Microwave assisted fluorofunctionalization of phenyl substituted alkenes using selectfluor™

A rapid fluorofunctionalization of alkenes and diene using selectfluor™ has been uncovered. The olefins such as 1-phenyl ethene; 1,1-diphenylethene; (E)-1,2-diphenylethene; (E)-1,2-dinaphthylethene; 1,1,2-triphenylethene; 1,1,2,2-tetraphenylethene and 1,1,4-triphenyl-1,3-butadiene react with selectfluor™ (F-TEDA-BF4) in water and methanol to give α-fluorohydrins and α-fluoromethoxy compounds respectively under microwave radiations. The electrophilic addition of ‘FOH’ and ‘FOMe’ on the double bond occurs regioselectively with excellent yield.

Graphical abstractA rapid fluorofunctionalization of phenyl substituted alkenes using selectfluor™ (F-TEDA-BF4) in water and methanol occurs to give α-fluorohydrins and α-fluoromethoxy compounds respectively under microwave radiations. The electrophilic addition of ‘FOH’ and ‘FOMe’ on the double bond takes place regioselectively with excellent yield.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A rapid fluorofunctionalization of alkenes occurs using selectfluor™ and microwaves. ► Phenyl group plays a crucial role during the fluorofunctionalization of alkenes. ► Addition of ‘FOH’ and ‘FOMe’ takes place regioselectively on alkenes.