Practical Synthesis of NFSI Derivatives through ArSO_(2) NHF without F_(2)  

作　　者：Yu-Yang Zhang Xiu-Hua Xu Feng-Ling Qing 

机构地区：[1]Key Laboratory of Organofluorine Chemistry,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Science,Chinese Academy of Sciences,345 Lingling Lu,Shanghai,200032 China

出　　处：《Chinese Journal of Chemistry》2022年第24期2956-2962,共7页中国化学（英文版）

基　　金：The National Natural Science Foundation of China(21991211);the National Key Research and Development Program of China(2021YFF0701700)are greatly acknowledged for funding this work.

摘　　要：N-Fluorobenzenesulfonimide (NFSI) is one of the most popular fluorine-containing reagents for fluorination, imidation, sulfonylation, and oxidation reactions. Consequently, a variety of NFSI derivatives were designed and synthesized to modify the reactivity and/or selectivity of the parent reagent. However, the hazardous F_(2) was inevitably required for the synthesis of NFSI derivatives. Herein, we disclosed a practical synthesis of various NFSI derivatives without F_(2) in common organic chemistry laboratories. This synthetic protocol started from NFSI through pyridine-promoted desulfonylation for formation of N-fluoroarenesulfonamide (ArSO_(2)NHF) and followed by condensation with arenesulfonyl chlorides. The reduction potentials and fluorinating reactivities of these NFSI derivatives demonstrated that NFSI derivatives bearing the electron-withdrawing groups on benzene ring had the higher oxidizing and fluorinating abilities than NFSI.

关 键 词：FLUORINE Fluorinating reagent SULFONAMIDES Synthetic methods DESULFONYLATION NFSI CONDENSATION 

分 类 号：O62[理学—有机化学]