A General and Mild Ullmann-Type Synthesis of Diaryl Ethers

Henri-Jean Cristau,* Pascal P. Cellier, Samy Hamada, Jean-Francis Spindler,† and Marc Taillefer*;
Laboratoire de Chimie Organique (CNRS UMR 5076), Ecole Nationale Suprieure de Chimie de Montpellier, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France
Org. Lett., 2004, 6 (6), pp 913–916
DOI: 10.1021/ol036290g
Publication Date (Web): February 20, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Current address:  RHODIA Organique Fine, Centre de Recherches de Lyon (CRL), 85 avenue des Frères Perret, BP 62, 69192 Saint-Fons Cedex, France.

, cristau@cit.enscm.fr, ; , taillefe@cit.enscm.fr

Abstract

Abstract Image

An efficient method for the synthesis of diaryl ethers under particularly mild conditions is described. Inexpensive ligands were found to greatly accelerate the Ullmann-type coupling of aryl bromides or iodides with phenols. A series of diaryl ethers were obtained with excellent yields in acetonitrile in the presence of Cs2CO3 and catalytic copper(I) oxide. The reaction tolerates substrates with unfavorable substitution patterns, such as sterically hindered coupling partners or electron-rich aryl halides.

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History

  • Published In Issue March 18, 2004
  • Received November 24, 2003

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