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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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https://hal-normandie-univ.archives-ouvertes.fr/hal-02569464
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Submitted on : Wednesday, July 21, 2021 - 11:05:48 AM
Last modification on : Tuesday, January 4, 2022 - 5:59:46 AM

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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, 52 (14), pp.2099-2105. ⟨10.1055/s-0040-1707103⟩. ⟨hal-02569464⟩

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