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Zirconium-Catalyzed Synthesis of 6-(Trifluoromethyl)-2H-pyran-2-ones via C-C Bond Cleavage
Zipeng Zhang1,2, Yangjie Huang1, Zihang Yuan2
1Fujian Provincial University Engineering Research Center of Green Materials and Chemical Engineering, and Fujian Engineering Research Center of New Chinese Lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou 350108, China.
Abstract:
A strategy for the annulation reaction of alkynones with ethyl 4,4,4-trifluoro-3-oxobutanoate through C-C bond cleavage is described. The zirconium-catalyzed transformation provides access to a wide range of structurally diverse 6-(trifluoromethyl)-2H-pyran-2-ones in moderate to good yields, utilizing Na2CO3 as a base. Further transformations into trifluoromethylated arene derivatives have been demonstrated as well. Furthermore, plausible reaction pathways are proposed by conducting various control experiments and isolating a β-diketone intermediate (X-ray) containing an intramolecular hydrogen bond.
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