Nitromethane-Enabled Fluorination of Styrenes and Arenes  

作　　者：Weijin Wang Tongyu Huo Xinyi Zhao Qixue Qin Yujie Liang Song Song Guosheng Liu Ning Jiao 

机构地区：[1]State Key Laboratory of Natural and Biomimetic Drugs,School of Pharmaceutical Sciences,Peking University,Beijing 100191 [2]State Key Laboratory of Pharmaceutical Biotechnology,Nanjing University,Nanjing 210023,Jiangsu [3]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032

出　　处：《CCS Chemistry》2020年第6期566-575,共10页中国化学会会刊（英文）

基　　金：the National Natural Science Foundation of China(nos.21871011,21602005,21632001,and 21772002);the Drug Innovation Major Project(2018ZX09711-001);the Open Fund of State Key Laboratory of Pharmaceutical Biotechnology,Nanjing University,China(grant no.KF-GN-201906).

摘　　要：The electrophilic fluorination of unsaturated compounds provides a reliable approach to the generation of organofluorides,which are used widely in agrochemicals,pharmaceuticals,and other materials.Numerous active electrophilic fluorine reagents,such as the fluorine molecule(F_(2))or xenon difluoride(XeF_(2)),have been applied in fluorination.However,these reagents suffer from their hazardous,toxic,corrosive,and poor selective properties,and the relatively weak electrophilicity of Selectfluor or N-fluorobenzenesulfonimide(NFSI)usually limits their broad applications.Herein,we disclose nitromethane(MeNO_(2))as an efficient activator of Selectfluor and NFSI,as well as a stabilizer of carbocations.Therefore,the fluoro-azidation,fluoroamination,fluoroesterification of styrenes,and C–H fluorination of(hetero)arenes were well realized just by the facilitation of MeNO_(2).The mild reaction conditions and practicability made our current method a versatile protocol for accessing organofluorides.

关 键 词：fluoroazidation fluoroamination fluoroesterification electrophilic fluorination NITROMETHANE 

分 类 号：O62[理学—有机化学]