Issue 21, 2013
From the journal:

Organic & Biomolecular Chemistry

Synthesis of tetrasubstituted benzenesvia rhodium(i)-catalysed ring-opening benzannulation of cyclobutenols with alkynes†‡

Takanori Matsuda*a  and  Norio Miuraa  

* Corresponding authors

a Department of Applied Chemistry, Tokyo University of Science, 1–3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
E-mail: mtd@rs.tus.ac.jp
Fax: +81 3 5261 4631

Abstract

A formal [4 + 2] annulation occurs between 1,3-disubstituted cyclobutenols and internal alkynes in the presence of rhodium(I) catalysts to afford 1,2,3,5-tetrasubstituted benzenes. These benzannulation products are generated through dehydration of the initially formed cyclohexadienols.

Graphical abstract: Synthesis of tetrasubstituted benzenes via rhodium(i)-catalysed ring-opening benzannulation of cyclobutenols with alkynes

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Article information

DOI
https://doi.org/10.1039/C3OB40436F
Article type
Communication
Submitted
01 Mar 2013
Accepted
18 Mar 2013
First published
19 Mar 2013

Org. Biomol. Chem., 2013,11, 3424-3427

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Synthesis of tetrasubstituted benzenes via rhodium(I)-catalysed ring-opening benzannulation of cyclobutenols with alkynes

T. Matsuda and N. Miura, Org. Biomol. Chem., 2013, 11, 3424 DOI: 10.1039/C3OB40436F

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