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Catalytic Intramolecular Aminoarylation of Unactivated Alkenes with Aryl Sulfonamides
preprintsubmitted 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.
Photochemical synthesis of bioactive molecules
National Institute of General Medical SciencesFind out more...