Access to 5-fluoroisoxazoles via the Nitrosation of Geminal Bromo-fluoro Arylcyclopropanes
2-Aryl-1-bromo-1-fluorocyclopropanes, Nitrosonium chlorosulfate, 3-Aryl-5-fluoroisoxazoles, Regioselectivity
College of Natual Science and Mathematics, Chemistry and Biochemistry
A new method for the synthesis of 3-aryl-5-fluoroisoxazoles via the reaction of nitrosonium chlorosulfate with 2-aryl-1-bromo-1-fluorocyclopropanes containing acceptor substituents in the aromatic ring has been developed. The reaction proceeds highly regioselectively thus providing 3-aryl-5-fluoroisoxazoles in good yields. The structure of isoxazoles was corroborated by the DU8+ hybrid DFT/parametric computational approach.
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Bondarenko, O. B., Vinogradov, A. A., Komarov, A. I., Karetnikov, G. L., Zyk, N. V., Holt, T., & Kutateladze, A. G. (2019). Access to 5-fluoroisoxazoles via the nitrosation of geminal bromo-fluoro arylcyclopropanes. Tetrahedron, 75(20), 2861-2865. DOI: 10.1016/j.tet.2019.03.054.