Monofluoromethyl-Substituted Sulfonium Ylides:Preparation,Structure-Reactivity Study and Substrate Scope  

作　　者：Xin Hong Yafei Liu Long Lu Qilong Shen 

机构地区：[1]Key Laboratory of Orgonofluorine Chemistry,Center for Excellence in Molecular Synthesis,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,345 Lingling Road,Shanghai 200032,China [2]Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,345 Ling ling Road,Shanghai 200032,China

出　　处：《Chinese Journal of Chemistry》2020年第11期1317-1331,共15页中国化学（英文版）

基　　金：The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China(21625206,21632009,21421002);the Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000)for financial support.

摘　　要：of main observation and conclusion Structure-reactivity study of a family of electrophilic monofluoromethylating reagents based on sulfonium ylide skeleton with different steric hindrance and electron-withdrawing properties was described.These studies led us to discover two highly reactive reagents 3 with a cyclic malonate backbone and 6 with an electron-poor 1,1,1,5,5,5-hexafluoropentane-2,4-dione backbone.The high reactivity of reagent 6 allowed to highly selectively access either C-monofluoromethylated or O-monofluoromethylated p-ketoesters in high yields by the use of different bases.In addition,reactions of reagent 3 with a variety of nucleophiles including phenols,carboxylic acids,thiophenols or heteroaryl nucleophiles occurred in full conversion within 10 min at room temperature and the scopes for these reactions were reported in detail.

关 键 词：BACKBONE REAGENT REACTIVITY 

分 类 号：O64[理学—物理化学]