ArticleJACS Au2026
Radical/Ylide-Tunable Pyridinium Salt Enables Photo/Thermocatalytic Divergent [3 + 2] Cycloadditions.
Article in JACS Au, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Pyridinium salts are valuable building blocks in synthetic design, yet most derivatives display only one reactive mode. We report an α-carboxyalkylpyridinium salt that functions as a dual mode reagent, acting either as a photoactivated radical precursor or as a thermally generated pyridinium ylide. The salt is readily prepared from amino acid and permits divergent [3 + 2] cycloadditions by simply changing the energy input (visible light versus heat). Two photoinduced electron transfer pathwaysintermolecular (with the photocatalyst) and intramolecular (within the pyridinium salt)generate different radical intermediates, which subsequently undergo distinct reaction sequences, affording the same γ-butyrolactone. Thermal activation induces decarboxylation to pyridinium ylides, allowing access to tetrahydroindolizines via 1,3-dipolar cycloaddition, which subsequently undergo an unprecedented photocatalytic 1,2-phenyl migration to yield fluorescent indolizines.
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