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<p>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 <i>N</i>-aminopyridinium salts. Mechanistic and theoretical studies indicate that radical intermediates are involved and explain the C3 regioselectivity of the reaction.</p>

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Photochemical C3-amination of pyridines via Zincke imine intermediates

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年5月31日

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  • Kitti Franciska Szabó,
  • Piotr Banachowicz,
  • Antoni Powała,
  • Danijela Lunic,
  • Ignacio Funes Ardoiz,
  • Dorota Gryko

摘要

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.