eCyanation Using 5-Aminotetrazole As a Safer Electrophilic and Nucleophilic Cyanide Source.

An electrochemical method for carrying out safer cyanation reactions is reported. The use of 5-aminotetrazole as a cyanide source enabled the successful electrogeneration of both electrophilic and nucleophilic cyanide sources. To demonstrate the versatility of the method, a variety of cyanation reactions were carried out, including the synthesis of cyanamides, N-heterocycles, and aromatic nitriles, as well as the nucleophilic addition of cyanides to a variety of electrophiles without the need to handle highly toxic cyanide salts. Finally, as a proof of concept for scalability, the cyanation methodology was rapidly transferred to a flow electrosynthesis setup, which demonstrated its potential for large-scale applications.