Photochemical C3-amination of pyridines via Zincke imine intermediates

Kitti Franciska Szabó, Piotr Banachowicz, Antoni Powała, Danijela Lunic, Ignacio Funes Ardoiz () and Dorota Gryko ()
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Kitti Franciska Szabó: Institute of Organic Chemistry Polish Academy of Sciences
Piotr Banachowicz: Institute of Organic Chemistry Polish Academy of Sciences
Antoni Powała: Institute of Organic Chemistry Polish Academy of Sciences
Danijela Lunic: Universidad de La Rioja
Ignacio Funes Ardoiz: Universidad de La Rioja
Dorota Gryko: Institute of Organic Chemistry Polish Academy of Sciences

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: 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.

Date: 2025
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DOI: 10.1038/s41467-025-59809-9

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