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Synthesis 2009(13): 2155-2162  
DOI: 10.1055/s-0029-1216800
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Mild Oxidation of Diarylacetylenes to 1,2-Diketones Using Oxone in Trifluoroacetic Acid

Jean-Ho Chua, Yen-Ju Chenb, Ming-Jung Wu*a
a Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan 804, Taiwan
b Faculty of Medicinal and Applied Chemistry, Kaohsiung Medicinal University, Kaohsiung, Taiwan 807, Taiwan
Fax: +886(7)5253909; e-Mail: mijuwu@faculty.nsysu.edu.tw;
Further Information

Publication History

Received 4 February 2009
Publication Date:
12 May 2009 (online)

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Abstract

A variety of 1,2-diaryldiketones were synthesized in 15-90% yields by treatment of diarylacetylenes with Oxone as the oxidant in trifluoroacetic acid. Oxidation of 1-nitro-2-(phenylethynyl)benzene and 2,4′-(ethyne-1,2-diyl)bis(nitrobenzene) furnished 1-benzoylbenzo[c]isoxazol-3(1H)-one and benzo[c]isoxazol-3-yl(4-nitrophenyl)methanone as the major products, respectively.

Key words

diarylalkyne - Oxone - oxidation - 1,2-diketone

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The crystal structures of compound 2o [CCDC 716035] and compound 4 [CCDC 716034] have been deposited at the Cambridge Crystallographic Data Centre. The data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].