铜催化氟代丙烯酸与氧杂吖丙啶的脱羧交叉偶联反应  

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

作　　者：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 Lu Xiaoyu;Sun Xiaomei;Niu Yaqing;Wang Junchao;Yin Wenjing;Gao Mengting;Liu Zi;Wei Zhenghuan;Tao Tinghua(College of Materials and Chemical Engineering,Chuzhou University,Chuzhou,Anhui 239000)

机构地区：[1]滁州学院材料与化学工程学院,安徽滁州239000

出　　处：《有机化学》2023年第6期2110-2119,共10页Chinese Journal of Organic Chemistry

基　　金：国家自然青年科学基金(No.22001029);安徽省青年科学基金(No.2008085QB92);安徽省高等学校自然科学重点研究(No.KJ2020A0708)资助项目。

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.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.

关 键 词：氟代丙烯酸 吖丙啶 铜催化 单氟烯烃 脱羧 

分 类 号：O621.251[理学—有机化学]