期刊
ORGANIC PROCESS RESEARCH & DEVELOPMENT
卷 25, 期 12, 页码 2614-2621出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.1c00112
关键词
isocyanates; electrosynthesis; urea; carbamates; phosgene-free; flow electrosynthesis; anodic decarboxylation; oxamic acids
资金
- Engineering and Physical Sciences Research Council [EP/S017097/1]
- University of Greenwich
- University Alliance Applied Biosciences for Health (Marie Skodowska-Curie Grant) [801604]
- Natural Sciences and Engineering Research Council of Canada (NSERC) [PGSD3-546986-2020]
- Royal Society of Chemistry [M19-0357]
- Marie Curie Actions (MSCA) [801604] Funding Source: Marie Curie Actions (MSCA)
This new method enables the synthesis of ureas, carbamates, and thiocarbamates in a simple and practical way, applicable to various substrates. The use of continuous electrochemical flow conditions allows for high yield synthesis, making the process easily scalable.
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 C-gr/C-gr 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.
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