Gao Yang, Yang Simin, She Minwei, Nie Jianhong, Huo Yanping, Chen Qian, Li Xianwei, Hu Xiao-Qiang
School of Chemical Engineering and Light Industry, Guangdong University of Technology Guangzhou 510006 China
Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central University for Nationalities Wuhan 430074 China.
Chem Sci. 2022 Jan 27;13(7):2105-2114. doi: 10.1039/d1sc06565c. eCollection 2022 Feb 16.
We report a practical route for the synthesis of valuable 3-aryl anthranils from readily available anthranils and simple arenes by using the classical electrophilic aromatic substitution (EAS) strategy. This transformation goes through an electrophilic substitution and rearomatisation sequence by employing TfO as an effective activator. A wide range of arenes were compatible in this transformation, delivering various structurally diversified 3-aryl anthranils in good yields and high regioselectivity. In addition, a variety of readily available feedstocks such as olefins, alkenyl triflates, silyl enolethers, carbonyl compounds, thiophenols and thiols could also participate in the reaction to achieve the C3 alkenylation, alkylation and thioetherification of anthranils. Of note, the synthesized 3-aryl anthranils proved to be a highly robust platform to access a series of biologically active compounds, drug derivatives and organic optoelectronic materials.
我们报道了一种实用的合成路线，通过经典的亲电芳香取代（EAS）策略，从容易获得的邻氨基苯甲酸和简单芳烃合成有价值的3-芳基邻氨基苯甲酰胺。这种转化通过使用TfO作为有效的活化剂，经历亲电取代和再芳构化序列。多种芳烃在这种转化中具有兼容性，以良好的产率和高区域选择性提供各种结构多样的3-芳基邻氨基苯甲酰胺。此外，各种容易获得的原料，如烯烃、烯基三氟甲磺酸酯、硅烯醇醚、羰基化合物、苯硫酚和硫醇，也可以参与反应，实现邻氨基苯甲酰胺的C3烯基化、烷基化和硫醚化。值得注意的是，合成的3-芳基邻氨基苯甲酰胺被证明是一个高度稳健的平台，可用于获得一系列生物活性化合物、药物衍生物和有机光电材料。
