Amidations using N, N'-carbonyldiimidazole: Remarkable rate enhancement by carbon dioxide

R Vaidyanathan, VG Kalthod, DP Ngo…

Index: Vaidyanathan, Rajappa; Kalthod, Vikram G.; Ngo, Duc P.; Manley, Jerad M.; Lapekas, Sean P. Journal of Organic Chemistry, 2004 , vol. 69, # 7 p. 2565 - 2568

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Citation Number: 44

Abstract

N,N '-Carbonyldiimidazole (CDI, 1) is a widely used reagent to form amides from carboxylic acids and amines (Scheme 1). 1 Typically, this is a one-pot procedure wherein a mixture of the acid and CDI is allowed to stir until the activation reaction to form the intermediate imidazolide 2 is complete. The amine is then added to the reaction mixture to lead to the desired amide. The method has been applied to a variety of aliphatic, aromatic, and heterocyclic carboxylic ...