2-Cyanochromone (1) readily undergoes visible light-induced photocycloadditions with diverse alkene partners mediated by (Ir[dF(CF)ppy](dtbpy))PF as the photosensitizer. While mono-, di- and trisubstituted styrenes and acrylonitriles as the reactants lead to [2 + 2] cycloadducts with good regiocontrol and high diastereoselectivity, the use of trialkyl-substituted alkenes allows for the isolation of cyclopentenone-fused chromones resulting from a [3 + 2] cycloaddition process in moderate yields.
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