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2023 , Vol. 43 >Issue 6: 2110 - 2119

DOI: https://doi.org/10.6023/cjoc202208010

研究论文

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
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  • 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

  网络出版日期: 2023-01-12

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)

收起

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
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  • College of Materials and Chemical Engineering, Chuzhou University, Chuzhou, Anhui 239000
* E-mail:

Received date: 2022-08-08

  Revised date: 2022-11-01

  Online published: 2023-01-12

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)

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摘要

报道了铜催化氟代丙烯酸与N-甲苯磺酰氧杂吖丙啶的脱羧偶联反应. 一系列含多种官能团的氟代丙烯酸均是兼容的反应底物. 一级、二级以及三级烷基取代的吖丙啶杂环都可以顺利地参与反应, 以中等以上的收率给出期望的单氟烯烃. 该脱羧反应展现出良好的官能团兼容性及卓越的立体选择性, 为在医药科学和材料科学上有着重要应用价值的单氟烯烃提供了一种新颖、实用的合成策略. 除了α-氟代肉桂酸, β-氟代肉桂酸也可以作为反应底物. 该方法可为多种取代类型的单氟烯烃提供合成途径, 该反应也为活性分子的后期修饰提供了策略.

关键词： 氟代丙烯酸; 吖丙啶; 铜催化; 单氟烯烃; 脱羧

本文引用格式

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 . 铜催化氟代丙烯酸与氧杂吖丙啶的脱羧交叉偶联反应[J]. 有机化学, 2023 , 43(6) : 2110 -2119 . DOI: 10.6023/cjoc202208010

Abstract

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

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