Arene dearomatization through a catalytic N-centered radical cascade reaction

Rory C. McAtee, Efrey A. Noten and Corey R. J. Stephenson ()
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Rory C. McAtee: University of Michigan
Efrey A. Noten: University of Michigan
Corey R. J. Stephenson: University of Michigan

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Arene dearomatization reactions are an important class of synthetic technologies for the rapid assembly of unique chemical architectures. Herein, we report a catalytic protocol to initiate a carboamination/dearomatization cascade that proceeds through transient sulfonamidyl radical intermediates formed from native sulfonamide N–H bonds leading to 1,4-cyclohexadiene-fused sultams. Importantly, this work demonstrates a facile approach to employ two-dimensional aromatic compounds as modular building blocks to generate richly substituted, three-dimensional compounds. These reactions occur at room temperature under visible light irradiation and are catalyzed by the combination of an iridium(III) photocatalyst and a dialkyl phosphate base. Reaction optimization, substrate scope, mechanistic features, and synthetic applications of this transformation are presented.

Date: 2020
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DOI: 10.1038/s41467-020-16369-4

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