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: https://orcid.org/0000-0002-7241-7118, Ollevier, Thierry and Lam, Kevin ORCID: https://orcid.org/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, 25 (12). pp. 2614-2621. ISSN 1083-6160 (Print), 1520-586X (Online) (doi: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 / School / Research Centre / Research Group:	Faculty of Engineering & Science Faculty of Engineering & Science > School of Science (SCI)
Last Modified:	20 May 2022 01:38
URI:	http://gala.gre.ac.uk/id/eprint/32850

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