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

被引：1
|
作者：
Zhang, Zipeng [1 ,2 ,3 ]
Huang, Yangjie [1 ,2 ]
Yuan, Zihang [3 ]
Xia, Jianrong [1 ,2 ]
Weng, Zhiqiang [1 ,2 ,3 ]
机构：
[1] Minjiang Univ, Fujian Prov Univ, Coll Mat & Chem Engn, Engn Res Ctr Green Mat & Chem Eng, Fuzhou 350108, Peoples R China
[2] Minjiang Univ, Fujian Engn Res Ctr New Chinese Lacquer Mat, Fuzhou 350108, Peoples R China
[3] Fuzhou Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 08期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; ALPHA-PYRONES; INSERTION;
D O I：
10.1021/acs.joc.4c00227
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 beta-diketone intermediate (X-ray) containing an intramolecular hydrogen bond.
引用
收藏
页码：5683 / 5689
页数：7
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