Phosphonium ionic liquids as highly thermal stable and efficient phase transfer catalysts for solid–liquid Halex reactions

Trihexyl (tetradecyl) phosphonium tetrafluoroborate was found to be an active catalyst for the introduction of fluoride by nucleophilic aromatic substitution. With a decomposition temperature above 300 °C, this ionic liquid is suitable for reactions at high temperatures. The addition of 1 mol% of the ionic liquid relative to KF increased the initial rate for the fluorination of 1,2-dichloro-4-nitrobenzene six-fold compared to the uncatalysed reaction. The highest reaction rate was observed at 20 mol% ionic liquid relative to KF. Ease of handling without the need for stringent drying conditions and reuseability make this ionic liquid a useful phase transfer catalyst.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (188 K)Download as PowerPoint slideHighlights► Trihexyl (tetradecyl) phosphonium tetrafluoroborate as an active phase transfer catalyst in Halex reactions using KF. ► Reaction rate increased even at low loadings. ► Reactions can be carried out at high temperatures due to high thermal stability. ► Green system due to ease of reuse with minimal loss of activity.