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Palladium-catalysed electrophilic aromatic C–H fluorination

MPS-Authors
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Yamamoto,  Kumiko
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Department of Chemistry and Chemical Biology, Harvard University;

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Li,  Jiakun
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Garber,  Jeffrey A. O.
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Department of Chemistry and Chemical Biology, Harvard University;

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Rolfes,  Julian David
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Department of Chemistry and Chemical Biology, Harvard University;

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Boursalian,  Gregory
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Department of Chemistry and Chemical Biology, Harvard University;

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van Gastel,  Maurice
Research Group van Gastel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Neese,  Frank
Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ritter,  Tobias
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Yamamoto, K., Li, J., Garber, J. A. O., Rolfes, J. D., Boursalian, G., Borghs, J. C., et al. (2018). Palladium-catalysed electrophilic aromatic C–H fluorination. Nature, 554, 511-514. doi:10.1038/nature25749.


Cite as: https://hdl.handle.net/21.11116/0000-0000-B0E2-9
Abstract
Aryl fluorides are widely used in the pharmaceutical and agrochemical industries1,2, and recent advances have enabled their synthesis through the conversion of various functional groups. However, there is a lack of general methods for direct aromatic carbon–hydrogen (C–H) fluorination3. Conventional methods require the use of either strong fluorinating reagents, which are often unselective and difficult to handle, such as elemental fluorine, or less reactive reagents that attack only the most activated arenes, which reduces the substrate scope. A method for the direct fluorination of aromatic C–H bonds could facilitate access to fluorinated derivatives of functional molecules that would otherwise be difficult to produce. For example, drug candidates with improved properties, such as increased metabolic stability or better blood–brain-barrier penetration, may become available. Here we describe an approach to catalysis and the resulting development of an undirected, palladium-catalysed method for aromatic C–H fluorination using mild electrophilic fluorinating reagents. The reaction involves a mode of catalysis that is unusual in aromatic C–H functionalization because no organometallic intermediate is formed; instead, a reactive transition-metal-fluoride electrophile is generated catalytically for the fluorination of arenes that do not otherwise react with mild fluorinating reagents. The scope and functional-group tolerance of this reaction could provide access to functional fluorinated molecules in pharmaceutical and agrochemical development that would otherwise not be readily accessible.