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

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

Research output: Contribution to journalArticlepeer-review

Abstract

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.
Original languageEnglish (US)
JournalEuropean Journal of Inorganic Chemistry
DOIs
StatePublished - Dec 22 2020

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