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Facile Amide Bond Formation from Carboxylic Acids and Isocyanates

Kaname Sasaki and David Crich*

*Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif-sur-Yvette, France, Email: dcrichicsn.cnrs-gif.fr

K. Sasaki, D. Crich, Org. Lett., 2011, 13, 2256-2259.

DOI: 10.1021/ol200531k (free Supporting Information)


Abstract

Aliphatic, aromatic, and heteroaromatic carboxylic acids in the form of their salts condense with aryl isocyanates at room temperature with loss of carbon dioxide to give the corresponding amides in high yield. Application of the reaction to acyl isocyanates gives unsymmetric imides. The reaction is compatible with hydroxyl groups and both Fmoc and Boc protecting groups for amines.

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Key Words

Amides


ID: J54-Y2011-1270