Catalyst‐Free Preparation of Perfluoroalkyl‐Phosphoryl Substituted Furans from 1‐Perfluoroalkyl 1,3‐Diketones in Two Steps,Advanced Synthesis & Catalysis

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Catalyst‐Free Preparation of Perfluoroalkyl‐Phosphoryl Substituted Furans from 1‐Perfluoroalkyl 1,3‐Diketones in Two Steps
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-06-02 , DOI: 10.1002/adsc.202000534
Stanislav V. Lozovskiy ₁ , Aleksander V. Vasilyev _{1,

2}

Affiliation

A two‐step catalyst‐free procedure for the construction of 3‐perfluoroalkyl‐2‐(phosphoryl)methyl furans from commercially available 1‐perfluoroalkyl 1,3‐diketones is reported. Propargylic alcohols, prepared by direct alkynylation of the diketones, react with PCl₃ via [2,3]‐sigmatropic rearrangement – enolate cyclization sequence, leading to multifunctional furans. The reaction mechanism is supported by DFT study. In addition, the bioactivity modifying effect of phosphoryl group on 3‐perfluoroalkyl furans is depicted.

中文翻译：

分两步从1-全氟烷基1,3-二酮无催化剂制备全氟烷基-磷酰基取代的呋喃

据报道，从市售的1-全氟烷基1,3-二酮类化合物制备三-全氟烷基-2-（磷酰基）甲基呋喃需要两步操作，无需催化剂。通过二酮的直接烷基化制备的炔丙醇通过[2,3] -sigmatropic重排（烯醇化环化序列）与PCl ₃反应，生成多功能呋喃。反应机理得到DFT研究的支持。此外，还描述了磷酸基对3-全氟烷基呋喃的生物活性改性作用。

更新日期：2020-08-04

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