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温和反应条件下芳基锍盐的羟基化用于苯酚合成

Hydroxylation of Aryl Sulfonium Salts for Phenol Synthesis under Mild Reaction Conditions.

作者信息

Hu Xuan-Bo, Fu Qian-Qian, Huang Xue-Ying, Chu Xue-Qiang, Shen Zhi-Liang, Miao Chengping, Chen Weiyi

机构信息

Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, China.

出版信息

Molecules. 2024 Feb 13;29(4):831. doi: 10.3390/molecules29040831.

DOI:10.3390/molecules29040831
PMID:38398583
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10891898/
Abstract

Hydroxylation of aryl sulfonium salts could be realized by utilizing acetohydroxamic acid and oxime as hydroxylative agents in the presence of cesium carbonate as a base, leading to a variety of structurally diverse hydroxylated arenes in 47-95% yields. In addition, the reaction exhibited broad functionality tolerance, and a range of important functional groups (e.g., cyano, nitro, sulfonyl, formyl, keto, and ester) could be well amenable to the mild reaction conditions.

摘要

在碳酸铯作为碱的存在下,利用乙酰氧肟酸和肟作为羟基化试剂,可以实现芳基锍盐的羟基化反应,从而以47-95%的产率得到各种结构多样的羟基化芳烃。此外,该反应表现出广泛的官能团耐受性,一系列重要的官能团(如氰基、硝基、磺酰基、甲酰基、酮基和酯基)都能很好地适应温和的反应条件。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b9f/10891898/c9c0ae8236ad/molecules-29-00831-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b9f/10891898/aff6d8987167/molecules-29-00831-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b9f/10891898/32e72b963262/molecules-29-00831-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b9f/10891898/c9c0ae8236ad/molecules-29-00831-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b9f/10891898/aff6d8987167/molecules-29-00831-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b9f/10891898/32e72b963262/molecules-29-00831-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b9f/10891898/c9c0ae8236ad/molecules-29-00831-g001.jpg

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A Facile and General Oxidative Hydroxylation of Organoboron Compounds: Citric Acid as an Efficient Catalyst in Water to Access Phenolic and Alcoholic Motifs.有机硼化合物的简便通用氧化羟基化反应:柠檬酸作为水中高效催化剂用于构建酚类和醇类结构单元
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C(sp)-H Hydroxylation via Catalytic 1,4-Ni Migration with NO.
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J Am Chem Soc. 2023 Aug 16;145(32):17564-17569. doi: 10.1021/jacs.3c07018. Epub 2023 Aug 2.
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Modification of the 4-Hydroxyphenylacetate-3-hydroxylase Substrate Pocket to Increase Activity towards Resveratrol.修饰 4-羟基苯乙酸-3-羟化酶的底物口袋以增加其对白藜芦醇的活性。
Molecules. 2023 Jul 24;28(14):5602. doi: 10.3390/molecules28145602.
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