Issue 48, 2014
From the journal:

Organic & Biomolecular Chemistry

An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran using alkoxybenzocyclobutenone as a reactive platform†

Kenta Asahina,a   Suguru Matsuoka,a   Ryosuke Nakayamaa  and  Toshiyuki Hamura*a  

* Corresponding authors

a Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
E-mail: thamura@kwansei.ac.jp
Fax: (+81) 79-565-7591
Tel: (+81) 79-565-7591

Abstract

An efficient synthetic method of 1,3-bis(arylethynyl)isobenzofurans is developed. Nucleophilic addition of alkynyllithium to benzocyclobutenone and subsequent oxidative ring cleavage of the four-membered ring gave a keto-aldehyde, which, in turn, accepted the second nucleophile to produce isobenzofurans after acid treatment.

Graphical abstract: An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran using alkoxybenzocyclobutenone as a reactive platform

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Article information

DOI
https://doi.org/10.1039/C4OB02012J
Article type
Communication
Submitted
20 Sep 2014
Accepted
10 Oct 2014
First published
10 Oct 2014

Org. Biomol. Chem., 2014,12, 9773-9776

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An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran using alkoxybenzocyclobutenone as a reactive platform

K. Asahina, S. Matsuoka, R. Nakayama and T. Hamura, Org. Biomol. Chem., 2014, 12, 9773 DOI: 10.1039/C4OB02012J

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