Late-stage introduction of alkyl and perfluoroalkylated groups onto unfunctionalized positions on a drug scaffold holds significant potential utility in medicinal chemistry applications. Traditional methods for the Minisci decarboxylation of carboxylic acids typically require high temperatures, as well as silver and persulfate reagents as oxidants. Herein we report a redox-neutral method for the decarboxylative alkylation of heterocyclic N-oxides using photoredox catalysis. This protocol induces decarboxylation through single-electron reduction, a concept which may help to improve the functional group tolerance and overall chemoselectivity of this transformation. Moreover, this method features the use of simple, commercially available carboxylic acid derivatives as alkylating agents, enabling the facile alkylation of a variety of biologically-relevant heterocyclic scaffolds under mild conditions.

Decarboxylative alkylation of biologically relevant heterocycles using photoredox catalysis

253rd National Meeting (2017)

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