Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2110-2119.DOI: 10.6023/cjoc202208010 Previous Articles     Next Articles

铜催化氟代丙烯酸与氧杂吖丙啶的脱羧交叉偶联反应

陆晓雨*(), 孙晓梅, 钮亚琴, 王俊超, 殷文婧, 高梦婷, 刘孜, 韦正桓, 陶庭骅   

  1. 滁州学院材料与化学工程学院 安徽滁州 239000
  • 收稿日期:2022-08-08 修回日期:2022-11-01 发布日期:2023-01-11
  • 基金资助:
    国家自然青年科学基金(22001029); 安徽省青年科学基金(2008085QB92); 安徽省高等学校自然科学重点研究(KJ2020A0708)

Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines

Xiaoyu Lu*(), Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao   

  1. College of Materials and Chemical Engineering, Chuzhou University, Chuzhou, Anhui 239000
  • Received:2022-08-08 Revised:2022-11-01 Published:2023-01-11
  • Contact: E-mail: xiaoyulu@mail.ustc.edu.cn
  • Supported by:
    National Natural Science Foundation of China(22001029); Natural Youth Science Foundation of Anhui Province(2008085QB92); Natural Science Research Key Project of Anhui Higher Education Institution(KJ2020A0708)

A protocol for the copper-catalyzed decarboxylative cross-coupling of α‑fluoroacrylic acids with N-tosyl oxaziridines was reported. A series of substituted α-fluoroacrylic acids, and primary, secondary and tertiary substituted oxaziridines were suitable reaction substrates. The decarboxylation reaction exhibited good functional group compatibility and excellent Z-stereoselectivity. This method provides a novel and practical strategy for the construction of monofluoroalkenes, which are key functional groups in the pharmaceutical and material sciences. In addition to α-fluoroacrylic acids, β- fluoroacrylic acid could also participate in the reaction smoothly, which provides a protocol to access various substituted monofluoroalkenes. This methodology also provides a platform for the modification of complex biologically active molecules.

Key words: fluoroacrylic acids, oxaziridines, copper-catalyzed, monofluoroalkene, decarboxylative