Copper-catalyzed direct C–H arylselenation of 4-nitro-pyrazoles and other heterocycles with selenium powder and aryl iodides. Access to unsymmetrical heteroaryl selenides

Abstract

A one-pot, Cu-catalyzed direct C-H arylselenation protocol using elemental Se and aryl iodides was developed for nitro-substituted, <i>N</i>-alkylated pyrazoles, imidazoles and other heterocycles including 4<i>H</i>-chromen-4-one. This general and concise method allows one to obtain a large number of unsymmetrical heteroaryl selenides bearing a variety of substituents. The presence of the nitro group was confirmed to be essential for the C-H activation and can also be used for further functionalisation and manipulation. Several examples of heteroannulated benzoselenazines were also synthesized using the developed synthetic protocol.