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<p>In recent years, amination of alkylboronates through ionic copper catalysis or boron-ate complex 1,2-metalation has been well established, but complementary radical processes remain less studied before. Herein, based on rational design, we develop several imine-type <i>N</i>-centered radical scavengers and apply them to&#xa0;the radical amination of alkylboronates. The reaction proceeds under mild photoredox-catalyzed transition-metal-free conditions and features excellent functional group tolerance. It also enables the preparation of a range of medicinally valuable amine derivatives from complex natural products. Further application of this reagent in C-H amination, deoxygenative amination, decarboxylative amination and three component trifluoromethylative/sulfonylative aminations are also realized. Further mechanistic studies and DFT calculations are conducted to provide detailed evidence for the mechanism.</p>

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Development of N-centered radical scavengers that enables photoredox-catalyzed transition-metal-free radical amination of alkyl pinacol boronates

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年4月4日

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  • Changlei Zhu,
  • Jiaxin Lin,
  • Xiaoguang Bao,
  • Jingjing Wu

摘要

In recent years, amination of alkylboronates through ionic copper catalysis or boron-ate complex 1,2-metalation has been well established, but complementary radical processes remain less studied before. Herein, based on rational design, we develop several imine-type N-centered radical scavengers and apply them to the radical amination of alkylboronates. The reaction proceeds under mild photoredox-catalyzed transition-metal-free conditions and features excellent functional group tolerance. It also enables the preparation of a range of medicinally valuable amine derivatives from complex natural products. Further application of this reagent in C-H amination, deoxygenative amination, decarboxylative amination and three component trifluoromethylative/sulfonylative aminations are also realized. Further mechanistic studies and DFT calculations are conducted to provide detailed evidence for the mechanism.