Journal article
Iron‐Catalyzed Halogen Exchange of Trifluoromethyl Arenes
Chemistry : a European journal, Vol.27(42), pp.10839-10843
06/17/2021
DOI: 10.1002/chem.202101324
PMID: 34137084
Abstract
The facile production of ArCF2X and ArCX3 from ArCF3 using catalytic iron(III)halides is reported, which constitutes the first iron-catalyzed halogen exchange for non-aromatic C−F bonds. Theoretical calculations suggest direct activation of C−F bonds by iron coordination. ArCX3 and ArCF2X products of the reaction are synthetically valuable due to their diversification potential. In particular, chloro- and bromodifluoromethyl arenes (ArCF2Cl, ArCF2Br respectively) provide access to a myriad of difluoromethyl arene derivatives (ArCF2R). To optimize for mono-halogen exchange, a statistical method called Design of Experiments was used. Optimized parameters were successfully applied to electron rich and electron deficient aromatic substrates, and to the late stage diversification of flufenoxuron, a commercial insecticide. These methods are highly practical, being run at convenient temperatures and using inexpensive common reagents.
Details
- Title: Subtitle
- Iron‐Catalyzed Halogen Exchange of Trifluoromethyl Arenes
- Creators
- Andreas Dorian - Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 CanadaEmily J Landgreen - Department of Chemistry University of Iowa Iowa City Iowa 52242 USAHayley R Petras - Department of Chemistry University of Iowa Iowa City Iowa 52242 USAJames J Shepherd - Department of Chemistry University of Iowa Iowa City Iowa 52242 USAFlorence J Williams - Department of Chemistry University of Iowa Iowa City Iowa 52242 USA
- Resource Type
- Journal article
- Publication Details
- Chemistry : a European journal, Vol.27(42), pp.10839-10843
- DOI
- 10.1002/chem.202101324
- PMID
- 34137084
- ISSN
- 0947-6539
- eISSN
- 1521-3765
- Grant note
- DOI: 10.13039/501100000038, name: Natural Sciences and Engineering Research Council of Canada, award: RGPIN-2016-04843, RGPIN-2019-04481; DOI: 10.13039/100006770, name: American Chemical Society Petroleum Research Fund, award: PRF 59191-ND1
- Language
- English
- Date published
- 06/17/2021
- Academic Unit
- Iowa Neuroscience Institute; Chemistry
- Record Identifier
- 9984090792802771
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