School of Materials and Chemical Engineering, Chuzhou University, Chuzhou 239000, China.
School of Chemistry and Chemical Engineering, Anhui University, Hefei 230601, China.
J Org Chem. 2022 Apr 1;87(7):4654-4669. doi: 10.1021/acs.joc.1c03088. Epub 2022 Mar 21.
Herein, a new strategy for the synthesis of monofluoroalkenes via employing α-fluoroacrylic acids and -hydroxyphthalimide (NHPI) redox-active esters as coupling partners has been developed. This decarboxylative reaction enabled the formation of C(sp)-C(sp) bonds to provide a practical and efficient approach for the construction of a variety of monofluoroalkenes, which are key structural motifs in organic chemistry, under mild reaction conditions. The protocol exhibited excellent functional group compatibility and delivered monofluoroalkene products with excellent -stereoselectivity. This work also provides a platform for the modification of complex biologically active molecules containing carboxylic acids.
本文开发了一种通过使用α-氟丙烯酸和-N-羟基邻苯二甲酰亚胺（NHPI）氧化还原活性酯作为偶联试剂合成单氟烯烃的新策略。这种脱羧反应能够形成 C(sp)-C(sp)键，为在温和的反应条件下构建各种单氟烯烃提供了一种实用且高效的方法，单氟烯烃是有机化学中的关键结构基序。该方案表现出优异的官能团兼容性，并提供了具有优异立体选择性的单氟烯烃产物。这项工作还为含有羧酸的复杂生物活性分子的修饰提供了一个平台。
