The single electron reduction of a carbon-halogen bond is an important transformation in organic synthesis. This process can be employed to initiate hydrodehalogenations of organic halides as well as the inter- or intramolecular addition of carbon-centered radicals to radicophiles. These reductions are traditionally performed through the addition of a stoichiometric electron transfer agent which can be expensive, toxic, or difficult to separate from products. Photoredox catalysis represents a significant advancement in reduction of carbon-halogen bonds under mild conditions and the irradiation of visible light. This poster will present the catalytic mechanism of a visible light-mediated radical arylation by an alkyl bromide determined through kinetic, synthetic, and spectroscopic analysis, as well as a method for the reductive hydrodehalogenation of alkyl, aryl, and alkenyl bromides.

Visible light-mediated single electron reductions of carbon halogen bonds: Mechanistic properties and method development

248th National Meeting (2014)

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