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

页码：5683 / 5689

页数：7

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