Tetrahedron

Electrophilic and nucleophilic side chain fluorination of para-substituted acetophenones

E Fuglseth, THK Thvedt, MF Møll, BH Hoff

Index: Fuglseth, Erik; Thvedt, Thor Hakon Krane; Moll, Maria Forde; Hoff, Bard Helge Tetrahedron, 2008 , vol. 64, # 30-31 p. 7318 - 7323

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Citation Number: 31

Abstract

para-Substituted α-fluoroacetophenones have been synthesised by three different routes. Electrophilic fluorination of trimethylsilyl enol ethers of acetophenones using Selectfluor (F– TEDA–BF4, 1-chloromethyl-4-fluoro-1, 4-diazoniabicyclo [2.2. 2] octane bis- (tetrafluoroborate)) gave high to moderate yield depending on the electronic properties of the substituents. F–TEDA–BF4 mediated fluorination of acetophenones in methanol ...