Catalytic Intramolecular Aminoarylation of Unactivated Alkenes with Aryl Sulfonamides

28 April 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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.


Photoredox Catalysis
Smiles Rearrangements
Radical Cyclization


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