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Transamidation of Carboxamides Catalyzed by Fe(III) and Water

Liliana Becerra-Figueroa , Andrea Ojeda-Porras and Diego Gamba-Sánchez*

*Laboratory of Organic Synthesis, Bio and Organocatalysis, Chemistry Department, Universidad de los Andes, Cra 1 No. 18A-12 Q:305, Bogotá 111711, Colombia, Email: da.gamba1361uniandes.edu.co

L. Becerra-Figueroa , A. Ojeda-Porras, D. Gamba-Sánchez, J. Org. Chem., 2014, 79, 4544-4552.

DOI: 10.1021/jo500562w (free Supporting Information)


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Abstract

A highly efficient transamidation of several primary, secondary, and tertiary amides with aliphatic and aromatic amines (primary and secondary) is performed in the presence of a 5 mol % concentration of different hydrated salts of Fe(III). The methodology was also applied to urea and phthalimide to demonstrate its versatility and wide substrate scope. A plausible mechanism explains the crucial role of water.

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Key Words

Amides, Phthalimides


ID: J42-Y2014