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DOI: https://doi.org/10.6023/cjoc202505033

研究论文

室温下PPh3催化环丙烯酮与溴代烷烃的开环加成反应合成α, β-二取代丙烯酸酯

  • 徐程 ,
  • 彭涛 ,
  • 周梦圆 ,
  • 刘明琳 ,
  • 黄晓庆 ,
  • 王永凤 ,
  • 刘郑 ,
  • 殷国栋
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  • 湖北师范大学化学化工学院 污染物分析与资源化湖北省重点实验室 湖北黄石 435002

收稿日期: 2025-05-29

  修回日期: 2025-07-29

  网络出版日期: 2025-08-27

基金资助

国家自然科学基金(No. 22301071)、湖北省中央引导地方科技发展专项(No. 2024CSA097)、湖北省自然科学基金(Nos. 2023AFB459, 2023AFB477)、大学生创新创业训练计划(Nos. 202410513026, S202410513063) 资助项目.

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Synthesis of α, β-Disubstituted Acrylates via PPh3-catalyzed Ring-opening Addition Reaction of Cyclopropenones with Alkyl Bromides at Room Temperature

  • Xu Cheng ,
  • Peng Tao ,
  • Zhou Mengyuan ,
  • Liu Minglin ,
  • Huang Xiaoqing ,
  • Wang Yongfeng ,
  • Liu Zheng ,
  • Yin Guodong
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  • Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, Hubei 435002

Received date: 2025-05-29

  Revised date: 2025-07-29

  Online published: 2025-08-27

Supported by

National Natural Science Foundation of China (No. 22301071), the Special Fund Project for Guiding Local Science and Technology Development of Hubei Province by the Central Government (No. 2024CSA097), the Natural Science Foundation of Hubei Province (Nos. 2023AFB459, 2023AFB477) and the College Students' Innovation and Entrepreneurship Training Program (Nos. 202410513026, S202410513063).

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摘要

成功开发了一种PPh3催化环丙烯酮与卤代烷的开环加成反应,为室温下合成具有E型立体选择性的α, β-二取代丙烯酸酯提供了一种简洁实用的方法。机理研究表明,α, β-不饱和丙烯酸酯中乙烯基上的氢原子和酯基中的一个氧原子均源自反应溶剂DMSO中所含的水。此外,通过开展克级规模实验及产物的衍生化修饰,进一步拓展了该方法在有机合成中的应用潜力。

关键词： 环丙烯酮; 膦催化; α, β-二取代丙烯酸酯; 开环加成反应

本文引用格式

徐程 , 彭涛 , 周梦圆 , 刘明琳 , 黄晓庆 , 王永凤 , 刘郑 , 殷国栋 . 室温下PPh3催化环丙烯酮与溴代烷烃的开环加成反应合成α, β-二取代丙烯酸酯[J]. 有机化学, 0 : 8 -8 . DOI: 10.6023/cjoc202505033

Abstract

A PPh3-catalyzed ring-opening addition reaction of cyclopropenones with alkyl bromides has been successfully established. This reaction offers a concise and practical approach for the assembly of α, β-disubstituted acrylates with exclusive E-stereoselectivity at room temperature. Mechanistic investigations indicated that both the hydrogen atom on vinyl group and one oxygen atom on ester group of α, β-disubstituted acrylates derive from H₂O in solvent DMSO. Furthermore, a gram-scale experiment and late-stage modification of the products were accomplished, thereby expanding the application potential of this methodology in organic synthesis.

Key words： cyclopropenones; phosphine-catalyzed; α, β-unsaturated acrylates; ring-opening addition reaction

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