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<p>Palladium-catalyzed switchable <i>β</i>-carbon elimination to extrude norbornene for selective synthesis of different heterocyclic skeletons is a long-standing challenge. Herein, we describe the switchable chemoselective synthesis of biologically active C4-carbamoylated indoles and C10-aminophenanthridinones by controlling <i>β</i>-carbon elimination, using chlorocarbamates as C–H carbamoylation reagents. Among them, C4-carbamoylated indoles are used for the synthesis of <i>M2 receptor antagonists</i> and <i>p38α inhibitors</i>. Mechanistic studies show that when <i>β</i>-carbon elimination is inhibited, the catalytic cycle goes through C–N bond coupling and <i>retro</i>-Diels-Alder reaction to generate C4-carbamoylated indoles. Alternatively, when <i>β</i>-carbon elimination to extrude norbornene occurs, an intramolecular C–H arylation cyclization reaction generates C10-aminophenanthridinones.</p><p></p>

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Palladium-catalyzed selective assembly of carbamoylated indoles and aminophenanthridinones via β-carbon elimination switch

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年11月17日

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  • Bo-Sheng Zhang,
  • Yi-Ming Wang,
  • Jun-Shi Zhou,
  • Xin-Yue Fu,
  • Sven Trienes,
  • Tian-Jiao Guo,
  • Xue-Ya Gou,
  • Xi-Cun Wang,
  • Zheng-Jun Quan,
  • Lutz Ackermann,
  • Yong-Min Liang

摘要

Palladium-catalyzed switchable β-carbon elimination to extrude norbornene for selective synthesis of different heterocyclic skeletons is a long-standing challenge. Herein, we describe the switchable chemoselective synthesis of biologically active C4-carbamoylated indoles and C10-aminophenanthridinones by controlling β-carbon elimination, using chlorocarbamates as C–H carbamoylation reagents. Among them, C4-carbamoylated indoles are used for the synthesis of M2 receptor antagonists and p38α inhibitors. Mechanistic studies show that when β-carbon elimination is inhibited, the catalytic cycle goes through C–N bond coupling and retro-Diels-Alder reaction to generate C4-carbamoylated indoles. Alternatively, when β-carbon elimination to extrude norbornene occurs, an intramolecular C–H arylation cyclization reaction generates C10-aminophenanthridinones.