Zirconium-Catalyzed Synthesis of 6-(Trifluoromethyl)-2-pyran-2-ones via C-C Bond Cleavage.
作者信息
Zhang Zipeng, Huang Yangjie, Yuan Zihang, Xia Jianrong, Weng Zhiqiang
机构信息
Fujian 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.
Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou 350108, China.
出版信息
J Org Chem. 2024 Apr 19;89(8):5683-5689. doi: 10.1021/acs.joc.4c00227. Epub 2024 Apr 3.
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)-2-pyran-2-ones in moderate to good yields, utilizing NaCO 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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