Electric-field-controlled highly regioselective thiocyanation of N-containing heterocycles

作     者：Ming Gong Qian Wu Jung Keun Kim Mengmeng Huang Yabo Li Yangjie Wu Jong Seung Kim 

作者机构：Henan Key Laboratory of Chemical Biology and Organic ChemistryKey Laboratory of Applied Chemistry of Henan UniversitiesCollege of ChemistryZhengzhou UniversityZhengzhou 450052China Department of ChemistryKorea UniversitySeoul 02841Korea 

出 版 物：《Science China Chemistry》 (中国科学（化学英文版）)

年 卷 期：2024年第67卷第4期

页      面：1263-1269页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：supported by the National Natural Science Foundation of China(21172200,21302172) the Basic Research Training Project of Zhengzhou University(JC2020053021) supported by the National Research Foundation of Korea(CRI Project No.2018R1A3B1052702 for Jong Seung Kim) 

主　　题：electric fields reaction-axis rule electric double layer C7-thiocyanation C-S bond formation 

摘      要：Achieving highly regioselective synthesis in organic chemistry is challenging due to the uncontrollable orientation between reacting *** electric fields(EEFs)can influence the reactivity and selectivity of the substrate by causing directional ***,scalable and efficient techniques for using EEFs as“smart catalystshave been lacking,hindering their *** this study,we present a novel method for modifying the regioselectivity of quinoxaline-2(1H)-ones by functionalizing their C7-position using the electric double layer(EDL)*** approach led to moderate to good yields of the corresponding C7-thiocyanation *** calculations and control experiments demonstrated that EEFs could reverse the regioselectivity of quinoxaline-2(1H)-ones,allowing the C7-thiocyanation to proceed via a radical reaction ***,the resulting 7-thiocyano-1-methylquinoxaline-2(1H)-ones exhibited promising AIE *** work showcases a promising strategy for achieving highly regioselective functionalization by aligning the electric field with the desired reaction/bond axis.