Li Yuqi, Peng Rongbin, Zhu Chuanle
School of Chemistry and Chemical Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510640, China.
Guangdong Provincial Key Laboratory of Technique and Equipment for Macromolecular Advanced Manufacturing, South China University of Technology, Guangzhou 510640, China.
Org Lett. 2024 Oct 4;26(39):8295-8300. doi: 10.1021/acs.orglett.4c02988. Epub 2024 Sep 23.
A straightforward and efficient strategy for the construction of tertiary and secondary α-aryl acrylamido carboxylic acids is reported. This N-acrylation protocol of unprotected amino acids is achieved by triple C-F bond cleavage of (trifluoromethyl)alkenes. This method features mild conditions, is operationally simple, is free of transition metals and racemization, can be used on a gram scale, and is compatible with various functional moieties. Mechanistic studies indicate that oxygen atom exchange happens among HO, NaOH, and amino acids, and the oxygen atom of the amide moiety of the product is incorporated by the -defluorooxylation of (trifluoromethyl)alkene.
报道了一种构建叔和仲α-芳基丙烯酰胺基羧酸的直接有效策略。这种未保护氨基酸的N-酰化方案是通过（三氟甲基）烯烃的三氟碳-氟键断裂实现的。该方法具有条件温和、操作简单、无过渡金属且无消旋化、可用于克级规模且与各种官能团兼容的特点。机理研究表明，氧原子在HO、NaOH和氨基酸之间发生交换，产物酰胺部分的氧原子通过（三氟甲基）烯烃的脱氟氧合作用引入。
