Deoxygenative Fluorination of Phosphine Oxides: A General Route to Fluorinated Organophosphorus(V) Compounds and Beyond
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Date
2020-12-07Type
- Journal Article
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Cited 12 times in
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Cited 13 times in
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Abstract
Fluorinated organophosphorus(V) compounds are a very versatile class of compounds, but the synthetic methods available to make them bear the disadvantages of 1) occasional handling of toxic or pyrophoric P(III)starting materials and 2) a dependence on hazardous fluorinating reagents such as XeF2. Herein, we present a simple solution and introduce a deoxygenative fluorination (DOF) approach that utilizes easy-to-handle phosphine oxides as starting materials and effectively replaces harsh fluorinating reagents by a combination of oxalyl chloride and potassium fluoride. The reaction has proven to be general, as R3PF2, R2PF3, and RPF(4)compounds (as well as various cations and anions derived from these) are accessible in good yields and on up to a multi-gram scale. DFT calculations were used to bolster our observations. Notably, the discovery of this new method led to a convenient synthesis of 1) new difluorophosphonium ions, 2) hexafluorophosphate salts, and 3) fluorinated antimony- and arsenic- compounds. Show more
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publishedExternal links
Journal / series
Angewandte Chemie. International EditionVolume
Pages / Article No.
Publisher
WileySubject
deoxyfluorination; fluorine; fluorophosphates; phosphonium fluorides; phosphorusOrganisational unit
03447 - Grützmacher, Hansjörg / Grützmacher, Hansjörg
03363 - Togni, Antonio (emeritus) / Togni, Antonio (emeritus)
02024 - Small Molecule Crystallography Center
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Show all metadata
Citations
Cited 12 times in
Web of Science
Cited 13 times in
Scopus
ETH Bibliography
yes
Altmetrics