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<p>The skeletal remodelling of benzene has been widely acknowledged as an attractive yet challenging approach for utilizing the extensive array of aromatic compounds. A primary challenge lies not only in overcoming the high activation barrier associated with the dearomatization step but also in achieving site-selective skeletal modifications within a single operational sequence. Here we present a photothermal cascade activation mode that unlocks the photoactivation reactivity of the transiently generated light-absorbing intermediate formed during interrupted Fischer indolization. Complementary to arene ring expansion methodologies, this protocol offers a practical ring contraction approach for the modular synthesis of fused pyridines with good functional group tolerance and predictable regioselectivity. This strategy is expected to broaden the chemical landscape for the design of innovative photochemical reactions.</p><p></p>

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Photoinduced benzene ring contraction of arylhydrazines for the synthesis of fused pyridines

  • 期刊论文

  • 发表日期：

    2026年1月30日

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  • Kun Li,
  • Yin Zeng,
  • Kai-Hang Li,
  • Yifan Yang,
  • Jinhui Shen,
  • Huifeng Guo,
  • Yingfei Tan,
  • Jing-Jing Guo,
  • Anhua Hu

摘要

The skeletal remodelling of benzene has been widely acknowledged as an attractive yet challenging approach for utilizing the extensive array of aromatic compounds. A primary challenge lies not only in overcoming the high activation barrier associated with the dearomatization step but also in achieving site-selective skeletal modifications within a single operational sequence. Here we present a photothermal cascade activation mode that unlocks the photoactivation reactivity of the transiently generated light-absorbing intermediate formed during interrupted Fischer indolization. Complementary to arene ring expansion methodologies, this protocol offers a practical ring contraction approach for the modular synthesis of fused pyridines with good functional group tolerance and predictable regioselectivity. This strategy is expected to broaden the chemical landscape for the design of innovative photochemical reactions.