Electrochemical NaI-mediated one-pot synthesis of guanidines from isothiocyanates via tandem addition-guanylation

In this study, we present an electrochemical approach for the synthesis of guanidines from isothiocyanates and amines in a single reaction vessel. This one-pot operation takes place in aqueous media, utilizing an undivided cell setup with NaI serving as both the electrolyte and mediator. The process involves the in situ generation of thiourea, followed by electrolytic guanylation with amines. Under ambient temperature conditions, we successfully demonstrated the formation of 30 different guanidine compounds, achieving yields ranging from fair to excellent. Furthermore, the synthesis method could be carried out on a gram scale with a good yield. This protocol stands out for its cost-effectiveness, step-economical design, high tolerance towards various functional groups, and environmentally friendly reaction conditions.

Automated summary

In this study, an electrochemical approach for the synthesis of guanidines from isothiocyanates and amines in a single reaction vessel is presented. The one-pot operation takes place in aqueous media with NaI serving as both the electrolyte and mediator. The process involves in situ generation of thiourea followed by electrolytic guanylation with amines. Under ambient temperature conditions, the formation of 30 different guanidine compounds with yields ranging from fair to excellent has been successfully demonstrated. This cost-effective and environmentally friendly synthesis method shows high tolerance towards various functional groups.