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通过直接电解实现芳基卤化物的加氢脱卤反应。

Hydrodehalogenation of Aryl Halides through Direct Electrolysis.

作者信息

Ke Jie, Wang Hongling, Zhou Liejin, Mou Chengli, Zhang Jingjie, Pan Lutai, Chi Yonggui Robin

机构信息

Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.

Guiyang College of Traditional Chinese Medicine, Guizhou, P.R. China.

出版信息

Chemistry. 2019 May 17;25(28):6911-6914. doi: 10.1002/chem.201901082. Epub 2019 Apr 26.

Abstract

A catalyst- and metal-free electrochemical hydrodehalogenation of aryl halides is disclosed. Our reaction by a flexible protocol is operated in an undivided cell equipped with an inexpensive graphite rod anode and cathode. Trialkylamines nBu N/Et N behave as effective reductants and hydrogen atom donors for this electrochemical reductive reaction. Various aryl and heteroaryl bromides worked effectively. The typically less reactive aryl chlorides and fluorides can also be smoothly converted. The utility of our method is demonstrated by detoxification of harmful pesticides and hydrodebromination of a dibrominated biphenyl (analogues of flame-retardants) in gram scale.

摘要

公开了一种无催化剂和金属的芳基卤化物电化学加氢脱卤反应。我们的反应通过灵活的方案在配备廉价石墨棒阳极和阴极的无隔膜电池中进行。三烷基胺nBu₃N/Et₃N作为这种电化学还原反应的有效还原剂和氢原子供体。各种芳基和杂芳基溴化物都能有效反应。通常反应活性较低的芳基氯化物和氟化物也能顺利转化。我们方法的实用性通过对有害农药的解毒以及克级规模的二溴联苯(阻燃剂类似物)的加氢脱溴得以证明。

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