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芳基硼酸无催化剂和无溶剂的羟基化反应生成酚类

Catalyst- and solvent-free -hydroxylation of arylboronic acids to phenols.

作者信息

Yang Xiufang, Jiang Xulu, Wang Weitao, Yang Qi, Ma Yangmin, Wang Kuan

机构信息

College of Chemistry & Chemical Engineering, Shaanxi University of Science & Technology Xi'an Shaanxi 710021 China

Shaanxi Key Laboratory of Chemical Additives for Industry, Shaanxi University of Science & Technology Xi'an Shaanxi 710021 China.

出版信息

RSC Adv. 2019 Oct 25;9(59):34529-34534. doi: 10.1039/c9ra07201b. eCollection 2019 Oct 23.

DOI:10.1039/c9ra07201b
PMID:35529971
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9074145/
Abstract

A catalyst-free method for the hydroxylation of arylboronic acids to form the corresponding phenols with sodium perborate as the oxidant was developed using water as the solvent. Under the reaction conditions, the yield of phenol reached 92% at only 5 min. Moreover, the reaction could be conducted without a catalyst under the solvent-free condition, the efficiency of which was as high as that of a liquid-phase reaction. Using a microcalorimeter, the reaction was found to be an exothermic reaction. The reaction mechanism was investigated and understood DFT calculations, which revealed that it was a nucleophilic reaction.

摘要

开发了一种以水为溶剂、过硼酸钠为氧化剂将芳基硼酸羟基化以形成相应酚类的无催化剂方法。在该反应条件下,仅5分钟苯酚产率就达到了92%。此外,该反应在无溶剂条件下无需催化剂即可进行,其效率与液相反应一样高。使用微量热计,发现该反应是放热反应。通过密度泛函理论(DFT)计算对反应机理进行了研究并得到理解,结果表明这是一个亲核反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/e0dda89a2eb5/c9ra07201b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/77bbbc44a76b/c9ra07201b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/acc84fd15320/c9ra07201b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/dd06c9418b68/c9ra07201b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/0a5020fd9794/c9ra07201b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/4474ec09f8d2/c9ra07201b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/6b51b685a0f7/c9ra07201b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/e0dda89a2eb5/c9ra07201b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/77bbbc44a76b/c9ra07201b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/acc84fd15320/c9ra07201b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/dd06c9418b68/c9ra07201b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/0a5020fd9794/c9ra07201b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/4474ec09f8d2/c9ra07201b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/6b51b685a0f7/c9ra07201b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/135a/9074145/e0dda89a2eb5/c9ra07201b-f4.jpg

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