Practical synthesis of 3-aryl anthranils via an electrophilic aromatic substitution strategy |
| |
Authors: | Yang Gao Simin Yang Minwei She Jianhong Nie Yanping Huo Qian Chen Xianwei Li Xiao-Qiang Hu |
| |
Institution: | 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 |
| |
Abstract: | 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 Tf2O 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.A practical route for the synthesis of valuable 3-aryl anthranils from readily available anthranils and simple arenes has been achieved through an electrophilic substitution and rearomatization sequence by employing Tf2O as an effective activator. |
| |
Keywords: | |
|
|