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<p>Functional group displacement and migration represent powerful, yet underexplored strategies in synthetic chemistry, offering unique opportunities for molecular diversification and drug discovery. Here, we report a nickel-catalyzed deoxygenative trifunctionalization of vinyl triflates, which enables the efficient synthesis of structurally diverse, boron-containing polysubstituted cyclohexanes featuring quaternary carbon centers. This reaction is a key step enabling aryl displacement of a ketone group and its migration to an adjacent carbon center. Notably, the transformation exhibits broad substrate scope and exceptional, programmable diastereoselectivity in arylative ketone migration. Moreover, this transformation enables efficient <i>α</i>-arylation of unsymmetrical ketones with excellent regio- and diastereoselective control—an outcome that remains challenging to achieve using existing methods. Furthermore, this strategy is particularly well-suited for the late-stage functionalization of structurally complex bioactive molecules, facilitating the rapid generation of analogs.</p>

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Ketone displacement and migration enabled by trifunctionalization of vinyl triflates

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年2月27日

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  • Shiyang Wang,
  • Tong Yao,
  • Yu Liu,
  • Yangyang Li,
  • Guoyin Yin

摘要

Functional group displacement and migration represent powerful, yet underexplored strategies in synthetic chemistry, offering unique opportunities for molecular diversification and drug discovery. Here, we report a nickel-catalyzed deoxygenative trifunctionalization of vinyl triflates, which enables the efficient synthesis of structurally diverse, boron-containing polysubstituted cyclohexanes featuring quaternary carbon centers. This reaction is a key step enabling aryl displacement of a ketone group and its migration to an adjacent carbon center. Notably, the transformation exhibits broad substrate scope and exceptional, programmable diastereoselectivity in arylative ketone migration. Moreover, this transformation enables efficient α-arylation of unsymmetrical ketones with excellent regio- and diastereoselective control—an outcome that remains challenging to achieve using existing methods. Furthermore, this strategy is particularly well-suited for the late-stage functionalization of structurally complex bioactive molecules, facilitating the rapid generation of analogs.