Recent Progress in Diaryl Ether Synthesis

Rok Frlan; Danijel Kikelj

doi:10.1055/s-2006-942440

REVIEW

Recent Progress in Diaryl Ether Synthesis

Rok Frlan, Danijel Kikelj*
University of Ljubljana, Faculty of Pharmacy, Aškerčeva 7, 1000 Ljubljana, Slovenia
Fax: +386(1)4258031; e-Mail: danijel.kikelj@ffa.uni-lj.si;

Abstract

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Abstract

Diaryl ethers form an important class of organic compounds, both in life sciences and in the polymer industry. In general, diaryl ethers can be synthesized by means of copper-catalyzed Ullmann diaryl ether coupling, palladium-catalysed Buchwald-Hartwig reaction, nucleophilic aromatic substitution, arylboronic acid diaryl ether coupling, oxidative coupling, and nucleophilic aromatic addition to metal-arene complexes. This review covers the progress in diaryl ether synthesis since 1999, with literature coverage through September 2005.

1 Introduction
2 Ullmann and Buchwald-Hartwig Diaryl Ether Coupling Reactions
2.1 Intermolecular Ullmann Diaryl Ether Coupling Reactions
2.2 Intermolecular Palladium-Catalyzed Diaryl Ether Coupling Reactions
2.3 Intramolecular Palladium- and Copper-Mediated Diaryl Ether Coupling Reactions
3 Synthesis of Diaryl Ethers via Nucleophilic Aromatic Substitution
3.1 Intermolecular Nucleophilic Aromatic Substitution
3.2 Intramolecular Nucleophilic Aromatic Substitution
4 Coupling of Phenols with Arylboronic Acids
4.1 Intermolecular Coupling of Phenols with Arylboronic Acids
4.2 Intramolecular Coupling of Phenols with Arylboronic Acids
5 Diaryl Ether Synthesis via Benzyne Mechanism
6 S_nAr Additions to Metal-Arene Complexes
6.1 Intermolecular S_nAr Additions to Metal-Arene Complexes
6.2 Intramolecular S_nAr Additions to Metal-Arene Complexes
7 Diaryl Ether Synthesis via Oxidative Coupling
8 Diaryl Ether Synthesis by Fischer Chromium Carbene Mediated Benzannulation
9 Summary

Key words

diaryl ether - Ullmann reaction - coupling reactions - Buchwald-Hartwig reaction - arylboronic acids

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