Oxidative Diamination Using Pyridines as Electrochemically Inert Piperidine Equivalents

Abstract The installation of vicinal functionalities such as 1,2-diamines is of great interest to the synthetic community. Amines that exist within saturated heterocyclic scaffolds are important due to the prevalence of heterocycles in medicinal chemistry. Herein, we report an electrochemical strategy for intramolecular difunctionalization of styrenyl olefins using pyridines as masked piperidine equivalents. This method employs readily accessible electrode material, avoids the need for stoichiometric chemical oxidants, and minimizes the formation of wasteful by-products. The resulting benzylic pyridinium salts are versatile scaffolds for downstream functionalization, giving rise to diverse piperidine derivatives.