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Flynn, Autumn R; McDaniel, Kelly A; Hughes, Meredith E; Vogt, David B; Jui, Nathan T
Journal of the American Chemical Society, 05/2020, Letnik: 142, Številka: 20Journal Article
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.
