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Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light
In this study, direct C–H photoarylation of pyrazine with aryldiazonium salts under visible-light irradiation (blue-LEDs) is described, and additional examples including photoarylations of pyrimidine and pyridazine are also covered. The corresponding aryl-diazines were prepared in yields up to 84% o...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9056432/ https://www.ncbi.nlm.nih.gov/pubmed/35520669 http://dx.doi.org/10.1039/d0ra06876d |
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author | Silva, Rodrigo C. Villela, Lucas F. Brocksom, Timothy J. de Oliveira, Kleber T. |
author_facet | Silva, Rodrigo C. Villela, Lucas F. Brocksom, Timothy J. de Oliveira, Kleber T. |
author_sort | Silva, Rodrigo C. |
collection | PubMed |
description | In this study, direct C–H photoarylation of pyrazine with aryldiazonium salts under visible-light irradiation (blue-LEDs) is described, and additional examples including photoarylations of pyrimidine and pyridazine are also covered. The corresponding aryl-diazines were prepared in yields up to 84% only by mixing and irradiating the reaction with no need for an additional photocatalyst. We demonstrate the efficacy of this protocol by the scope with electron-donor, -neutral, and -withdrawing groups attached at the ortho, meta, and para positions of the aryldiazonium salts; the results are better than those reported for ruthenium-complex mediated photoarylations. Additionally, we demonstrate the robustness of this methodology with a 5 mmol scaled-up experiment. Mechanistic studies were carried out giving support to the proposal of a photocatalyzed approach by an electron donor–acceptor (EDA) complex, also highlighting the crucial role that solvents play in the formation of the EDA complex. |
format | Online Article Text |
id | pubmed-9056432 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90564322022-05-04 Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light Silva, Rodrigo C. Villela, Lucas F. Brocksom, Timothy J. de Oliveira, Kleber T. RSC Adv Chemistry In this study, direct C–H photoarylation of pyrazine with aryldiazonium salts under visible-light irradiation (blue-LEDs) is described, and additional examples including photoarylations of pyrimidine and pyridazine are also covered. The corresponding aryl-diazines were prepared in yields up to 84% only by mixing and irradiating the reaction with no need for an additional photocatalyst. We demonstrate the efficacy of this protocol by the scope with electron-donor, -neutral, and -withdrawing groups attached at the ortho, meta, and para positions of the aryldiazonium salts; the results are better than those reported for ruthenium-complex mediated photoarylations. Additionally, we demonstrate the robustness of this methodology with a 5 mmol scaled-up experiment. Mechanistic studies were carried out giving support to the proposal of a photocatalyzed approach by an electron donor–acceptor (EDA) complex, also highlighting the crucial role that solvents play in the formation of the EDA complex. The Royal Society of Chemistry 2020-08-21 /pmc/articles/PMC9056432/ /pubmed/35520669 http://dx.doi.org/10.1039/d0ra06876d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Silva, Rodrigo C. Villela, Lucas F. Brocksom, Timothy J. de Oliveira, Kleber T. Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light |
title | Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light |
title_full | Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light |
title_fullStr | Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light |
title_full_unstemmed | Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light |
title_short | Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light |
title_sort | direct c–h photoarylation of diazines using aryldiazonium salts and visible-light |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9056432/ https://www.ncbi.nlm.nih.gov/pubmed/35520669 http://dx.doi.org/10.1039/d0ra06876d |
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