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<p>Cycloaddition reactions are central to building cyclic molecular architectures for drug discovery and materials science. However, controlling single-atom-bridged cycloaddition remains elusive. Herein, we describe a selenium-atom transfer [3 + 2 + 1] heterocycloaddition of readily available arylamines, alkenes and diselenides, enabling rapid, modular access to diverse selenium- and nitrogen-containing heterocycles, including selenomorpholines and polycyclic 1,4-selenazinanes. This metal-free method operates under mild, simple conditions with scalability, showcasing broad substrate generality and functional group tolerance, is amenable to scalable synthesis, and demonstrates utility in the late-stage skeletal diversification of complex molecules. Mechanistic and computational studies reveal a <i>Se</i>-bridged cycloaddition pathway involving alkene aminoselenylation, followed by electrophilic selenocyclization and deprotonative rearomatization. This heteroatom-driven annulation opens opportunities for the development of reactions for the construction of multi-heteroatom cyclic scaffolds and broader application in selenium-based medicinal chemistry.</p>

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Selenium atom transfer enables selective bridged alkene-arylamine cycloaddition

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2026年7月8日

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  • Jiefeng Hu,
  • Kun Zhang,
  • Jiahao Zhang,
  • Daojing Li,
  • Yongkai Su,
  • Shuangru Chen,
  • Qinqi He,
  • Die Deng,
  • Jing Zhang,
  • Guoqiang Wang,
  • Su Jing

摘要

Cycloaddition reactions are central to building cyclic molecular architectures for drug discovery and materials science. However, controlling single-atom-bridged cycloaddition remains elusive. Herein, we describe a selenium-atom transfer [3 + 2 + 1] heterocycloaddition of readily available arylamines, alkenes and diselenides, enabling rapid, modular access to diverse selenium- and nitrogen-containing heterocycles, including selenomorpholines and polycyclic 1,4-selenazinanes. This metal-free method operates under mild, simple conditions with scalability, showcasing broad substrate generality and functional group tolerance, is amenable to scalable synthesis, and demonstrates utility in the late-stage skeletal diversification of complex molecules. Mechanistic and computational studies reveal a Se-bridged cycloaddition pathway involving alkene aminoselenylation, followed by electrophilic selenocyclization and deprotonative rearomatization. This heteroatom-driven annulation opens opportunities for the development of reactions for the construction of multi-heteroatom cyclic scaffolds and broader application in selenium-based medicinal chemistry.