Regioselective Hypervalent-Iodine(III)-Mediated Dearomatizing Phenylation of Phenols through Direct Ligand Coupling

Authors

  • Aurélie Ozanne-Beaudenon,

    1. Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France, Fax: (+33) 540-00-22-15
    2. Laboratoire de Chimie Organique et Organométallique (CNRS UMR5802), Centre de Recherche en Chimie Moléculaire, Université Bordeaux 1, 351 Cours de la Libération, 33405 Talence Cedex, France.
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  • Stéphane Quideau Dr.

    1. Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France, Fax: (+33) 540-00-22-15
    2. Laboratoire de Chimie Organique et Organométallique (CNRS UMR5802), Centre de Recherche en Chimie Moléculaire, Université Bordeaux 1, 351 Cours de la Libération, 33405 Talence Cedex, France.
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  • We gratefully acknowledge Simafex and the Association Nationale de la Recherche Technique (CIFRE Grant N°301/2002) for their financial support and Aurélie Ozanne-Beaudenon’s graduate research assistantship.

Abstract

original image

Dearomatization: Treatment of phenols and naphthols substituted at the ortho position by a small electron-donating group D with chlorodiphenyl-λ3-iodane leads to their regioselective ortho phenylation to give cyclohexa-2,4-dienone derivatives (see scheme). The mechanism of this reaction involves a nonradical direct coupling of the ligands.

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