<br/>The generation of radical anion intermediates has enabled numerous valuable transformations over the past century. These methods have traditionally relied upon strong stoichiometric reductants (e.g. Na/NH<sub>3</sub>) which preclude the interception of transient radical intermediates. In this presentation, we report the generation of aryl and heteroaryl radical anions under mild photocatalytic conditions. Following heterolytic cleavage of a suitable halide, we demonstrate regioselective addition to a wide variety of alkene and alkyne subtypes. This concept has been applied towards the synthesis of alkylated pyridine species via heteroaryl radicals, in addition to fluorogenic molecules via intermediate difluorobenzylic radicals.

Radical anions as reactive intermediates for the synthesis of complex molecules

2019 Fall National Meeting

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