Electrochemical generation of oxygen and nitrogen centred radicals

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The need to design libraries of compounds is essential across a wide diversity of fields such as drug design, new material development or environmental chemistry. Radical chemistry is a unique tool for achieving this goal, via the construction of complex molecular scaffolds under mild conditions, due to the broad array of radical transformation available. Yet one of the major issues remains the generation of those radicals, which very often require the use of toxic metals or unstable and hazardous compounds. For instance, such conditions are incompatible with pharmaceutical applications, where the product has to be produced safely on a large scale and without any trace of toxic contaminant.Electrosynthesis is a powerful tool in organic chemistry that circumvents the afore-mentioned issues by allowing the generation of radicals under mild and green conditions. Even though a plethora of transformations have been developed and many of them have been successfully used in several industrial processes, the potential of preparative organic electrochemistry remains largely underestimated. The growing impetus to look for greener and cheaper alternatives to classic synthetic methodologies has further prompted us to investigate new electrochemical methodologies. Based on very encouraging preliminary results, we envision using electrochemistry to develop a novel way to generate aroyloxy/acryloyl (RCOO*) and amidyl radicals (R2N*) under mild, green, economical and safe conditions. The project proposed is interdisciplinary since, besides the extensive organic synthetic studies, a comprehensive electroanalytical study using high-speed voltammetry will be performed in order to study the electrode mechanisms and establish the mechanism of the reaction.Finally, as a proof of concept, the newly developed synthetic methodologies will be used to generate libraries of bioactive compounds (phthalides, isochromanones, isoindolinones, etc. ). This will lay the ground for future medicinal chemistry grant proposals.Through this research, we will work in close collaboration with IKA which recently released "Electrasyn 2.0", the first commercial electrosynthesis setup. This proposal will lead to constructive feedback that will be shared with IKA in order to develop new applications for Electrasyn 2.0. to further aid research in this area.