Recent advances in catalytic oxidative reactions of phenols and naphthalenols

Abstract

Oxidative reactions provide an effective strategy for phenol transformation via conjugated addition, C–H functionalization, cyclization reactions, etc. It has enabled broad utilization of phenolic substrates as versatile chemical feedstocks in the preparation of various oxygenated molecules valuable for pharmaceutics, agricultural chemicals, materials, and so on. Many of the reactions are accomplished via quinone intermediates. Despite being versatile synthons in organic synthesis, quinones have to be generally pre-synthesized using stoichiometric metal oxides and stabilized by electron-withdrawing groups to circumvent dimerization or degradation. Their structural diversity, sustainable accessibility, and synthetic potential remain to be further exploited. This review aims at giving an overview of oxidative phenol transformations in nature and synthetic chemistry, including reactions involving the generation of quinone intermediates, oxidative coupling for biaryl formation, and oxidative cyclization into various heterocycles. It offers clear, concise, and illustrated guidelines for synthetic chemists seeking inspiration through catalytic oxidative reactions.