Gold Catalysis: Proof of Arene Oxides as Intermediates in the Phenol Synthesis

An elusive intermediate in the gold-catalyzed phenol synthesis was elucidated by modifying the energy profile of this process. Thus, the use of a ligand based on 2-hydroxymethylpyridine enabled the first observation of the intermediate arene oxide, which can be enriched to account for up to 80 % of the material in the reaction mixture at room temperature (see scheme).