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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.

SUBMITTER: Jakubczyk M

PROVIDER: S-EPMC9070035 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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

Jakubczyk Michał M Mkrtchyan Satenik S Madura Izabela D ID Marek Paulina H PH Iaroshenko Viktor O VO Iaroshenko Viktor O VO

RSC advances 20190813 44

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 functional ...[more]

PMID: 35530113

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