New synthetic “tricks”. Triphenylphosphine-mediated amide formation from carboxylic acids and azides |
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| Authors: | Jordi Garcia Fèlix Urpí Jaume Vilarrasa |
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| Institution: | Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Catolonia Spain |
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| Abstract: | Equimolar amounts of carboxylic acids, aryl or alkyl azides, and Ph3P in refluxing benzene (hexane, toluene) afford amides in good yields. Insolubility of zwitterions Ph3P+-NH(CH2)nCOO-, arising from μ-azido acids and Ph3P, limits the utilization of the method for lactame formation. |
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