A Straightforward Synthesis of N-Substituted Ureas from Primary Amides

Abstract A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2020-07, Vol.52 (14), p.2099-2105
Main Authors: Saraiva Rosa, Nathalie, Glachet, Thomas, Ibert, Quentin, Lohier, Jean-François, Franck, Xavier, Reboul, Vincent
Format: Article
Language:English
Subjects:
Chemical Sciences
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Summary:Abstract A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1707103