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Synthesis 2010(24): 4268-4272
DOI: 10.1055/s-0030-1258965
DOI: 10.1055/s-0030-1258965
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Hydroxylation of Aryl Halides with Tetrabutylammonium Hydroxide: Synthesis of Substituted Phenols and Alkyl Aryl Ethers
Further Information
Received
19 July 2010
Publication Date:
09 November 2010 (online)
Publication History
Publication Date:
09 November 2010 (online)
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Abstract
The selective hydroxylation of aryl iodides and aryl bromides with tetrabutylammonium hydroxide pentahydrate is described. For this, the combination of copper(I) iodide and 8-hydroxyquinaldine at 70-130 ˚C in a mixture of dimethyl sulfoxide and water (2:3) is used. The resultant phenols can be readily reacted with alkyl and allyl halides in situ to provide the corresponding alkyl or allyl aryl ethers in high yields. The reactions are simple, general, and efficient, affording substituted phenols and alkyl aryl ethers under aerobic conditions.
Key words
phenols - copper iodide - tetrabutylammonium hydroxide pentahydrate - aryl halides - hydroxylation
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