2,4,6-trisubstituted pyridinium salts have emerged as versatile radical cross couplings handles. Beyond deaminative processes, these scaffolds have the potential to provide a more standardized and general solution to radical generation than organic halides. Despite their emerging utility, methods for their incorporation continue to rely on a small set of decades old transformations, namely condensation of expensive oxopyrylium salts with amines or forcing nucleophilic substitution on a limited scope of substrates. Recently our laboratory has initiated a program towards developing novel oxidative strategies for pyridinium salt synthesis aimed at expanding the scope of available precursors. This talk will describe our recent efforts towards the synthesis of benzylic 2,4,6-trimethyl collidinium salts via an electrochemical C–H functionalization. The method proceeds via an arene radical cation intermediate and is applicable to a broad scope of electron-rich arenes and alkyl substituents with complete site selectivity for C(sp<sup>3</sup>) over C(sp<sup>2</sup>) amination. This approach is simple, cost-effective and provides a mild strategy for collidinium incorporation without the need for substrate prefunctionalization.

Site-selective syntheis of 2,4,6-trimethyl collidinium salts via electrochemical C–H functionalization

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ACS Fall 2022

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