Synthesis 2013; 45(2): 183-188
DOI: 10.1055/s-0032-1316824
paper
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 10 October 2012

Accepted after revision: 13 November 2012

Publication Date:
30 November 2012 (online)


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.

 
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