Facile Preparation of Unsymmetrical Diaryl Ethers from Unsymmetrical Diaryliodonium Tosylates and Phenols with High Regioselectivity

Yohji Kakinuma; Katsuhiko Moriyama; Hideo Togo

doi:10.1055/s-0032-1316824

Synthesis, Table of Contents

Synthesis 2013; 45(2): 183-188
DOI: 10.1055/s-0032-1316824

paper

Facile Preparation of Unsymmetrical Diaryl Ethers from Unsymmetrical Diaryliodonium Tosylates and Phenols with High Regioselectivity

Yohji Kakinuma

Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan Fax: +81(43)2902792 Email: togo@faculty.chiba-u.jp

,

Katsuhiko Moriyama

Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan Fax: +81(43)2902792 Email: togo@faculty.chiba-u.jp

,

Hideo Togo*

Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan Fax: +81(43)2902792 Email: togo@faculty.chiba-u.jp

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Abstract

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Abstract

Unsymmetrical diaryl ethers were efficiently obtained in good yields by the reactions of aryl(4-methoxyphenyl)iodonium tosylates with phenols, and aryl(2,4-dimethoxyphenyl)iodonium tosylates with phenols, in the presence of potassium carbonate in acetonitrile, respectively. The latter iodonium tosylates provided the corresponding unsymmetrical diaryl ethers in good yields with high regioselectivities, together with the quantitative formation of 1-iodo-2,4-dimethoxybenzene.

Key words

unsymmetrical diaryliodonium tosylate - unsymmetrical diaryl ether - aryl(4-methoxyphenyl)iodonium tosylate - aryl(2,4-dimethoxyphenyl)iodonium tosylate

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References

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