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A Green and Novel Method for the Synthesis of 4,4-Difluoro-3- oxo-2-(triphenylphosphoranylidene) 5-Lactones by Reformatsky Reaction    

A Green and Novel Method for the Synthesis of 4,4-Difluoro-3- oxo-2-(triphenylphosphoranylidene) 5-Lactones by Reformatsky Reaction

文献类型:期刊文献

中文题名:A Green and Novel Method for the Synthesis of 4,4-Difluoro-3- oxo-2-(triphenylphosphoranylidene) 5-Lactones by Reformatsky Reaction

英文题名:A Green and Novel Method for the Synthesis of 4,4-Difluoro-3- oxo-2-(triphenylphosphoranylidene) 5-Lactones by Reformatsky Reaction

作者:赛达力木[1];方向[1];张栋[1];刘璐[1];吴范宏[1,2]

机构:[1]Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China;[2]School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 200235, China

年份:2011

卷号:29

期号:12

起止页码:2713

中文期刊名:Chinese Journal of Chemistry

外文期刊名:中国化学(英文版)

收录:CSTPCD;;Scopus;CSCD:【CSCD2011_2012】;

基金:Project supported by the National Natural Science Foundation of China (NNSFC) (Nos. 20972050, 21172148).

语种:中文

中文关键词:aqueous medium;4-bromo-4,4-difluoro-3-oxo-2-(triphenylphosphoranylidene)butanoate;Reformatsky reaction;indium

外文关键词:aqueous medium, 4-bromo-4,4-difluoro-3-oxo-2-(triphenylphosphoranylidene)butanoate, Reformatsky reaction, indium

摘要:In the presence of In/CuCl, ethyl 4-bromo-4,4-difluoro-3-oxo-2-(triphenylphosphoranylidene)butanoate reacted with various aldehydes in aqueous medium at room temperature to give the a,a-difluorinated β-hydroxy carbonyl compounds. Furthermore, treating Reformatsky addition compounds with 1 equiv, of sodium hydroxide in the mixture of tetrahydrofuran and water afforded gem-difluoromethylenated 2-triphenylphosphoranylidene δ-lactones in excellent yields.
In the presence of In/CuCl, ethyl 4-bromo-4,4-difluoro-3-oxo-2-(triphenylphosphoranylidene)butanoate reacted with various aldehydes in aqueous medium at room temperature to give the a,a-difluorinated β-hydroxy carbonyl compounds. Furthermore, treating Reformatsky addition compounds with 1 equiv, of sodium hydroxide in the mixture of tetrahydrofuran and water afforded gem-difluoromethylenated 2-triphenylphosphoranylidene δ-lactones in excellent yields.

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