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

Seavill, PW; Holt, KB; Wilden, JD; (2019) Electrochemical synthesis of copper(i) acetylides: Via simultaneous copper ion and catalytic base electrogeneration for use in click chemistry. RSC Advances , 9 (50) pp. 29300-29304. 10.1039/c9ra06782e. Green open access

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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.

Type: Article
Title: Electrochemical synthesis of copper(i) acetylides: Via simultaneous copper ion and catalytic base electrogeneration for use in click chemistry
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c9ra06782e
Publisher version: https://doi.org/10.1039/c9ra06782e
Language: English
Additional information: This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10082718
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