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<p>Grushin’s reagent, (bpy)Cu(CF<sub>3</sub>)<sub>3</sub>, is a well-known trifluoromethylation agent, but its potential as a difluorocarbene source has remained largely unexplored. Here, we present a photo- and acid-mediated strategy that repurposes Grushin’s reagent as an efficient difluorocarbene precursor for the difluoromethylation of diverse alcohols, including complex primary, secondary, and tertiary alcohols bearing multiple polar functional groups. This method exhibits broad functional group compatibility and has been successfully applied to the late-stage modification of complex natural products and bioactive molecules. A notable achievement is the regioselective difluoromethylation of saccharides and polyols, a challenging transformation enabled by Me<sub>2</sub>SnCl<sub>2</sub>, which serves a dual role as a hydroxyl activator and an in situ source of hydrogen chloride. Antifungal activity evaluation reveals that compounds <b>3c</b> and <b>3n</b> possess good efficacy, highlighting their potential as promising leads for antifungal development.</p>

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Repurposing trifluoromethyl copper (III) complexes for difluoromethylation of saccharides and complex alcohols

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年4月13日

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  • Shuolu Dai,
  • Chuhong Xie,
  • Shan Long,
  • Min Luo,
  • Chen Chen,
  • Tingting Li,
  • Wen-Xin Lv,
  • Yonggui Robin Chi

摘要

Grushin’s reagent, (bpy)Cu(CF3)3, is a well-known trifluoromethylation agent, but its potential as a difluorocarbene source has remained largely unexplored. Here, we present a photo- and acid-mediated strategy that repurposes Grushin’s reagent as an efficient difluorocarbene precursor for the difluoromethylation of diverse alcohols, including complex primary, secondary, and tertiary alcohols bearing multiple polar functional groups. This method exhibits broad functional group compatibility and has been successfully applied to the late-stage modification of complex natural products and bioactive molecules. A notable achievement is the regioselective difluoromethylation of saccharides and polyols, a challenging transformation enabled by Me2SnCl2, which serves a dual role as a hydroxyl activator and an in situ source of hydrogen chloride. Antifungal activity evaluation reveals that compounds 3c and 3n possess good efficacy, highlighting their potential as promising leads for antifungal development.