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Catalytic intramolecular aminoarylation of unactivated alkenes with aryl sulfonamides.

ABSTRACT: Arylethylamines are abundant motifs in myriad natural products and pharmaceuticals, so efficient methods to synthesize them are valuable in drug discovery. In this work, we disclose an intramolecular alkene aminoarylation cascade that exploits the electrophilicity of a nitrogen-centered radical to form a C-N bond, then repurposes the nitrogen atom's sulfonyl activating group as a traceless linker to form a subsequent C-C bond. This photoredox catalysis protocol enables the preparation of densely substituted arylethylamines from commercially abundant aryl sulfonamides and unactivated alkenes under mild conditions. Reaction optimization, scope, mechanism, and synthetic applications are discussed.

SUBMITTER: Noten EA

PROVIDER: S-EPMC9200115 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Catalytic intramolecular aminoarylation of unactivated alkenes with aryl sulfonamides.

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

Chemical science 20220511 23

Arylethylamines are abundant motifs in myriad natural products and pharmaceuticals, so efficient methods to synthesize them are valuable in drug discovery. In this work, we disclose an intramolecular alkene aminoarylation cascade that exploits the electrophilicity of a nitrogen-centered radical to form a C-N bond, then repurposes the nitrogen atom's sulfonyl activating group as a traceless linker to form a subsequent C-C bond. This photoredox catalysis protocol enables the preparation of densely ...[more]

PMID: 35774166

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