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  • Title: The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.
    Author: Anderson KW, Ikawa T, Tundel RE, Buchwald SL.
    Journal: J Am Chem Soc; 2006 Aug 23; 128(33):10694-5. PubMed ID: 16910660.
    Abstract:
    The direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd(2)dba(3) and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H(2)O. We have also demonstrated a one-pot method of phenol formation/alkylation for the preparation of alkyl aryl ethers from aryl halides. In many instances, this protocol overcomes limitations in existing Pd-catalyzed coupling reactions of aliphatic alcohols with aryl halides. Finally, we demonstrate that substituted benzofurans can be prepared efficiently via a Pd-catalyzed phenol formation/cyclization protocol starting from 2-chloroaryl alkynes.
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