Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling

[Image: see text] Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst (t)BuBrettPhos Pd G3 and Cs(2)CO(3) in toluene. This Pd-catalyzed coupling features a short reaction time, excellent...

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Autores principales: Szpera, Robert, Isenegger, Patrick G., Ghosez, Maxime, Straathof, Natan J. W., Cookson, Rosa, Blakemore, David C., Richardson, Paul, Gouverneur, Véronique
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7458480/
https://www.ncbi.nlm.nih.gov/pubmed/32806200
http://dx.doi.org/10.1021/acs.orglett.0c02347
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author Szpera, Robert
Isenegger, Patrick G.
Ghosez, Maxime
Straathof, Natan J. W.
Cookson, Rosa
Blakemore, David C.
Richardson, Paul
Gouverneur, Véronique
author_facet Szpera, Robert
Isenegger, Patrick G.
Ghosez, Maxime
Straathof, Natan J. W.
Cookson, Rosa
Blakemore, David C.
Richardson, Paul
Gouverneur, Véronique
author_sort Szpera, Robert
collection PubMed
description [Image: see text] Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst (t)BuBrettPhos Pd G3 and Cs(2)CO(3) in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and -poor (hetero)arenes. The method provides access to (18)F-labeled trifluoroethyl ethers by cross-coupling with [(18)F]trifluoroethanol.
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spelling pubmed-74584802020-09-01 Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling Szpera, Robert Isenegger, Patrick G. Ghosez, Maxime Straathof, Natan J. W. Cookson, Rosa Blakemore, David C. Richardson, Paul Gouverneur, Véronique Org Lett [Image: see text] Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst (t)BuBrettPhos Pd G3 and Cs(2)CO(3) in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and -poor (hetero)arenes. The method provides access to (18)F-labeled trifluoroethyl ethers by cross-coupling with [(18)F]trifluoroethanol. American Chemical Society 2020-08-04 2020-08-21 /pmc/articles/PMC7458480/ /pubmed/32806200 http://dx.doi.org/10.1021/acs.orglett.0c02347 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Szpera, Robert
Isenegger, Patrick G.
Ghosez, Maxime
Straathof, Natan J. W.
Cookson, Rosa
Blakemore, David C.
Richardson, Paul
Gouverneur, Véronique
Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling
title Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling
title_full Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling
title_fullStr Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling
title_full_unstemmed Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling
title_short Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling
title_sort synthesis of fluorinated alkyl aryl ethers by palladium-catalyzed c–o cross-coupling
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7458480/
https://www.ncbi.nlm.nih.gov/pubmed/32806200
http://dx.doi.org/10.1021/acs.orglett.0c02347
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