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三氯乙腈作为一种有效的活化剂,用于芳基硼酸的原位羟基化反应,生成酚类化合物。

Trichloroacetonitrile as an efficient activating agent for the ipso-hydroxylation of arylboronic acids to phenolic compounds.

机构信息

School of Science, Harbin Institute of Technology, Shenzhen, 518055, China and MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China.

MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China.

出版信息

Org Biomol Chem. 2019 Aug 28;17(32):7558-7563. doi: 10.1039/c9ob01568j. Epub 2019 Aug 2.

DOI:10.1039/c9ob01568j
PMID:31373339
Abstract

A metal-free and base-free ClCCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.

摘要

一种无金属和无碱的 ClCCN 介导方法被开发用于芳基硼酸的原位羟基化生成相应的酚,该反应由关键的不稳定路易斯加合物中间体促进。这种转化具有广泛的官能团容忍性,并且后期的官能团化也取得了成功。经过简单的研究,提出了两种途径(自由基/离子机制),并且需要进一步研究蓝光的有益作用。

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