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<p>The radical addition/functional group migration strategy has emerged as a powerful tool for the difunctionalization of unsaturated hydrocarbons, yet the heteroatom-mediated functional group migration remains largely unexplored. Herein, we report an unprecedented radical difunctionalization of alkynes employing oxime esters as bifunctional reagents through a novel C-centered radical addition/N-centered radical translocation sequence. This innovative transformation paradigm enables efficient alkylamination of alkynes under mild photocatalytic redox conditions. Mechanistic investigations reveal a cascade sequence initiated by single-electron transfer from oxime derivatives, proceeding through radical addition, 6-<i>exo</i>-trig cyclization, and subsequent imino group migration.</p>

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Oxime ester as bifunctional reagent for the alkylamination of alkynes via C-centered radical addition and N-centered radical migration

  • 期刊论文

  • 发表日期：

    2025年8月18日

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  • Keyuan Zhang,
  • Min Wang,
  • Qi Jiang,
  • Bowu Dong,
  • Xin-Hua Duan,
  • Le Liu

摘要

The radical addition/functional group migration strategy has emerged as a powerful tool for the difunctionalization of unsaturated hydrocarbons, yet the heteroatom-mediated functional group migration remains largely unexplored. Herein, we report an unprecedented radical difunctionalization of alkynes employing oxime esters as bifunctional reagents through a novel C-centered radical addition/N-centered radical translocation sequence. This innovative transformation paradigm enables efficient alkylamination of alkynes under mild photocatalytic redox conditions. Mechanistic investigations reveal a cascade sequence initiated by single-electron transfer from oxime derivatives, proceeding through radical addition, 6-exo-trig cyclization, and subsequent imino group migration.