Copper-Catalyzed Hydroxylation of Aryl Halides with Tetrabutylammonium Hydroxide: Synthesis of Substituted Phenols and Alkyl Aryl Ethers

Abstract

The selective hydroxylation of aryl iodides and aryl bromideswith tetrabutylammonium hydroxide pentahydrate is described. Forthis, the combination of copper(I) iodide and 8-hydroxyquinaldineat 70-130 ˚C in a mixture of dimethylsulfoxide and water (2:3) is used. The resultant phenols can bereadily reacted with alkyl and allyl halides in situ to providethe corresponding alkyl or allyl aryl ethers in high yields. Thereactions are simple, general, and efficient, affording substitutedphenols and alkyl aryl ethers under aerobic conditions.