Hydroarylation of Arenes via Reductive Radical-Polar Crossover

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 regio...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2020-05, Vol.142 (20), p.9163-9168
Main Authors: Flynn, Autumn R, McDaniel, Kelly A, Hughes, Meredith E, Vogt, David B, Jui, Nathan T
Format: Article
Language:English
Subjects:
Benzene Derivatives - chemistry
Cyclohexenes - chemical synthesis
Cyclohexenes - chemistry
Free Radicals - chemistry
Molecular Structure
Oxidation-Reduction
Photochemical Processes
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c03926