A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides

[Image: see text] A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can...

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Autores principales: Sather, Aaron C., Lee, Hong Geun, De La Rosa, Valentina Y., Yang, Yang, Müller, Peter, Buchwald, Stephen L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4721526/
https://www.ncbi.nlm.nih.gov/pubmed/26413908
http://dx.doi.org/10.1021/jacs.5b09308
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author Sather, Aaron C.
Lee, Hong Geun
De La Rosa, Valentina Y.
Yang, Yang
Müller, Peter
Buchwald, Stephen L.
author_facet Sather, Aaron C.
Lee, Hong Geun
De La Rosa, Valentina Y.
Yang, Yang
Müller, Peter
Buchwald, Stephen L.
author_sort Sather, Aaron C.
collection PubMed
description [Image: see text] A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.
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spelling pubmed-47215262016-09-28 A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides Sather, Aaron C. Lee, Hong Geun De La Rosa, Valentina Y. Yang, Yang Müller, Peter Buchwald, Stephen L. J Am Chem Soc [Image: see text] A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1. American Chemical Society 2015-09-28 2015-10-21 /pmc/articles/PMC4721526/ /pubmed/26413908 http://dx.doi.org/10.1021/jacs.5b09308 Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Sather, Aaron C.
Lee, Hong Geun
De La Rosa, Valentina Y.
Yang, Yang
Müller, Peter
Buchwald, Stephen L.
A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
title A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
title_full A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
title_fullStr A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
title_full_unstemmed A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
title_short A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
title_sort fluorinated ligand enables room-temperature and regioselective pd-catalyzed fluorination of aryl triflates and bromides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4721526/
https://www.ncbi.nlm.nih.gov/pubmed/26413908
http://dx.doi.org/10.1021/jacs.5b09308
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