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Issue 25, 2016
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Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C–H arylation

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Abstract

We report conditions for the preparation of a range of trifluoromethylated isoxazole building blocks through the cycloaddition reaction of trifluoromethyl nitrile oxide. It was found that controlling the rate (and therefore concentration) of the formation of the trifluoromethyl nitrile oxide was Critical for the preferential formation of the desired isoxazole products versus the furoxan dimer. Different conditions were optimised for both aryl- and alkyl-substituted alkynes. In addition, the reactivity at the isoxazole 4-position has been briefly explored for these building blocks. Conditions for intermolecular C–H arylation, lithiation and electrophile quench, and alkoxylation were all identified with brief substrate scoping that signifies useful tolerance to a range of functionalities. Finally, complementary processes for structural diversification through either intramolecular cyclisation or intermolecular cross-coupling were developed.

Graphical abstract: Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C–H arylation

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Publication details

The article was received on 04 May 2016, accepted on 20 May 2016 and first published on 20 May 2016


Article type: Paper
DOI: 10.1039/C6OB00970K
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Citation: Org. Biomol. Chem., 2016,14, 5983-5991
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    Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C–H arylation

    J. Poh, C. García-Ruiz, A. Zúñiga, F. Meroni, D. C. Blakemore, D. L. Browne and S. V. Ley, Org. Biomol. Chem., 2016, 14, 5983
    DOI: 10.1039/C6OB00970K

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