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

Rajesh Paul, Md Ashif Ali, Tharmalingam Punniyamurthy*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India, Email:

R. Paul, M. A. Ali, T. Punniyamurthy, Synthesis, 2010, 4268-4272.

DOI: 10.1055/s-0030-1258965

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For a selective hydroxylation of aryl iodides and aryl bromides with tetrabutylammonium hydroxide pentahydrate, a combination of copper(I) iodide and 8-hydroxyquinaldine in a mixture of dimethyl sulfoxide and water is used. The resulting phenols can be readily reacted with alkyl and allyl halides in situ to provide the corresponding alkyl or allyl aryl ethers in high yields.

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Key Words

phenols, aryl ethers, copper iodide, tetrabutylammonium hydroxide pentahydrate, aryl halides, hydroxylation

ID: J66-Y2010-3550