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<p>Cycloolefin is a privileged motif with significant implications across multiple disciplines. While cycloolefination represents the most unified disconnection strategy, the corresponding approaches are notably scarce. Here we report a hydrazine-mediated carbonyl–alkyne reductive olefination (CARO), offering a minimalist approach to structurally complex cycloolefins. This CARO protocol is also applicable to carbonyl–allene and lactol–alkyne analogues. Experimental studies and DFT calculations suggest that the CARO follows a domino mechanism involving carbonyl–hydrazine condensation, ene reaction of free hydrazone, and denitrogenative retro-ene reaction. Its synthetic potential is demonstrated by the facile preparation of several medicinally important molecules, deuterated compounds and valuable chirons. This study provides a fundamentally distinct, operationally simple and cost-effective strategy for accessing complex architectures, appealing to both organic and medicinal chemists.</p>

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Hydrazine-mediated carbonyl–alkyne/allene reductive olefination

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年5月22日

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  • Linjun Qi,
  • Wencan Wang,
  • Lijin Zhou,
  • Zhi-Xiang Yu,
  • Xiaofeng Tong

摘要

Cycloolefin is a privileged motif with significant implications across multiple disciplines. While cycloolefination represents the most unified disconnection strategy, the corresponding approaches are notably scarce. Here we report a hydrazine-mediated carbonyl–alkyne reductive olefination (CARO), offering a minimalist approach to structurally complex cycloolefins. This CARO protocol is also applicable to carbonyl–allene and lactol–alkyne analogues. Experimental studies and DFT calculations suggest that the CARO follows a domino mechanism involving carbonyl–hydrazine condensation, ene reaction of free hydrazone, and denitrogenative retro-ene reaction. Its synthetic potential is demonstrated by the facile preparation of several medicinally important molecules, deuterated compounds and valuable chirons. This study provides a fundamentally distinct, operationally simple and cost-effective strategy for accessing complex architectures, appealing to both organic and medicinal chemists.