C−H Fluoromethoxylation of Arenes by Photoredox Catalysis

Redox‐active N‐(fluoromethoxy)benzotriazoles were made accessible from fluoroacetic acid and hydroxybenzotriazoles via electrodecarboxylative coupling. After alkylation, they become effective monofluoromethoxylation reagents, enabling the photocatalytic C−H functionalization of arenes. Thus, irradia...

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Detalles Bibliográficos
Autores principales: Bertoli, Giulia, Martínez, Ángel Manu, Goebel, Jonas F., Belmonte, Debora, Sivendran, Nardana, Gooßen, Lukas J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107189/
https://www.ncbi.nlm.nih.gov/pubmed/36385731
http://dx.doi.org/10.1002/anie.202215920
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author Bertoli, Giulia
Martínez, Ángel Manu
Goebel, Jonas F.
Belmonte, Debora
Sivendran, Nardana
Gooßen, Lukas J.
author_facet Bertoli, Giulia
Martínez, Ángel Manu
Goebel, Jonas F.
Belmonte, Debora
Sivendran, Nardana
Gooßen, Lukas J.
author_sort Bertoli, Giulia
collection PubMed
description Redox‐active N‐(fluoromethoxy)benzotriazoles were made accessible from fluoroacetic acid and hydroxybenzotriazoles via electrodecarboxylative coupling. After alkylation, they become effective monofluoromethoxylation reagents, enabling the photocatalytic C−H functionalization of arenes. Thus, irradiation of 1‐(OCH(2)F)‐3‐Me‐6‐(CF(3))benzotriazolium triflate with blue LED light in the presence of [Ru(bpy)(3)(PF(6))(2)] promotes the synthesis of diversely functionalized aryl monofluoromethyl ethers. This method allows the late‐stage functionalization of biologically relevant structures without relying on ecologically problematic halofluorocarbons.
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spelling pubmed-101071892023-04-18 C−H Fluoromethoxylation of Arenes by Photoredox Catalysis Bertoli, Giulia Martínez, Ángel Manu Goebel, Jonas F. Belmonte, Debora Sivendran, Nardana Gooßen, Lukas J. Angew Chem Int Ed Engl Communications Redox‐active N‐(fluoromethoxy)benzotriazoles were made accessible from fluoroacetic acid and hydroxybenzotriazoles via electrodecarboxylative coupling. After alkylation, they become effective monofluoromethoxylation reagents, enabling the photocatalytic C−H functionalization of arenes. Thus, irradiation of 1‐(OCH(2)F)‐3‐Me‐6‐(CF(3))benzotriazolium triflate with blue LED light in the presence of [Ru(bpy)(3)(PF(6))(2)] promotes the synthesis of diversely functionalized aryl monofluoromethyl ethers. This method allows the late‐stage functionalization of biologically relevant structures without relying on ecologically problematic halofluorocarbons. John Wiley and Sons Inc. 2022-12-27 2023-01-26 /pmc/articles/PMC10107189/ /pubmed/36385731 http://dx.doi.org/10.1002/anie.202215920 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Bertoli, Giulia
Martínez, Ángel Manu
Goebel, Jonas F.
Belmonte, Debora
Sivendran, Nardana
Gooßen, Lukas J.
C−H Fluoromethoxylation of Arenes by Photoredox Catalysis
title C−H Fluoromethoxylation of Arenes by Photoredox Catalysis
title_full C−H Fluoromethoxylation of Arenes by Photoredox Catalysis
title_fullStr C−H Fluoromethoxylation of Arenes by Photoredox Catalysis
title_full_unstemmed C−H Fluoromethoxylation of Arenes by Photoredox Catalysis
title_short C−H Fluoromethoxylation of Arenes by Photoredox Catalysis
title_sort c−h fluoromethoxylation of arenes by photoredox catalysis
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107189/
https://www.ncbi.nlm.nih.gov/pubmed/36385731
http://dx.doi.org/10.1002/anie.202215920
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