Modular Synthesis of Furans with Four Nonidentical Substituents by Aqueous Defluorinative Reaction of Trifluoromethyl Enones with Two Nucleophiles

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-24 DOI:10.1021/acs.orglett.4c04488

Xue-Ying Huang, Shu-Ji Gao, Danhua Ge, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu

引用次数: 0

Abstract

A three-component reaction of trifluoromethyl enones, phosphine oxides, and alcohols in water solution is developed. This defluorinative reaction occurs through a cascade process involving defluorophosphorylation, defluoroalkyloxylation, and defluoroheteroannulation, enabling the modular synthesis of furans with four distinct substituents: C2-alkyloxy, C3-trifluoromethyl, C4-phosphoryl, and C5-(hetero)aryl groups. Moreover, apart from alcohol substrates, the scope of nucleophiles could be further extended to phenols, azacycles, or sulfonamide.

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三氟甲基烯酮与两种亲核试剂的水脱氟反应模块化合成含四个不同取代基的呋喃

研究了三氟甲基烯酮、氧化膦和醇在水溶液中的三组分反应。这种去氟化反应通过一个涉及去氟磷酸化、去氟烷基氧基化和去氟杂环化的级联过程发生，从而能够模块化合成具有四种不同取代基的呋喃：c2 -烷基、c3 -三氟甲基、c4 -磷酰基和C5-（杂）芳基。此外，除了醇类底物外，亲核试剂的范围还可以进一步扩展到酚类、氮杂环类或磺胺类。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.