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First use of a divalent lanthanide for visible-light-promoted photoredox catalysis
We report the first catalytic use of a divalent lanthanide in visible-light-promoted bond-forming reactions. Our new precatalyst uses europium in the +2 oxidation state and is active in the presence of blue light from light-emitting diodes. The use of low-energy visible light reduces the occurrence...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5890796/ https://www.ncbi.nlm.nih.gov/pubmed/29675173 http://dx.doi.org/10.1039/c7sc02479g |
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author | Jenks, Tyler C. Bailey, Matthew D. Hovey, Jessica L. Fernando, Shanilke Basnayake, Gihan Cross, Michael E. Li, Wen Allen, Matthew J. |
author_facet | Jenks, Tyler C. Bailey, Matthew D. Hovey, Jessica L. Fernando, Shanilke Basnayake, Gihan Cross, Michael E. Li, Wen Allen, Matthew J. |
author_sort | Jenks, Tyler C. |
collection | PubMed |
description | We report the first catalytic use of a divalent lanthanide in visible-light-promoted bond-forming reactions. Our new precatalyst uses europium in the +2 oxidation state and is active in the presence of blue light from light-emitting diodes. The use of low-energy visible light reduces the occurrence of potential side reactions that might be induced by higher-energy UV light. The system described here uses zinc metal as a sacrificial reductant and is tolerant to wet, protic solvents. The catalyst can be made in situ from relatively inexpensive and air-stable EuCl(3)·6H(2)O, and the ligand can be synthesized in large quantities in two steps. With 0.5% loading of precatalyst, an average of 120 turnovers was observed in six hours for reductive coupling of benzyl chloride. We expect that the results will initiate the study of visible-light-promoted photoredox catalysis using divalent europium in a variety of reactions. |
format | Online Article Text |
id | pubmed-5890796 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-58907962018-04-19 First use of a divalent lanthanide for visible-light-promoted photoredox catalysis Jenks, Tyler C. Bailey, Matthew D. Hovey, Jessica L. Fernando, Shanilke Basnayake, Gihan Cross, Michael E. Li, Wen Allen, Matthew J. Chem Sci Chemistry We report the first catalytic use of a divalent lanthanide in visible-light-promoted bond-forming reactions. Our new precatalyst uses europium in the +2 oxidation state and is active in the presence of blue light from light-emitting diodes. The use of low-energy visible light reduces the occurrence of potential side reactions that might be induced by higher-energy UV light. The system described here uses zinc metal as a sacrificial reductant and is tolerant to wet, protic solvents. The catalyst can be made in situ from relatively inexpensive and air-stable EuCl(3)·6H(2)O, and the ligand can be synthesized in large quantities in two steps. With 0.5% loading of precatalyst, an average of 120 turnovers was observed in six hours for reductive coupling of benzyl chloride. We expect that the results will initiate the study of visible-light-promoted photoredox catalysis using divalent europium in a variety of reactions. Royal Society of Chemistry 2017-12-21 /pmc/articles/PMC5890796/ /pubmed/29675173 http://dx.doi.org/10.1039/c7sc02479g Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Jenks, Tyler C. Bailey, Matthew D. Hovey, Jessica L. Fernando, Shanilke Basnayake, Gihan Cross, Michael E. Li, Wen Allen, Matthew J. First use of a divalent lanthanide for visible-light-promoted photoredox catalysis |
title | First use of a divalent lanthanide for visible-light-promoted photoredox catalysis
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title_full | First use of a divalent lanthanide for visible-light-promoted photoredox catalysis
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title_fullStr | First use of a divalent lanthanide for visible-light-promoted photoredox catalysis
|
title_full_unstemmed | First use of a divalent lanthanide for visible-light-promoted photoredox catalysis
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title_short | First use of a divalent lanthanide for visible-light-promoted photoredox catalysis
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title_sort | first use of a divalent lanthanide for visible-light-promoted photoredox catalysis |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5890796/ https://www.ncbi.nlm.nih.gov/pubmed/29675173 http://dx.doi.org/10.1039/c7sc02479g |
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