Truce-smiles rearrangement mediated by ligand-to-iron charge transfer

In this study, we utilized earth-abundant, inexpensive iron as a catalyst and inexpensive, abundant, readily available polyfluoroalkyl carboxylic acids as substrates for sulfone-group-retaining Truce-Smiles rearrangement reactions that were mediated by ligand-to-iron charge transfer. The high oxidation potential of the fluoroalkyl carboxylic acids was overcome by using the iron catalyst; and sulfur dioxide release, which occurs in traditional Truce-Smiles rearrangement reactions, was avoided by adding water to the reaction mixture. Using this mild, operationally simple method, we synthesized a series of polyfluoroalkylated aromatic sulfones, amines, and alcohols from heteroaromatic hydrocarbons and electrophiles. We utilized earth-abundant, inexpensive iron as a catalyst and inexpensive, abundant, readily available polyfluoroalkyl carboxylic acids as substrates for sulfone-group-retaining Truce-Smiles rearrangement reactions that were mediated by ligand-to-iron charge transfer.