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,...

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Bibliographic Details
Published in:Organic letters 2021-12, Vol.23 (24), p.9371-9375
Main Authors: Leech, Matthew C, Petti, Alessia, Tanbouza, Nour, Mastrodonato, Andrea, Goodall, Iain C A, Ollevier, Thierry, Dobbs, Adrian P, Lam, Kevin
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03475