Issue 44, 2019

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, 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.

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

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
02 Jul 2019
Accepted
01 Aug 2019
First published
13 Aug 2019
This article is Open Access
Creative Commons BY license

RSC Adv., 2019,9, 25368-25376

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

M. Jakubczyk, S. Mkrtchyan, I. D. Madura, P. H. Marek and V. O. Iaroshenko, RSC Adv., 2019, 9, 25368 DOI: 10.1039/C9RA05004C

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