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由1,3-苯并二恶唑电化学合成氟化原酸酯

Electrochemical Synthesis of Fluorinated Orthoesters from 1,3-Benzodioxoles.

作者信息

Röckl Johannes L, Hauck Adrian V, Schollmeyer Dieter, Waldvogel Siegfried R

机构信息

Johannes Gutenberg University Mainz Institute of Organic Chemistry Duesbergweg 10-14 55128 Mainz Germany.

Johannes Gutenberg Universität Mainz Graduate School Materials Science in Mainz Staudingerweg 9 55128 Mainz Germany.

出版信息

ChemistryOpen. 2019 May 14;8(9):1167-1171. doi: 10.1002/open.201900127. eCollection 2019 Sep.

DOI:10.1002/open.201900127
PMID:31497470
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6718074/
Abstract

A scalable, dehydrogenative, and electrochemical synthesis of novel highly fluorinated orthoesters is reported. This protocol provides easy and direct access to a wide variety of derivatives, using a very simple electrolysis setup. These compounds are surprisingly robust towards base and acid with an unusual high lipophilicity, making them interesting motifs for potentially active compounds in medicinal chemistry or agro applications. The use of electricity enables a safe and environmentally benign chemical transformation as only electrons serve as oxidants.

摘要

报道了一种可扩展的、脱氢的电化学合成新型高氟化原酸酯的方法。该方案使用非常简单的电解装置，能轻松直接地获得多种衍生物。这些化合物对碱和酸具有惊人的稳定性，且具有异常高的亲脂性，使其成为药物化学或农业应用中潜在活性化合物的有趣结构单元。用电实现了安全且环境友好的化学转化，因为仅电子作为氧化剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1144/6718074/9487b38786a3/OPEN-8-1167-g008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1144/6718074/9487b38786a3/OPEN-8-1167-g008.jpg

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3
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Angew Chem Int Ed Engl. 2020 Jan 2;59(1):315-319. doi: 10.1002/anie.201910077. Epub 2019 Nov 19.
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5
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6
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7
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8
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10
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