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<p>Herein, we describe a strategy for constructing pyrroles via a copper-catalyzed [4 + 1] annulation of yne-allylic esters and aliphatic amines. The key innovation of this approach is the development of copper-ammonium intermediates that facilitate selective C–N bond cleavage under mild conditions. This method demonstrates broad applicability, accommodating both aliphatic secondary amines and aliphatic primary amines, while exhibiting excellent tolerance toward a wide range of functional groups. Furthermore, the ease of subsequent transformations underscores its potential utility in the synthesis of bioactive compounds. Preliminary mechanistic investigations suggest the involvement of a copper-ammonium species, providing insight into the reaction’s underlying process.</p>

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Copper-catalyzed Larock-type cyclization/debenzylation of yne-allylic esters with aliphatic amines

  • 期刊论文

  • 发表日期：

    2025年1月20日

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  • Rongkang Huang,
  • Yuepeng Lu,
  • Feng Xu,
  • Jianhang Huang,
  • Cuiju Zhu,
  • Hao Xu

摘要

Herein, we describe a strategy for constructing pyrroles via a copper-catalyzed [4 + 1] annulation of yne-allylic esters and aliphatic amines. The key innovation of this approach is the development of copper-ammonium intermediates that facilitate selective C–N bond cleavage under mild conditions. This method demonstrates broad applicability, accommodating both aliphatic secondary amines and aliphatic primary amines, while exhibiting excellent tolerance toward a wide range of functional groups. Furthermore, the ease of subsequent transformations underscores its potential utility in the synthesis of bioactive compounds. Preliminary mechanistic investigations suggest the involvement of a copper-ammonium species, providing insight into the reaction’s underlying process.