Arene Dearomatization via Radical Hydroarylation

23 September 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 cyclization event, giving rise to 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.

Keywords

dearomatization
radical
hydroarylation
photoredox
spirocycle

Supplementary materials

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Rxiv-Arene Dearomatization-Supporting Information
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