Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides

A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.

Automated summary

A new electrochemical method has been developed to prepare isocyanides from readily available aminotetrazole derivatives, which can tolerate a wide range of functional groups. Additionally, it was demonstrated that isocyanides can also be obtained through chemical oxidation, providing access to these compounds for those without electrosynthesis equipment. The feasibility of scaling up production using flow electrochemistry, as well as the potential use of electrochemically generated isocyanides in further reactions, has been also demonstrated.