Aminolysis of aryl ester using tertiary amine as amino donor via C-O and C-N bond activations

J Org Chem. 2014 Jan 17;79(2):803-8. doi: 10.1021/jo4023974. Epub 2013 Dec 31.

Abstract

An aminolysis reaction between various aryl esters and inert tertiary amines by C-O and C-N bond activations has been developed for the selective synthesis of a broad scope of tertiary amides under neutral and mild conditions. The mechanism may undergo the two key steps of oxidative addition of acyl C-O bond in parent ester and C-N bond cleavage of tertiary amine via an iminium-type intermediate.