open analogues was confirmed by photoredox catalysis experiments.