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<p><i>γ</i>-Hydroxy acid has widespread applications in materials, pharmaceuticals, food industries and organic synthesis. In this context, the CO<sub>2</sub>-involved multi-component reaction of the C-C unsaturated bond represents one of the most promising strategies for preparing <i>γ</i>-hydroxy acids from readily available feedstocks in one step. However, current reports mainly rely on the utilization of limited-access reagents and even stoichiometric metal catalysts, which suppress their application. Herein, we describe a novel example of <i>γ</i>-hydroxy acids enabled by photocatalyzed carboxylative alkylation of styrenes with easy-access aliphatic aldehydes and CO<sub>2</sub>. This protocol offers a facile tool to furnish a variety of <i>γ</i>-hydroxy acids with good functional group compatibility and can be further applied to the late-stage modification of biomolecules, as well as ligation of drug fragments. The developed reaction can be seamlessly scaled up using flow technology, rendering its practicality. Additionally, this platform enables the downstream synthesis of furan-2(5<i>H</i>)-one <b>67</b>, which shows attractive anti-cancer efficacy against a set of tumor cells, further highlighting the significance of our protocol.</p>

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Modular assembly of aldehydes, styrenes and CO2 for the synthesis of γ-hydroxy acids under organophotocatalysis

  • 期刊论文

  • 发表日期：

    2025年7月7日

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  • Zeyou Wang,
  • Ziye Wei,
  • Shouhui Liu,
  • Chenxuan Xu,
  • Xijuan Yao,
  • Lifei Han,
  • Xiujuan Feng,
  • Ming Bao,
  • Weili Si,
  • Xuan Zhang

摘要

γ-Hydroxy acid has widespread applications in materials, pharmaceuticals, food industries and organic synthesis. In this context, the CO2-involved multi-component reaction of the C-C unsaturated bond represents one of the most promising strategies for preparing γ-hydroxy acids from readily available feedstocks in one step. However, current reports mainly rely on the utilization of limited-access reagents and even stoichiometric metal catalysts, which suppress their application. Herein, we describe a novel example of γ-hydroxy acids enabled by photocatalyzed carboxylative alkylation of styrenes with easy-access aliphatic aldehydes and CO2. This protocol offers a facile tool to furnish a variety of γ-hydroxy acids with good functional group compatibility and can be further applied to the late-stage modification of biomolecules, as well as ligation of drug fragments. The developed reaction can be seamlessly scaled up using flow technology, rendering its practicality. Additionally, this platform enables the downstream synthesis of furan-2(5H)-one 67, which shows attractive anti-cancer efficacy against a set of tumor cells, further highlighting the significance of our protocol.