Organic Chemistry

On the N-Arylation of Acetamide Using 2-, 3- and 1’-Substituted Iodoferrocenes


Various 2-, 3- and 1’-substituted iodoferrocenes were
reacted with acetamide in the presence of copper(I) iodide (1
equiv), N,N’-dimethylethylenediamine (1 equiv), tripotassium
phosphate (2 equiv) in dioxane at 90 °C for 14 h, and allowed a large range of original 1,2-, 1,3- and 1,1’-disubstituted ferrocenes to be obtained. The results were compared as a function of the substituent and its position on the ring. DFT calculations revealed higher activation barrier for the oxidative addition in the ferrocene series when compared with classical planar aromatics. Structure–property relationships were applied to rationalize the reactivity of the different iodoferrocenes.


Thumbnail image of main amidation FcI Erb.pdf