Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3264-3271.DOI: 10.6023/cjoc202103038 Previous Articles     Next Articles



许振丽a, 张宗雪b, 孟晨湘b, 张萧雅b, 许凯b,*(), 刘澜涛b,c, 王涛b, 徐海云b, 毛国梁a,*()   

  1. a 东北石油大学化学化工学院 黑龙江大庆 163318
    b 商丘师范学院化学化工学院 药物绿色合成河南省工程实验室 河南商丘 476000
    c 郑州大学化学与分子工程学院 郑州 450001
  • 收稿日期:2021-03-22 修回日期:2021-04-13 发布日期:2021-05-08
  • 通讯作者: 许凯, 毛国梁
  • 基金资助:
    国家自然科学基金(21572126); 国家自然科学基金(21202095); 河南省技术人员队伍建设(C20150030); 河南省科技创新人才计划(184100510011); 河南省自然科学基金(212300410379); 河南省科技重大专项(192102110222)

Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E-Vinylphosphonates

Zhenli Xua, Zongxue Zhangb, Chenxiang Mengb, Xiaoya Zhangb, Kai Xub(), Lantao Liub,c, Tao Wangb, Haiyun Xub, Guoliang Maoa()   

  1. a College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing, Heilongjiang 163318
    b Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000
    c College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
  • Received:2021-03-22 Revised:2021-04-13 Published:2021-05-08
  • Contact: Kai Xu, Guoliang Mao
  • Supported by:
    National Natural Science Foundation of China(21572126); National Natural Science Foundation of China(21202095); Technicians Troop Construction Projects of Henan Province(C20150030); Program of Science and Technology Innovation Talents of Henan Province(184100510011); Natural Science Foundation of Henan Province(212300410379); Key Scientific and Technological Project of Henan Province(192102110222)

A ligand-free Pd-catalyzed hydrophosphorylation of internal alkynes with diphenyl H-phosphonate in various alcohols for the synthesis of E-vinylphosphonates has been reported. This pratical and versatile three-component reaction involves the syn-addition of diphenyl H-phosphonate towards relatively inactive internal alkynes, as well as the concomitant transesterification of diphenyl H-phosphonate. The remarkable features include high stereoselectivity, wide substrate scope and the absence of additional ligands.

Key words: addition reaction, three-component reaction, vinylphosphonate, palladium, internal alkyne