Iodoferrocene as a partner in N -arylation of amides

Lingaswamy Kadari (1) , William Erb (1) , Thierry Roisnel (1) , Palakodety Radha Krishna (2) , Florence Mongin (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 IICT - CSIR Indian Institute of Chemical Technology

In this study, we developed a convenient methodology for the N-arylation of various acetamides, benzamides and related compounds by iodoferrocene. Optimization of the reaction was first performed from acetamide on the basis of the achievements in the benzene series. Next, the identified conditions (use of copper(I) iodide, N,N′-dimethylethylenediamine, tripotassium phosphate in dioxane at 90 °C for 14 h) were applied to different aliphatic/aromatic primary and cyclic/acyclic secondary amides in order to determine the scope of the reaction, thus easily generating a small library of ferrocene amides.

Domaines: Chimie

Lingaswamy Kadari, William Erb, Thierry Roisnel, Palakodety Radha Krishna, Florence Mongin. Iodoferrocene as a partner in N -arylation of amides. New Journal of Chemistry, 2020, 44 (37), pp.15928-15941. ⟨10.1039/D0NJ03470C⟩. ⟨hal-02949153⟩