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Article Dans Une Revue European Journal of Inorganic Chemistry Année : 2021

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

Résumé

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 degrees 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.
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Dates et versions

hal-03122470 , version 1 (05-02-2021)

Identifiants

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Lingaswamy Kadari, William Erb, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, et al.. On the N-Arylation of Acetamide Using 2-, 3-and 1'-Substituted Iodoferrocenes. European Journal of Inorganic Chemistry, 2021, 2021 (4), pp.377-391. ⟨10.1002/ejic.202000904⟩. ⟨hal-03122470⟩
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