A novel improvement in ArLPdF catalytic fluorination of aromatic compounds

In this study, we used reverse micellar medium for overcoming the disadvantages of ArLMF catalytic fluorination of aromatic compounds. It not only enhanced the fluorination rate, but also widened the scope of reaction for bromoaromatics with electron donating and withdrawing functionalities at ortho position. Various bromoaromatic compounds were fluorinated using the biarylphosphine ligand i.e. cyclohexyl BrettPhos ligand, along with [cinnamylPdCl]2, and CsF as the fluoride source in reverse micellar media. The anisotropic palisade layer of reverse micelles provided the active site for reaction. The most crucial factor in the critical reductive elimination step could be the spatial orientation of ArLPdF complex in the palisade layer; forming ArF as the final product in high yield with excellent selectivity.

Reverse micellar media was used to overcome the drawbacks of ArLMF catalytic fluorination of aromatic compounds, which not only enhanced the fluorination rate but also widened the scope of reaction for the bromoaromatics with electron donating and withdrawing functionalities at ortho position.Figure optionsDownload high-quality image (133 K)Download as PowerPoint slideResearch highlights▶ Fluorination of bromoaromatic compounds in reverse micellar media. ▶ Formation of fluoroaromatic compounds in high yield with excellent selectivity. ▶ The reductive elimination of ArLPdF in the anisotropic palisade layer of micelles. ▶ The use of cyclohexyl biarylphosphine ligand without formation of any dimeric product. ▶ Useful catalysis for bromoaromatics with e− withdrawing and donating functionalities.