On the N‐Arylation of Acetamide Using 2‐, 3‐ and 1'‐Substituted Iodoferrocenes.

Kadari, Lingaswamy; Erb, William; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Lyakhov, Dmitry; Roisnel, Thierry; Radha Krishna, Palakodety; Mongin, Florence

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.

ACETAMIDE; OXIDATIVE addition; DIOXANE; FERROCENE; COPPER; ACETAMIDE derivatives; AMIDES

European Journal of Inorganic Chemistry, 2021, Vol 2021, Issue 4, p377

1434-1948

Academic Journal

10.1002/ejic.202000904