Stereoselective synthetic approach toward β-trifluoromethyl vinyl ethers and diethers via reaction of (E)-1,2-dichloro-3,3,3-trifluoroprop-1-ene with phenols†

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-09-16 DOI:10.1039/d4ob01254b

Yu An , Xiao-Bo Tang , Dong-Wei Sun , Ting-Ting Meng , Bo Zhao , Sheng Han , Zhi-Qiang Yang , Wei Zhang , Nian Tang , Ji-Jun Zeng , Jian Lu

引用次数: 0

Abstract

A convenient method for synthesizing β-trifluoromethyl vinyl ethers and diethers through the base-mediated C–O coupling of (E)-1,2-dichloro-3,3,3-trifluoroprop-1-ene and phenols has been developed. Remarkably, the present process shows perfect regioselective and stereoselective yield of the Z/E isomers for β-trifluoromethyl vinyl ethers with high efficiency. Additionally, β-trifluoromethyl vinyl diethers with identical/diverse phenoxy groups were also obtained and the regulation of the product configuration was achieved. These reactions feature transition-metal-free conditions, wide substrate scope, and atom economy.

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通过(E)-1,2-二氯-3,3,3-三氟丙烯与苯酚的反应，立体选择性合成 β-三氟甲基乙烯基醚和二醚。

通过碱介导的 (E)-1,2-dichloro-3,3,3-trifluoroprop-1-ene 和苯酚的 C-O 偶联，开发出了一种合成 β-三氟甲基乙烯基醚和二醚的简便方法。值得注意的是，本工艺对 β-三氟甲基乙烯基醚的 Z/E 异构体具有完美的区域选择性和立体选择性，而且效率很高。此外，还获得了具有相同/不同苯氧基的 β-三氟甲基乙烯基二醚，并实现了对产物构型的调节。这些反应具有无过渡金属条件、底物范围广和原子经济等特点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.