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在水中使用卤化钠通过NCS介导的芳基硼酸的卤化反应

NCS-Mediated -Halogenation of Arylboronic Acids in Water Using Sodium Halides.

作者信息

Santarsiere Alessandro, Galgano Pierantonio, Funicello Maria, Lupattelli Paolo, Chiummiento Lucia

机构信息

Department of Basic and Applied Sciences, University of Basilicata, Via dell'Ateneo lucano 10, Potenza 85100, Italy.

Department of Chemistry, University "La Sapienza" of Roma, Piazzale A. Moro 5, Roma 00185, Italy.

出版信息

ACS Omega. 2025 Jun 25;10(26):27856-27860. doi: 10.1021/acsomega.5c00755. eCollection 2025 Jul 8.

DOI:10.1021/acsomega.5c00755
PMID:40657073
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12242620/
Abstract

A mild, efficient, eco-friendly method for the regioselective halogenation of arylboronic acids in water has been reported. A transition-metal-free -chlorination of arylboronic acids was performed in water, yielding aryl chlorides. -brominated and iodinated compounds were obtained under the same conditions using the corresponding halide salts. This eco-friendly method operates efficiently, even on activated or nonactivated systems, with good yields and selectivity.

摘要

已报道了一种温和、高效、环保的在水中对芳基硼酸进行区域选择性卤化的方法。在水中进行了芳基硼酸的无过渡金属氯化反应,生成芳基氯。在相同条件下使用相应的卤化物盐可得到溴化和碘化化合物。这种环保方法即使在活化或未活化的体系中也能高效运行,具有良好的产率和选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c26d/12242620/c8c199c8b581/ao5c00755_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c26d/12242620/a3267d4c562e/ao5c00755_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c26d/12242620/c8c199c8b581/ao5c00755_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c26d/12242620/a3267d4c562e/ao5c00755_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c26d/12242620/c8c199c8b581/ao5c00755_0002.jpg

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本文引用的文献

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Ecofriendly Protocol for -Bromination of Arylboronic Acids.
Org Lett. 2024 Jun 21;26(24):5151-5156. doi: 10.1021/acs.orglett.4c01570. Epub 2024 Jun 12.
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Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol.六氟异丙醇中芳烃和杂环的区域选择性卤化。
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