Work

Hydroarylation of Arenes via Reductive Radical-Polar Crossover

Year: 2020

Type: article

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 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.0c03926

Authors: Autumn R. Flynn, Kelly A. McDaniel, Meredith E. Hughes, David B. Vogt, Nathan T. Jui

Institutions: Emory University, Winship Cancer Institute

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institute of General Medical Sciences, National Institute of Diabetes and Digestive and Kidney Diseases

Awards: Novel Radical Reactions for C-C Bond Formation, Targeting the orphan nuclear receptor LRH-1 with small molecules, G911242656