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

Michał Jakubczyk; Satenik Mkrtchyan; Izabela D Madura; Paulina H Marek; Viktor O Iaroshenko

doi:10.1039/c9ra05004c

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

RSC Adv. 2019 Aug 13;9(44):25368-25376. doi: 10.1039/c9ra05004c.

Authors

Michał Jakubczyk¹, Satenik Mkrtchyan¹, Izabela D Madura², Paulina H Marek^{2

3}, Viktor O Iaroshenko¹

Affiliations

¹ Laboratory of Homogeneous Catalysis and Molecular Design at the Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences Sienkiewicza 112 PL-90-363 Łodź Poland iva108@gmail.com viktori@cbmm.lodz.pl.
² Department of Inorganic Chemistry, Faculty of Chemistry, Warsaw University of Technology Noakowskiego 3 00-664 Warsaw Poland.
³ Faculty of Chemistry, University of Warsaw Pasteura 1 02-093 Warsaw Poland.

Abstract

A one-pot, Cu-catalyzed direct C-H arylselenation protocol using elemental Se and aryl iodides was developed for nitro-substituted, N-alkylated pyrazoles, imidazoles and other heterocycles including 4H-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.