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

preprint
submitted on 17.09.2020 and posted on 18.09.2020 by Lingaswamy Kadari, William Erb, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Dmitry Lyakhov, Thierry Roisnel, Palakodety Radha Krishna, Florence Mongin
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.

Funding

Université de Rennes 1

CNRS

Rennes Métropole

Région Bretagne

FEDER

Thermofisher

History

Email Address of Submitting Author

william.erb@univ-rennes1.fr

Institution

Université de Rennes 1

Country

France

ORCID For Submitting Author

0000-0002-2906-2091

Declaration of Conflict of Interest

No conflict to declare.

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