Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2-Alkynone O-Methyl Oximes
The Journal of Organic Chemistry2014Vol. 79(14), pp. 6444–6455
Citations Over TimeTop 10% of 2014 papers
Abstract
A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.
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