Redox Chemistry towards an Access to Polyfluorinated Alkylamines – RedAF

Organofluorine chemistry became a research of paramount importance as fluorinated molecules are prevalent derivatives in pharmaceutical, agrochemical industries and material sciences. Of particular relevance is the emergence of trifluoromethylated alkylamines. Indeed, the trifluoromethyl moiety near the nitrogen center can have a deep impact on the physicochemical and biological properties of alkylamines such as metabolic stability, lipophilicity, pKa and others. In such a context, 1,2- and 1,3-trifluoromethylated alkylamines have attracted a huge interest over the years. However, targeting direct and more sustainable accesses towards these scaffolds, use of transition metals and hardly accessible and expensive fluorine reagents have to be avoided. Moreover, when using environmentally friendly and economical processes, the depicted methods are limited to the formation of amides, sulfonimides or azides. Therefore, this project aims at developing innovative direct and sustainable accesses towards 1,2- and 1,3-polyfluorinated alkylamines including a trifluoromethyl moiety as well as emerging fluorine groups ( -SCF3, -CF2H and -SCF2H). To do so, we are considering to activate commercially available or readily accessible substrates by the use of sustainable energies, which are electricity and visible-light. Redox processes (electrosynthesis and photoredox catalysis) would allow the formation of highly reactive open-shell intermediates to obtain efficiently the desired products in a one-step synthesis.