Catalytic intramolecular aminoarylation of unactivated alkenes with aryl sulfonamides |
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Authors: | Efrey A Noten Rory C McAtee Corey R J Stephenson |
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Institution: | University of Michigan, Department of Chemistry, Willard Henry Dow Laboratory, 930 North University Ave., Ann Arbor MI 48109 USA, |
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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.A photochemical assembly of cyclic arylethylamines occurs by cascade radical annulation and desulfonylative rearrangement in N-acyl sulfonamides. This aminoarylation is made possible through judicious design intended to thwart undesired reactivity. |
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