Optimization of the Conditions for Copper‐Mediated <i>N</i>‐Arylation of Heteroarylamines

Abstract

Abstract Simple and inexpensive copper‐mediated N ‐arylation ofheteroarylamines was achieved by using N , N ′‐dimethylethylenediamine as a ligand and K 2 CO 3 as a base in dioxane heated at 100 °C. In this coupling reaction, the influence of the copper species, ligand, base and solvent was investigated in detail. N ‐Arylated derivatives of several heteroarylamines were synthesized under optimized reaction conditions, and all the products were isolated in good yields. By controlling the amount of CuI/DMEDA added, heteroarylamines with weak nucleophilic activity were coupled with aryl iodides or aryl bromides. The activity of the copper catalyst for this C–N bond‐forming reaction follows the order Cu I &gt; Cu 0 &gt; Cu II . (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2007)