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The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans

Kevin W. Anderson, Takashi Ikawa, Rachel E. Tundel and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

K. W. Anderson, T. Ikawa, R. E. Tundel, S. L. Buchwald, J. Am. Chem. Soc., 2006, 128, 10694-10695.

DOI: 10.1021/ja0639719 (free Supporting Information)


Abstract

The direct and selective palladium-catalyzed synthesis of phenols from aryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts and the biphasic solvent system 1,4-dioxane/H2O. A one-pot method for the preparation of alkyl aryl ethers from aryl halides and the preparation of substituted benzofurans via a Pd-catalyzed phenol formation/cyclization protocol starting from 2-chloroaryl alkynes are described.

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Key Words

Phenols, Arylethers, Etherification, Benzofurans


ID: J48-Y2006-2670