Copper(II)-catalysed hydrolysis of an unactivated amide. Application of the groves' rule to the hydrolysis of acrylamide

Abstract

Conjugate addition of N-benzyl-N′,N′-dimethylethylenediamine to acrylamide affords a chelating amide in which the amide carbonyl can coordinate to the bound metal only via a six-membered chelate; this compound demonstrates copper(II)-catalysed amide hydrolysis, in which each metal acts on at least five equivalents of substrate.