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Supporting-electrolyte-free anodic oxidation of oxamic acids into isocyanates: an expedient way to access ureas, carbamates, and thiocarbamates

Supporting-electrolyte-free anodic oxidation of oxamic acids into isocyanates: an expedient way to access ureas, carbamates, and thiocarbamates

Petti, Alessia, Fagnan, Corentin, van Melis, Carlo G. W., Tanbouza, Nour, Garcia, Anthony D., Mastrodonato, Andrea, Leech, Matthew C., Goodall, Iain C. A., Dobbs, Adrian P. ORCID: 0000-0002-7241-7118, Ollevier, Thierry and Lam, Kevin ORCID: 0000-0003-1481-9212 (2021) Supporting-electrolyte-free anodic oxidation of oxamic acids into isocyanates: an expedient way to access ureas, carbamates, and thiocarbamates. Organic Process Research & Development. ISSN 1083-6160 (Print), 1520-586X (Online) (In Press) (doi:https://doi.org/10.1021/acs.oprd.1c00112)

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Abstract

We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.

Item Type: Article
Uncontrolled Keywords: radials, electrosynthesis, electrochemistry, isocyanate
Subjects: Q Science > Q Science (General)
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 16 Jun 2021 10:19
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
Selected for REF2021: None
URI: http://gala.gre.ac.uk/id/eprint/32850

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