Catalyst- and metal-free C(sp(2))–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature

In this paper, we report an eco-friendly approach for the C(sp(2))–H bond selenylation of imidazopyridines and other N-heteroarenes as well as simple arenes at ambient temperature. This new protocol consists of the reaction between (N-hetero)-arenes and the diorganyl-diselenides and trichloroisocyan...

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Autores principales: Neto, José S. S., Granja, Isis J. A., Scheide, Marcos R., Franco, Marcelo S., Moraes, Cassio A. O., Beatriz, Adilson, de Lima, Dênis P., Botteselle, Giancarlo V., Frizon, Tiago E. A., Saba, Sumbal, Rafique, Jamal, Braga, Antonio L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10471583/
https://www.ncbi.nlm.nih.gov/pubmed/37652946
http://dx.doi.org/10.1038/s41598-023-41430-9
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author Neto, José S. S.
Granja, Isis J. A.
Scheide, Marcos R.
Franco, Marcelo S.
Moraes, Cassio A. O.
Beatriz, Adilson
de Lima, Dênis P.
Botteselle, Giancarlo V.
Frizon, Tiago E. A.
Saba, Sumbal
Rafique, Jamal
Braga, Antonio L.
author_facet Neto, José S. S.
Granja, Isis J. A.
Scheide, Marcos R.
Franco, Marcelo S.
Moraes, Cassio A. O.
Beatriz, Adilson
de Lima, Dênis P.
Botteselle, Giancarlo V.
Frizon, Tiago E. A.
Saba, Sumbal
Rafique, Jamal
Braga, Antonio L.
author_sort Neto, José S. S.
collection PubMed
description In this paper, we report an eco-friendly approach for the C(sp(2))–H bond selenylation of imidazopyridines and other N-heteroarenes as well as simple arenes at ambient temperature. This new protocol consists of the reaction between (N-hetero)-arenes and the diorganyl-diselenides and trichloroisocyanuric acid (TCCA)-ethanol reagent system. In a short reaction time, the desired selenylated products were obtained regioselectively in good yields, with tolerance for a wide range of functional groups.
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spelling pubmed-104715832023-09-02 Catalyst- and metal-free C(sp(2))–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature Neto, José S. S. Granja, Isis J. A. Scheide, Marcos R. Franco, Marcelo S. Moraes, Cassio A. O. Beatriz, Adilson de Lima, Dênis P. Botteselle, Giancarlo V. Frizon, Tiago E. A. Saba, Sumbal Rafique, Jamal Braga, Antonio L. Sci Rep Article In this paper, we report an eco-friendly approach for the C(sp(2))–H bond selenylation of imidazopyridines and other N-heteroarenes as well as simple arenes at ambient temperature. This new protocol consists of the reaction between (N-hetero)-arenes and the diorganyl-diselenides and trichloroisocyanuric acid (TCCA)-ethanol reagent system. In a short reaction time, the desired selenylated products were obtained regioselectively in good yields, with tolerance for a wide range of functional groups. Nature Publishing Group UK 2023-08-31 /pmc/articles/PMC10471583/ /pubmed/37652946 http://dx.doi.org/10.1038/s41598-023-41430-9 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Neto, José S. S.
Granja, Isis J. A.
Scheide, Marcos R.
Franco, Marcelo S.
Moraes, Cassio A. O.
Beatriz, Adilson
de Lima, Dênis P.
Botteselle, Giancarlo V.
Frizon, Tiago E. A.
Saba, Sumbal
Rafique, Jamal
Braga, Antonio L.
Catalyst- and metal-free C(sp(2))–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature
title Catalyst- and metal-free C(sp(2))–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature
title_full Catalyst- and metal-free C(sp(2))–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature
title_fullStr Catalyst- and metal-free C(sp(2))–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature
title_full_unstemmed Catalyst- and metal-free C(sp(2))–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature
title_short Catalyst- and metal-free C(sp(2))–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature
title_sort catalyst- and metal-free c(sp(2))–h bond selenylation of (n-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10471583/
https://www.ncbi.nlm.nih.gov/pubmed/37652946
http://dx.doi.org/10.1038/s41598-023-41430-9
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