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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 (NH3 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.
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Contributor : Madeleine Roux-Merlin <>
Submitted on : Monday, May 11, 2020 - 1:13:24 PM
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Nathalie Saraiva Rosa, Thomas Glachet, Quentin Ibert, Jean-François Lohier, Xavier Franck, et al.. A Straightforward Synthesis of N-Substituted Ureas from Primary Amides. SYNTHESIS, Georg Thieme Verlag, 2020, (in press). ⟨10.1055/s-0040-1707103⟩. ⟨hal-02569464⟩



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