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Access to 5-fluoroisoxazoles via the nitrosation of geminal bromo-fluoro arylcyclopropanes

Oksana B. Bondarenko,Aleksandr A. Vinogradov,Arseniy I. Komarov,Georgy L. Karetnikov,Nikolai V. Zyk,Tina Holt,Andrei G. Kutateladze

Tetrahedron（2019）

Cited 7|Views25
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Abstract
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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Key words
2-Aryl-1-bromo-1-fluorocyclopropanes,Nitrosonium chlorosulfate,3-Aryl-5-fluoroisoxazoles,Regioselectivity
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