George Shia

1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) as a new, effective reagent for selective fluorofunctionalisation of alkenes under mild reaction conditions

Abstract 1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) ( Accufluor ™ NFTh) is confirmed as a highly effective reagent for introducing a fluorine atom into organic molecules across a phenyl-substituted carbon-carbon double bond. Quantitative and Markovnikov-type regioselective formation of vicinal fluoro-hydroxy, fluoro-methoxy or fluoro-acetoxy adducts was achieved when phenyl-substituted alkenes were treated with a MeCN solution of NFTh In the presence of water, methanol or acetic acid. The stereochemical course of fluoro-methoxylation reactions in the case of cyclic phenyl-substituted alkenes depends strongly on the structure of the alkene.

1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate): An electrophilic fluorinating agent

Abstract 1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), NFTh, is a electrophilic fluorinating that can be used to fluorinate aromatic rings, olefins, dienol acetates and enol ethers. When NFTh is reacted with an active methylene compound in the presence of ZnCl 2 , the corresponding monoor di-fluoro derivative can be isolated.

γ-Fluorination of unsaturated ketones with N-fluorobenzenesulfonimide

Abstract The reaction of potassium dienoxy borates with N-fluorobenzenesulfonimide affords γ-fluoro enones in good yields. The potassium dienoxy borates are prepared by treating potassium enolates derived from unsaturated ketones with 2-phenyl-1,3,2-benzodiosaborole.