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

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.