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Synthesis 2012; 44(10): 1551-1555
DOI: 10.1055/s-0031-1290966
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Regioselective C–H Aerobic Oxidative Cycloetherification of o-Arylphenols Bearing an Additional Directing Group

Jiaji Zhao
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, P. R. of China, Fax: +86(20)32015321   eMail: zhu_qiang@gibh.ac.cn
,
Yong Wang
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, P. R. of China, Fax: +86(20)32015321   eMail: zhu_qiang@gibh.ac.cn
,
Qiang Zhu*
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, P. R. of China, Fax: +86(20)32015321   eMail: zhu_qiang@gibh.ac.cn
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Publikationsverlauf

Received: 26. März 2012

Accepted: 30. März 2012

Publikationsdatum:
23. April 2012 (online)

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Abstract

An efficient copper-catalyzed C–H oxidative cycloetherification of o-arylphenols containing an additional directing group under an oxygen atmosphere was developed. 2,6-Disubstituted dibenzofuran derivatives were prepared by regioselective activation of the sterically more hindered C–H bond. The presence of the extra directing group not only controls the regioselectivity, but also increases the cyclization efficiency significantly.

Key words

chelation - copper catalysis - cycloetherification - dibenzofuran - oxidative annulation

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

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