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

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...

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Published inJournal of the American Chemical Society Vol. 137; no. 41; pp. 13433 - 13438
Main Authors Sather, Aaron C, Lee, Hong Geun, De La Rosa, Valentina Y, Yang, Yang, Müller, Peter, Buchwald, Stephen L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.10.2015
Amer Chemical Soc
Subjects
Bromides - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Fluorine - chemistry
Ligands
Models, Molecular
Palladium - chemistry
Physical Sciences
Science & Technology
Temperature
MEDICINAL CHEMISTRY
AROMATIC FLUORINATION
PALLADIUM
NUCLEOPHILIC FLUORINATION
F REDUCTIVE ELIMINATION
COMPLEXES
BOND FORMATION
MIYAURA COUPLING PROCESSES
LATE-STAGE FLUORINATION
FLUORIDE
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Summary: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.
Bibliography:NIH RePORTER
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SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b09308