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Arene Dearomatization via Radical Hydroarylation

preprint
submitted on 18.09.2019 and posted on 23.09.2019 by Autumn Flynn, Kelly McDaniel, Meredith Hughes, David Vogt, Nathan Jui
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.

Funding

Targeting the orphan nuclear receptor LRH-1 with small molecules

National Institute of Diabetes and Digestive and Kidney Diseases

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Novel Radical Reactions for C-C Bond Formation

National Institute of General Medical Sciences

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History

Email Address of Submitting Author

autumn.flynn@emory.edu

Institution

Emory University

Country

United States

ORCID For Submitting Author

0000-0003-2504-2365

Declaration of Conflict of Interest

No competing financial interests are declared

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