Iodine-Catalyzed Tandem Oxidative Aromatization For The Synthesis Of Meta-Substituted Alkoxybenzenes

A rapid method for the synthesis of meta-substituted alkoxybenzenes is achieved by oxidation of cyclohexenones. This one-pot transformation is catalyzed by molecular iodine with DDQ as an oxidant in the presence of alcohols. Diverse cyclohexenones with aryl or alkyl substitutes are well tolerated to the mild oxidative conditions affording desired products in up to 92% yield. These oxidizing processes were applicable to the efficient synthesis of useful meta-substituted phenolic products which are difficult to obtain by traditional electrophilic substitutions. (C) 2021 Elsevier Ltd. All rights reserved.