Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 1977-1984.DOI: 10.6023/cjoc201805027 Previous Articles     Next Articles



王华斌a,b, 付强c, 张智杰c,d, 高明a,b, 姬建新a, 易东c   

  1. a 中国科学院成都生物研究所 成都 610041;
    b 中国科学院大学 北京 100049;
    c 西南医科大学药学院 泸州 646000;
    d 西南医科大学药物研究中心 泸州 646000
  • 收稿日期:2018-05-11 修回日期:2018-05-30 发布日期:2018-06-01
  • 通讯作者: 易东
  • 基金资助:


Hydrochloric Acid-Promoted Copper/Iron-Cocatalyzed Deesterifica-tive Oxyphosphorylation of 2-Substituted Acrylates with H-Phosphine Oxides

Wang Huabina,b, Fu Qiangc, Zhang Zhijiec,d, Gao Minga,b, Ji Jianxina, Yi Dongc   

  1. a Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041;
    b University of the Chinese Academy of Sciences, Beijing 100049;
    c School of Pharmacy, Southwest Medical University, Luzhou 646000;
    d Drug Discovery Reseach Center, Southwest Medical University, Luzhou 646000
  • Received:2018-05-11 Revised:2018-05-30 Published:2018-06-01
  • Contact: 10.6023/cjoc201805027
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21572217), the Strategic Biological Resources Service Network Program of Chinese Academy of Sciences (No. ZSTH-001) and the Scientific Research Foundation of Southwest Medical University (No. 2017-ZRZD-020).

An unprecedented method for the transformation of 2-substituted acrylates into β-ketophosphine oxides has successfully been developed via hydrochloric acid-promoted copper/iron-cocatalyzed deesterificative oxyphosphorylation under dioxygen atmosphere, simultaneously inhibiting the formation of the preceding hydroxyphosphorylation products. Through this convenient and practical process, a library of structurally diverse β-ketophosphine oxides could be selectively and effectively obtained with broad substrate scope and good functional group tolerance under mild conditions, accompanied by chemoselective cleavage of C(sp2)-C(C=O) bonds.

Key words: β-ketophosphine oxides, 2-substituted acrylates, hydrochloric acid, copper/iron-cocatalysis, dioxygen