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Synfacts 2011(11): 1238-1238  
DOI: 10.1055/s-0031-1289197
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Trifluoromethylation of Aromatic Isoxazoles

Contributor(s): Paul Knochel, Thomas Kunz
H. Kawai, K. Tachi, E. Tokunaga, M. Shiro, N. Shibata*
Nagoya Institute of Technology and Rigaku Corporation, Tokyo, Japan
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

In this work a trifluoromethylation of substituted aromatic isoxazoles is described. The direct nucleophilic addition to the C5 position is achieved by the presence of an electron-withdrawing nitro group on the adjacent C4 position. This reaction leads to 5-trifluoromethyl-2-isoxazolines with the CF3 substituent on a quaternary carbon center, which is a common structural element of heterocyclic compounds in agro- and medicinal chemistry.