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<p>Aminoboron compounds are privileged scaffolds in pharmaceutical chemistry, yet general and efficient access to <i>δ</i>-aminoborates remains underdeveloped. Herein, we report a photocatalytic energy transfer (EnT)-enabled radical 1,2-boron migration strategy for the modular assembly of <i>δ</i>-aminoboronate frameworks. Under mild conditions, photoexcitation of readily designed <i>β</i>-boryl oxime esters triggers decarboxylative radical generation and subsequent intramolecular 1,2-boron shift, delivering distal carbon-centered radicals. This platform enables chemo- and regioselective 1,4-difunctionalization of a wide range of unsaturated systems, including alkenes, C=N, and N=N bonds. Remarkably, the strategy is further extended to alkyne–alkene relay systems, enabling direct 1,6-aminoborylation for efficient construction of distal aminoboronic esters. This EnT-based approach overcomes limitations in atom economy and regioselectivity inherent in conventional single-electron-transfer (SET) manifolds. The reaction exhibits broad substrate scope (&gt;70 examples), excellent functional group tolerance, and scalability. Synthetic utility is demonstrated through downstream transformations to access valuable <i>δ</i>-amino alcohols and related pharmacophores, establishing a versatile route to distal aminoboronates with potential applications in synthetic and medicinal chemistry.</p>

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Harnessing energy-transfer catalysis for modular δ-aminoboronate synthesis via radical 1,2-boryl migration

  • 期刊论文

  • 发表日期：

    2026年4月16日

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  • Shan-Shan Li,
  • Yu-Shi Jiang,
  • Dan-Na Chen,
  • Fu-Qin Zhang,
  • Yan Lei,
  • Hai-Tao Tang,
  • Peng-Ju Xia

摘要

Aminoboron compounds are privileged scaffolds in pharmaceutical chemistry, yet general and efficient access to δ-aminoborates remains underdeveloped. Herein, we report a photocatalytic energy transfer (EnT)-enabled radical 1,2-boron migration strategy for the modular assembly of δ-aminoboronate frameworks. Under mild conditions, photoexcitation of readily designed β-boryl oxime esters triggers decarboxylative radical generation and subsequent intramolecular 1,2-boron shift, delivering distal carbon-centered radicals. This platform enables chemo- and regioselective 1,4-difunctionalization of a wide range of unsaturated systems, including alkenes, C=N, and N=N bonds. Remarkably, the strategy is further extended to alkyne–alkene relay systems, enabling direct 1,6-aminoborylation for efficient construction of distal aminoboronic esters. This EnT-based approach overcomes limitations in atom economy and regioselectivity inherent in conventional single-electron-transfer (SET) manifolds. The reaction exhibits broad substrate scope (>70 examples), excellent functional group tolerance, and scalability. Synthetic utility is demonstrated through downstream transformations to access valuable δ-amino alcohols and related pharmacophores, establishing a versatile route to distal aminoboronates with potential applications in synthetic and medicinal chemistry.