Hydroarylation of Arenes via Reductive Radical-Polar Crossover
| Autor: | David B. Vogt, Kelly A. McDaniel, Autumn R. Flynn, Nathan T. Jui, Meredith E. Hughes |
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| Rok vydání: | 2020 |
| Předmět: |
Free Radicals
Aryl halide Cyclohexadienes 010402 general chemistry Photochemistry 01 natural sciences Biochemistry Radical cyclization Article Catalysis Colloid and Surface Chemistry Cyclohexenes Benzene Derivatives Spiro Compounds chemistry.chemical_classification Molecular Structure Chemistry Regioselectivity General Chemistry Photochemical Processes 0104 chemical sciences Reagent Photocatalysis Amine gas treating Oxidation-Reduction |
| Zdroj: | J Am Chem Soc |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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