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<p>Unactivated alkenes are normally regarded as unfavorable substrates in radical transformations, due to the lack of <i>p-π</i> conjugation that efficiently stabilizes radical intermediates. Functional group migration presents a robust strategy for radical difunctionalization of unactivated alkenes, and has made a great progress over the past few decades. However, the migration of ester group has been relatively less investigated. Herein, we disclose a copper-catalyzed ester group migration to unactivated alkene, applied for 1,2,3-trifunctionalization of allyl benzoates. A variety of <i>α,α</i>-difluoro-<i>γ</i>-hydroxy aliphatic esters are readily obtained.</p>

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Radical-mediated Ester Group Migration for 1,2,3-Trifunctionalization of Allyl Benzoates

  • 期刊论文

  • 发表日期：

    2025年10月22日

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  • Ziqiang Wang,
  • Xin Shao,
  • Yasu Chen,
  • Chen Zhu

摘要

Unactivated alkenes are normally regarded as unfavorable substrates in radical transformations, due to the lack of p-π conjugation that efficiently stabilizes radical intermediates. Functional group migration presents a robust strategy for radical difunctionalization of unactivated alkenes, and has made a great progress over the past few decades. However, the migration of ester group has been relatively less investigated. Herein, we disclose a copper-catalyzed ester group migration to unactivated alkene, applied for 1,2,3-trifunctionalization of allyl benzoates. A variety of α,α-difluoro-γ-hydroxy aliphatic esters are readily obtained.