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A Straightforward Synthesis of N-Substituted Ureas from Primary Amides

Author:
Rosa, Nathalie Saraiva  Glachet, Thomas  Ibert, Quentin  Lohier, Jean-Francois  Franck, Xavier  Reboul, Vincent  


Journal:
SYNTHESIS-STUTTGART


Issue Date:
2020


Abstract(summary):

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.


Page:
2099---2105


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