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Catalytic Intramolecular Aminoarylation of Unactivated Alkenes with Aryl Sulfonamides

preprint
submitted on 26.04.2021, 17:27 and posted on 28.04.2021, 05:30 by Efrey Noten, Rory McAtee, Corey Stephenson
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 under mild conditions. Reaction optimization, scope, mechanism, and synthetic applications are discussed.

Funding

Photochemical synthesis of bioactive molecules

National Institute of General Medical Sciences

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History

Email Address of Submitting Author

crjsteph@umich.edu

Institution

University of Michigan

Country

USA

ORCID For Submitting Author

0000-0002-2443-5514

Declaration of Conflict of Interest

None

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