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在六氟异丙醇中富电子仲苄醇的官能团化:从硫醚到三取代甲烷

Functionalization of Electron-Rich Secondary Benzyl Alcohols in HFIP: From Thioethers to Trisubstituted Methanes.

作者信息

Markwitz Martyna, Labrzycki Klaudiusz, Łyczek Kacper, Kuciński Krzysztof

机构信息

Faculty of Chemistry, Adam Mickiewicz University, Poznań, Uniwersytetu Poznańskiego St. 8, Poznań 61-614, Poland.

出版信息

J Org Chem. 2025 Jul 11;90(27):9513-9518. doi: 10.1021/acs.joc.5c00900. Epub 2025 Jun 28.

DOI:10.1021/acs.joc.5c00900
PMID:40580135
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12261332/
Abstract

To date, C-S bond formation via dehydration of electron-rich secondary benzylic alcohols has been limited to catalytic approaches. In this work, we developed an efficient method for synthesizing various thioethers by employing hexafluoroisopropanol (HFIP) as a solvent. This approach also enables the functionalization of secondary benzyl alcohols with other important organic molecules, such as allylsilanes, activated arenes, and indoles, leading to various trisubstituted methanes, including 14 novel products in total.

摘要

迄今为止,通过富电子仲苄醇脱水形成C-S键的方法仅限于催化方法。在这项工作中,我们开发了一种以六氟异丙醇(HFIP)为溶剂合成各种硫醚的有效方法。该方法还能使仲苄醇与其他重要有机分子(如烯丙基硅烷、活性芳烃和吲哚)发生官能团化反应,生成各种三取代甲烷,总共包括14种新产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1495/12261332/c1f127942091/jo5c00900_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1495/12261332/bc4f2a3cf061/jo5c00900_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1495/12261332/626406b10a8f/jo5c00900_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1495/12261332/c1f127942091/jo5c00900_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1495/12261332/bc4f2a3cf061/jo5c00900_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1495/12261332/626406b10a8f/jo5c00900_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1495/12261332/c1f127942091/jo5c00900_0003.jpg

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本文引用的文献

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