Microwave assisted fluorofunctionalization of phenyl substituted alkenes using selectfluor

• Published in: Journal of fluorine chemistry 2013-06, Vol.150, p.72-77
• Main Authors: Kumar, Anil, Singh, Tej Vir, Venugopalan, Paloth
• Format: Article
• Language: English
• Subjects: Alkenes; Fluorofunctionalization; Fluorohydrins; Microwave; Selectfluor™ (F-TEDA-BF4)
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2013.02.014

A 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. [Display omitted] ► 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. 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.