Copper-Mediated Multiple C–H Functionalization of Aromatic <i>N</i>‑Heterocycles: Bromoamination of Indoles and Pyrroles

Abstract

A copper-mediated bromoamination of aromatic <i>N</i>-heterocycles has been achieved using oxime esters as the <i>N</i>-reagents under mild conditions (ca<i>.</i> 70 °C). The reaction with <i>N</i>-alkyl indoles proceeds regioselectively to produce the 2-amino-3-bromo indole derivatives as confirmed by X-ray crystallographic analysis of the bromoaminated product, <b>3aa-Br</b>. With <i>N</i>-methylpyrrole both the monobromoaminated and dibromoaminated products were produced by this method