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  Palladium-catalysed electrophilic aromatic C–H fluorination

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(7693), 511-514. doi:10.1038/nature25749.

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 Creators:
Yamamoto, Kumiko1, 2, Author              
Li, Jiakun1, Author              
Garber, Jeffrey A. O.1, 2, Author              
Rolfes, Julian David1, 2, Author              
Boursalian, Gregory1, 2, Author              
Borghs, Jannik C. 2, Author
Genicot, Christophe 3, Author
Jacq, Jérôme 3, Author
van Gastel, Maurice4, Author              
Neese, Frank5, Author              
Ritter, Tobias1, Author              
Affiliations:
1Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040308              
2Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA, ou_persistent22              
3Global Chemistry, UCB NewMedicines, UCB Biopharma, 1420 Braine-L’Alleud, Belgium, ou_persistent22              
4Research Group van Gastel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541713              
5Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541710              

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Free keywords: Homogeneous catalysis, Synthetic chemistry methodology, Palladium-propelled C-H fluorination
 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.

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Language(s): eng - English
 Dates: 2017-03-212017-12-172018-02-212018-02-22
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/nature25749
 Degree: -

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Title: Nature
  Abbreviation : Nature
Source Genre: Journal
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Publ. Info: London : Nature Publishing Group
Pages: - Volume / Issue: 554 (7693) Sequence Number: - Start / End Page: 511 - 514 Identifier: ISSN: 0028-0836
CoNE: https://pure.mpg.de/cone/journals/resource/954925427238