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Structure-reactivity study of a family of electrophilic monofluoromethylating reagents based on sul-fonium 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 β-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 nucleo-philes occurred in full conversion within 10 min at room temperature and the scopes for these reactions were reported in detail.