Journal article
Making the SF5 Group More Accessible: A Gas-Reagent-Free Approach to Aryl Tetrafluoro-λ6 -sulfanyl Chlorides.
- Pitts CR Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 2, 8093, Zürich, Switzerland.
- Bornemann D Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 2, 8093, Zürich, Switzerland.
- Liebing P Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 2, 8093, Zürich, Switzerland.
- Santschi N Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 2, 8093, Zürich, Switzerland.
- Togni A Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 2, 8093, Zürich, Switzerland.
- 2018-11-15
Published in:
- Angewandte Chemie (International ed. in English). - 2019
gas-reagent-free
inorganic fluorine chemistry
oxidative fluorination
pentafluorosulfanyl group
trichloroisocyanuric acid
English
Modern pentafluorosulfanyl (SF5 ) chemistry has an Achilles heel: synthetic accessibility. Herein, we present the first approach to aryl-SF4 Cl compounds (key intermediates in state-of-the-art aryl-SF5 synthesis) that overcomes the reliance on hazardous fluorinating reagents and/or gas reagents (e.g. Cl2 ) by employing easy-to-handle trichloroisocyanuric acid, potassium fluoride, and catalytic amounts of acid. These simple, mild conditions allow direct access to aryl-SF4 Cl intermediates that either have not been or cannot be demonstrated using previous methods. Furthermore, the same approach provides access to aryl-SF3 and aryl-SeF3 compounds, which extend the applications of this chemistry beyond arene SF5 -functionalization, and demonstrate its ability to address a more general oxidative fluorination problem.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1002/anie.201812356
- PMID 30427571
- Persistent URL
- https://sonar.ch/global/documents/15509
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