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  Photoredox catalysis with aryl sulfonium salts enables site-selective late-stage fluorination

Li, J., Chen, J., Sang, R., Ham, W.-S., Plutschack, M. B., Berger, F., et al. (2020). Photoredox catalysis with aryl sulfonium salts enables site-selective late-stage fluorination. Nature Chemistry, 12(1), 56-62. doi:10.1038/s41557-019-0353-3.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-6939-6 Version Permalink: http://hdl.handle.net/21.11116/0000-0005-693A-5
Genre: Journal Article

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 Creators:
Li, Jiakun1, Author              
Chen, Junting1, Author              
Sang, Ruocheng1, Author              
Ham, Won-Seok1, Author              
Plutschack, Matthew B.1, Author              
Berger, Florian1, Author              
Chabbra, Sonia2, Author
Schnegg, Alexander2, Author
Genicot, Christophe3, Author
Ritter, Tobias1, Author              
Affiliations:
1Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040308              
2Max-Planck-Institut für Chemische Energiekonversion, Mülheim an der Ruhr, Germany, ou_persistent22              
3Global Chemistry, UCB Biopharma SPRL, Braine-l’Alleud, Belgium, ou_persistent22              

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 Abstract: Photoredox catalysis, especially in combination with transition metal catalysis, can produce redox states of transition metal catalysts to facilitate challenging bond formations that are not readily accessible in conventional redox catalysis. For arene functionalization, metallophotoredox catalysis has successfully made use of the same leaving groups as those valuable in conventional cross-coupling catalysis, such as bromide. Yet the redox potentials of common photoredox catalysts are not sufficient to reduce most aryl bromides, so synthetically useful aryl radicals are often not directly available. Therefore, the development of a distinct leaving group more appropriately matched in redox potential could enable new reactivity manifolds for metallophotoredox catalysis, especially if arylcopper(iii) complexes are accessible, from which the most challenging bond-forming reactions can occur. Here we show the conceptual advantages of aryl thianthrenium salts for metallophotoredox catalysis, and their utility in site-selective late-stage aromatic fluorination.

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Language(s): eng - English
 Dates: 2019-04-242019-09-172019-11-252020-01-01
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1038/s41557-019-0353-3
 Degree: -

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Title: Nature Chemistry
  Abbreviation : Nat. Chem.
Source Genre: Journal
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Publ. Info: London, UK : Nature Publishing Group
Pages: - Volume / Issue: 12 (1) Sequence Number: - Start / End Page: 56 - 62 Identifier: ISSN: 1755-4330
CoNE: https://pure.mpg.de/cone/journals/resource/1755-4330