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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...

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Autores principales: Qiu, Youai, Scheremetjew, Alexej, Finger, Lars H., Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
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.
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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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