Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3989-3996.DOI: 10.6023/cjoc202304013 Previous Articles     Next Articles

Mn(acac)3促进烯醇酯与亚磷酸酯的自由基氧化偶联反应合成β-酮膦酸酯

霍炳豪*(), 郭聪慧, 徐占辉*()   

  1. 郑州大学化学学院 绿色催化中心 郑州 450001
  • 收稿日期:2023-04-10 修回日期:2023-06-05 发布日期:2023-06-26
  • 基金资助:
    河南省高校科技创新人才(2021-CX-018)

Mn(acac)3 Promoted Radical Oxidative Coupling Reaction of Enol Esters with Phosphites to Synthesize β-Ketophosphonates

Binghao Huo(), Conghui Guo, Zhanhui Xu()   

  1. Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001
  • Received:2023-04-10 Revised:2023-06-05 Published:2023-06-26
  • Contact: E-mail: huobh668@sina.com; zhxu@zzu.edu.cn
  • Supported by:
    Program for Science & Technology Innovation Talents in Universities of Henan Province(2021-CX-018)

β-Ketophosphonates are widely found in the structural backbone of natural products and biologically active molecules, and they are of great synthetic value in medicinal chemistry, organic transformations and other fields. An Mn(acac)3-promoted oxidative coupling reaction between aryl enol acetates and alkyl phosphites are reported, enabling the synthesis of β-ketophosphonates with broad functional group compatibility under mild and simple conditions. The generation of phosphorus radicals for manganese oxidation and the addition of radicals to unsaturated bonds were involved in the reaction. The substrates required for the reaction were readily available and the system did not require any acid or base as additives. Finally, a gram-scale experiment to further demonstrate the value of this strategy in the efficient synthesis of β-ketophospho- nates was carried out.

Key words: β-ketophosphonates, radical addition, oxidative coupling