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Hydroarylation of Arenes via Reductive Radical-Polar Crossover.

ABSTRACT: A photocatalytic system for the dearomative hydroarylation of benzene derivatives has been developed. Using a combination of an organic photoredox catalyst and an amine reductant, this process operates through a reductive radical-polar crossover mechanism where aryl halide reduction triggers a regioselective radical cyclization event, followed by anion formation and quenching to produce a range of complex spirocyclic cyclohexadienes. This light-driven protocol functions at room temperature in a green solvent system (aq. MeCN) without the need for precious metal-based catalysts or reagents or the generation of stoichiometric metal byproducts.

SUBMITTER: Flynn AR

PROVIDER: S-EPMC7667579 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Hydroarylation of Arenes via Reductive Radical-Polar Crossover.

Flynn Autumn R AR McDaniel Kelly A KA Hughes Meredith E ME Vogt David B DB Jui Nathan T NT

Journal of the American Chemical Society 20200511 20

A photocatalytic system for the dearomative hydroarylation of benzene derivatives has been developed. Using a combination of an organic photoredox catalyst and an amine reductant, this process operates through a reductive radical-polar crossover mechanism where aryl halide reduction triggers a regioselective radical cyclization event, followed by anion formation and quenching to produce a range of complex spirocyclic cyclohexadienes. This light-driven protocol functions at room temperature in a ...[more]

PMID: 32379445

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