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Arene dearomatization through a catalytic N-centered radical cascade reaction.

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.

SUBMITTER: McAtee RC

PROVIDER: S-EPMC7239915 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Arene dearomatization through a catalytic N-centered radical cascade reaction.

McAtee Rory C RC Noten Efrey A EA Stephenson Corey R J CRJ

Nature communications 20200520 1

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 buildin ...[more]

PMID: 32433521

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