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<p>Epoxides are ubiquitous synthetic building blocks owing to the numerous tactics for their C–O bond cleavage. Remarkably, epoxides also undergo selective C–C bond cleavage by a broad range of transformations, utilizing orthogonal conditions to override the conventional C–O bond scission. These strategies allow the construction of diverse oxygenated cyclic and acyclic molecular backbones, often challenging to access otherwise. Here, we discuss the various modes of epoxide C–C bond cleavage reactions, highlighting synthetic applications of these reactions and suggesting directions for the further development of these powerful, yet underutilized, methods.</p><p></p>

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Methods and applications for epoxide C–C bond cleavage reactions

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • Noam Orbach,
  • Zachary P. Sercel,
  • Rahul Suresh,
  • Ilan Marek

摘要

Epoxides are ubiquitous synthetic building blocks owing to the numerous tactics for their C–O bond cleavage. Remarkably, epoxides also undergo selective C–C bond cleavage by a broad range of transformations, utilizing orthogonal conditions to override the conventional C–O bond scission. These strategies allow the construction of diverse oxygenated cyclic and acyclic molecular backbones, often challenging to access otherwise. Here, we discuss the various modes of epoxide C–C bond cleavage reactions, highlighting synthetic applications of these reactions and suggesting directions for the further development of these powerful, yet underutilized, methods.