Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes

What is it about?

A new iron-catalyzed reaction for the coupling of perfluoroalkyl iodides (RFI) with aromatic substrates is described. The perfluoroalkylated arene products are obtained in good to excellent yields in the presence of a [(bpy)Fe(II)] catalyst(10%) electrochemically regenerated or generated from [(bpy)Fe(III)] at room temperature. The development, scope, and preliminary mechanistic studies of these transformations are reported.

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Why is it important?

Perfluoroalkylation of aromatic and hetero-aromatic compounds by C6F13I catalyzed by [(bpy)FeCl3] or [(bpy)FeCl2] under electrochemical conditions was investigated. Fluoroalkylation of benzene derivatives, naphthalene, and caffeine was obtained under mild reaction conditions with high product yields. The mechanism of electrochemical transformation was proposed to be a radical process based on ESR and CV studies.