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

Peter W Seavill; Katherine B Holt; Jonathan D Wilden

doi:10.1039/c9ra06782e

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

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

Authors

Peter W Seavill¹, Katherine B Holt¹, Jonathan D Wilden¹

Affiliation

¹ Department of Chemistry, University College London 20 Gordon Street London WC1H 0AJ UK pseavill@gmail.com j.wilden@ucl.ac.uk.

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.