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超强酸催化的脱氧氟化反应——质子化α-氟代羟基乙酸的合成与表征

Deoxyfluorination with superacids - synthesis and characterization of protonated α-fluorohydroxyacetic acid.

作者信息

Virmani Alan, Jessen Christoph, Nitzer Alexander, Kornath Andreas J

机构信息

Ludwig-Maximilians-Universität München Butenandtstraße 5-13 (D) D-81377 München Germany.

出版信息

RSC Adv. 2024 Oct 4;14(43):31517-31523. doi: 10.1039/d4ra05449k. eCollection 2024 Oct 1.

DOI:10.1039/d4ra05449k
PMID:39372048
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11450550/
Abstract

α-Fluoroalcohols describe a rare and unstable class of compounds, accessible mainly by fluorination of highly electrophilic carbonyl compounds. In this work, we report the syntheses of α-fluorohydroxyacetic acid (FHA) and its acyl fluoride (FHA-F) by reacting the dihydroxy species glyoxylic acid monohydrate (GAM) with SF. Surprisingly, only one of the geminal hydroxy groups is substituted when excess SF is employed. Implementing GAM with the binary superacid HF/AsF also leads to a single yet quantitative deoxyfluorination at the diol group. The reaction pathways are discussed based on NMR experiments, the characterization was carried out using NMR and vibrational spectroscopy as well as single-crystal X-ray diffraction.

摘要

α-氟代醇是一类罕见且不稳定的化合物，主要通过高亲电羰基化合物的氟化反应来制备。在本工作中，我们报道了通过使二羟基化合物一水合乙醛酸（GAM）与SF反应来合成α-氟代羟基乙酸（FHA）及其酰氟（FHA-F）。令人惊讶的是，当使用过量的SF时，仅偕二羟基中的一个被取代。用二元超强酸HF/AsF处理GAM也会导致二醇基团发生单一但定量的脱氧氟化反应。基于核磁共振实验讨论了反应途径，使用核磁共振、振动光谱以及单晶X射线衍射进行了表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/659798aca0b3/d4ra05449k-f4.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/2e63a1afb420/d4ra05449k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/77a74e25d26d/d4ra05449k-f2.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/4d030539f487/d4ra05449k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/55a868602228/d4ra05449k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/c7b714798f3d/d4ra05449k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/2e63a1afb420/d4ra05449k-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/1deab7c2d179/d4ra05449k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c83a/11450550/659798aca0b3/d4ra05449k-f4.jpg

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本文引用的文献

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Chemistry. 2024 Jul 19;30(41):e202400354. doi: 10.1002/chem.202400354. Epub 2024 Mar 6.
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The perfluorinated alcohols c-CFOH, c-CF-1,1-(OH) and c-CF-1-(CF)OH.
全氟醇 c-CFOH、c-CF-1、1-(OH) 和 c-CF-1-(CF)OH。
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