Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 7, Pages 1950-1954Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812356
Keywords
gas-reagent-free; inorganic fluorine chemistry; oxidative fluorination; pentafluorosulfanyl group; trichloroisocyanuric acid
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Funding
- ETH Zurich
- ETH Postdoctoral Fellowship Program
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Modern pentafluorosulfanyl (SF5) chemistry has an Achilles heel: synthetic accessibility. Herein, we present the first approach to aryl-SF4Cl 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. Cl-2) by employing easy-to-handle trichloroisocyanuric acid, potassium fluoride, and catalytic amounts of acid. These simple, mild conditions allow direct access to aryl-SF4Cl 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.
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