Zirconium-Catalyzed Synthesis of 6‑(Trifluoromethyl)‑2H‑pyran-2-ones via C–C Bond Cleavage

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, utilizi...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-04, Vol.89 (8), p.5683-5689
Main Authors: Zhang, Zipeng, Huang, Yangjie, Yuan, Zihang, Xia, Jianrong, Weng, Zhiqiang
Format: Article
Language:English
Online Access:Get full text
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00227