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<p>Skeletal editing has emerged as a powerful strategy for organic synthesis, addressing a long-standing synthetic challenge between molecular scaffolds. In recent years, skeletal editing (insertion, deletion, and swap) undergoes rapid evolution and realizes many remarkable transformations between basic or complex molecular skeletons. Different from atom insertion and deletion reactions, atom swap reactions enable selective exchange of atoms in a single step. Among existing atom swap strategies, the editing of aromatic scaffolds has been extensively studied, while the editing of aliphatic scaffolds remains limited to only a few reports. Tetrahydrofuran rings, as one of the most common aliphatic scaffolds, are highly attractive targets for conversion into high-value pyrrolidines. Herein, we report a practical and straightforward method to convert tetrahydrofurans to <i>N</i>-acyl pyrrolidines using nitriles as the nitrogen source, achieving oxygen-to-nitrogen (O-to-N) atom swap in one step.</p>

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Skeletal editing of tetrahydrofurans to pyrrolidines through O-to-N single atom swap

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2026年4月11日

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  • Shihan Geng,
  • Tieqiao Wang,
  • Qingxuan Kong,
  • Dunhang Ouyang,
  • Changwei Jiang,
  • Ning Jiao,
  • Song Song

摘要

Skeletal editing has emerged as a powerful strategy for organic synthesis, addressing a long-standing synthetic challenge between molecular scaffolds. In recent years, skeletal editing (insertion, deletion, and swap) undergoes rapid evolution and realizes many remarkable transformations between basic or complex molecular skeletons. Different from atom insertion and deletion reactions, atom swap reactions enable selective exchange of atoms in a single step. Among existing atom swap strategies, the editing of aromatic scaffolds has been extensively studied, while the editing of aliphatic scaffolds remains limited to only a few reports. Tetrahydrofuran rings, as one of the most common aliphatic scaffolds, are highly attractive targets for conversion into high-value pyrrolidines. Herein, we report a practical and straightforward method to convert tetrahydrofurans to N-acyl pyrrolidines using nitriles as the nitrogen source, achieving oxygen-to-nitrogen (O-to-N) atom swap in one step.