Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Jenks, Tyler C., Bailey, Matthew D., Hovey, Jessica L., Fernando, Shanilke, Basnayake, Gihan, Cross, Michael E., Li, Wen, Allen, Matthew J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
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
_version_ 1783312920792268800
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
title_full First use of a divalent lanthanide for visible-light-promoted photoredox catalysis
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
title_short First use of a divalent lanthanide for visible-light-promoted photoredox catalysis
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
work_keys_str_mv AT jenkstylerc firstuseofadivalentlanthanideforvisiblelightpromotedphotoredoxcatalysis
AT baileymatthewd firstuseofadivalentlanthanideforvisiblelightpromotedphotoredoxcatalysis
AT hoveyjessical firstuseofadivalentlanthanideforvisiblelightpromotedphotoredoxcatalysis
AT fernandoshanilke firstuseofadivalentlanthanideforvisiblelightpromotedphotoredoxcatalysis
AT basnayakegihan firstuseofadivalentlanthanideforvisiblelightpromotedphotoredoxcatalysis
AT crossmichaele firstuseofadivalentlanthanideforvisiblelightpromotedphotoredoxcatalysis
AT liwen firstuseofadivalentlanthanideforvisiblelightpromotedphotoredoxcatalysis
AT allenmatthewj firstuseofadivalentlanthanideforvisiblelightpromotedphotoredoxcatalysis