eCyanation Using\n5‑Aminotetrazole As a Safer\nElectrophilic and Nucleophilic Cyanide Source

An electrochemical method for carrying out safer cyanation\nreactions\nis reported. The use of 5-aminotetrazole as a cyanide source enabled\nthe successful electrogeneration of both electrophilic and nucleophilic\ncyanide sources. To demonstrate the versatility of the method, a variety\nof cyanation reactions were carried out, including the synthesis of\ncyanamides, <i>N</i>-heterocycles, and aromatic nitriles,\nas well as the nucleophilic addition of cyanides to a variety of electrophiles\nwithout the need to handle highly toxic cyanide salts. Finally, as\na proof of concept for scalability, the cyanation methodology was\nrapidly transferred to a flow electrosynthesis setup, which demonstrated\nits potential for large-scale applications.