Copper-catalyzed direct C–H arylselenation of 4-nitro-pyrazoles and other heterocycles with selenium powder and aryl iodides. Access to unsymmetrical heteroaryl selenides. Issue 44 (13th August 2019)

• Record Type: Journal Article
• Authors: Jakubczyk, Michał; Mkrtchyan, Satenik; Madura, Izabela D.; Marek, Paulina H.; Iaroshenko, Viktor O.
• Is Part Of: RSC advances. Volume 9:Issue 44(2019)
• Page Start: 25368
• Page End: 25376
• Publication Date: 2019-08-13
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9ra05004c
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : In this work, we elaborated a general and straightforward method which permits the rapid assembly of unsymmetrical heteroaryl-aryl selenides containing 4-nitropyrazole, 4-nitroimidazole and a few other heterocyclic scaffolds. 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 4 H -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.