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电化学合成乙炔亚铜(I):同时电生成铜离子和催化碱用于点击化学。

Electrochemical synthesis of copper(i) acetylides simultaneous copper ion and catalytic base electrogeneration for use in click chemistry.

作者信息

Seavill Peter W, Holt Katherine B, Wilden Jonathan D

机构信息

Department of Chemistry, University College London 20 Gordon Street London WC1H 0AJ UK

出版信息

RSC Adv. 2019 Sep 17;9(50):29300-29304. doi: 10.1039/c9ra06782e. eCollection 2019 Sep 13.

Abstract

We report an efficient and sustainable electrochemical synthesis of copper(i) acetylides using simultaneous copper oxidation and Hofmann elimination of quaternary ammonium salts. The electrochemically-generated base was also regenerated electrochemically, making it catalytic. A 'Click test' (CuAAC reaction) was performed to assess product purity and an electrochemically-promoted, one-pot CuAAC reaction was performed, which serves as a promising initial demonstration of this approach in a pharmaceutically-relevant reaction.

摘要

我们报道了一种高效且可持续的电化学合成炔铜(I)的方法,该方法通过同时进行铜的氧化和季铵盐的霍夫曼消除反应来实现。电化学产生的碱也通过电化学方式进行再生,使其具有催化作用。进行了“点击测试”(铜催化的叠氮化物-炔烃环加成反应)以评估产物纯度,并进行了电化学促进的一锅法铜催化的叠氮化物-炔烃环加成反应,这是该方法在药物相关反应中颇具前景的初步证明。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80f4/9071997/b20831df8157/c9ra06782e-f1.jpg

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