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Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes
Electrophotochemistry has enabled arene C−H trifluoromethylation with the Langlois reagent CF(3)SO(2)Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant‐free approach for the generation of the CF(3) radical. The electrophotochemistry...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155051/ https://www.ncbi.nlm.nih.gov/pubmed/31875327 http://dx.doi.org/10.1002/chem.201905774 |
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author | Qiu, Youai Scheremetjew, Alexej Finger, Lars H. Ackermann, Lutz |
author_facet | Qiu, Youai Scheremetjew, Alexej Finger, Lars H. Ackermann, Lutz |
author_sort | Qiu, Youai |
collection | PubMed |
description | Electrophotochemistry has enabled arene C−H trifluoromethylation with the Langlois reagent CF(3)SO(2)Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant‐free approach for the generation of the CF(3) radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C−H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron‐rich and electron‐deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C−H trifluoromethylation was further achieved in flow with a modular electro‐flow‐cell equipped with an in‐operando monitoring unit for on‐line flow‐NMR spectroscopy, providing support for the single electron transfer processes. |
format | Online Article Text |
id | pubmed-7155051 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-71550512020-04-15 Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes Qiu, Youai Scheremetjew, Alexej Finger, Lars H. Ackermann, Lutz Chemistry Communications Electrophotochemistry has enabled arene C−H trifluoromethylation with the Langlois reagent CF(3)SO(2)Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant‐free approach for the generation of the CF(3) radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C−H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron‐rich and electron‐deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C−H trifluoromethylation was further achieved in flow with a modular electro‐flow‐cell equipped with an in‐operando monitoring unit for on‐line flow‐NMR spectroscopy, providing support for the single electron transfer processes. John Wiley and Sons Inc. 2020-02-19 2020-03-12 /pmc/articles/PMC7155051/ /pubmed/31875327 http://dx.doi.org/10.1002/chem.201905774 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Qiu, Youai Scheremetjew, Alexej Finger, Lars H. Ackermann, Lutz Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes |
title | Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes |
title_full | Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes |
title_fullStr | Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes |
title_full_unstemmed | Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes |
title_short | Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes |
title_sort | electrophotocatalytic undirected c−h trifluoromethylations of (het)arenes |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155051/ https://www.ncbi.nlm.nih.gov/pubmed/31875327 http://dx.doi.org/10.1002/chem.201905774 |
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