One-Pot Synthesis of meta-Substituted Phenols via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling and Oxidation

We have developed a two-step synthesis of meta-substituted phenols in one pot, in good to excellent yield. A Pd2+ source is the catalyst for both steps of the synthesis, which includes a cross-coupling reaction between -chlorocyclohexenones with boronic acids, followed by aerobic oxidation of the resulting enone. This method is also suitable for the synthesis of meta- and ortho-disubstituted phenols, which have so far been especially difficult to access using existing synthetic methods. The scope of the reaction was explored by combining different substituted -chlorocyclohexenones with a wide range of different boronic acids and boronate esters using optimized reaction conditions, leading to the synthesis of meta-substituted phenols in moderate to good yields.