Ketyl Radicals by Photoredox-Catalysed Oxidation of Redox Active Aldehyde Derivatives

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Synthetic utilization of aldehydes is of pivotal importance in organic chemistry. Besides the polar reactivity of aldehydes as electrophiles, ketyl radicals generated by single electron reduction of aldehydes are nucleophilic, therefore offering umpolung reactivity. Traditionally, ketyl radicals are formed under relatively harsh conditions with an excess of strong reductants, limiting their application to reactions which are net reductive. Accessing ketyl radicals by a mechanistically distinct single electron oxidation of aldehyde derivatives can enable net redox-neural transformations. However, existing synthetic strategies to generate ketyl radicals via single-electron oxidation remain rare. In this project, a novel approach will be investigated to afford ketyl radicals under mild conditions via photoredox-catalysed oxidation of aldehyde derivatives. It is hoped that this methodology will be of broad interest in areas such as synthetic and medicinal chemistry.