Synthesis of Aryl Ethers from Aromatic Carboxylic Acids

Sukalyan Bhadra; Wojciech I. Dzik; Lukas J. Gooßen

doi:10.1055/s-0033-1339470

Synthesis, Table of Contents

Synthesis 2013; 45(17): 2387-2390
DOI: 10.1055/s-0033-1339470

practical synthetic procedures

Synthesis of Aryl Ethers from Aromatic Carboxylic Acids

Sukalyan Bhadra

Department of Chemistry, Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany Fax: +49(631)2053921 Email: goossen@chemie.uni-kl.de

,

Wojciech I. Dzik

Department of Chemistry, Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany Fax: +49(631)2053921 Email: goossen@chemie.uni-kl.de

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Lukas J. Gooßen*

Department of Chemistry, Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany Fax: +49(631)2053921 Email: goossen@chemie.uni-kl.de

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Abstract

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Abstract

A silver/copper bimetallic catalyst system promotes the decarboxylative Chan–Evans–Lam alkoxylation of ortho-substituted aromatic carboxylate salts with tetraalkyl orthosilicates or triaryl borates. Non-ortho-substituted carboxylates are alkoxylated via an ortho-C–H-alkoxylation with concomitant cleavage of the carboxylate directing group via protodecarboxylation. This way, meta-substituted carboxylates are converted into para-substituted alkoxyarenes and vice versa. The combined processes provide a convenient synthetic entry to the important class of aromatic ethers from widely available carboxylic acids.

Key words

aryl ethers - C–C activation - C–H activation - C–O bond formation - decarboxylative coupling

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References

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