Photochemical C3-amination of pyridines via Zincke imine intermediates
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Photochemical C3-amination of pyridines via Zincke imine intermediates.pdf (1.6 MB)
0000-0001-6224-1342 Date
2025
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Nature Portfolio
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Abstract
Selective skeletal and peripheral editing of the pyridine moiety has broadly expanded the chemical space. While C-H functionalization at C2 and C4 positions are enabled by the inherent reactivity of this heteroarene, selective derivatization at the C3 position has long posed a significant challenge. Recently, based on a dearomatization-rearomatization sequence, involving Zincke imine intermediates, selective halogenation (-Br, -Cl, and -I) and isotopic labelling were accomplished. Here, we report a mild and regioselective method for C3-amination that relies on the photochemical reaction of Zincke imine with an amidyl radical generated from N-aminopyridinium salts. Mechanistic and theoretical studies indicate that radical intermediates are involved and explain the C3 regioselectivity of the reaction.
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Nat. Commun., 2025, 16, 5072 // https://doi.org/10.1038/s41467-025-59809-9