Phosphonium SF 5 - Salts Derived from Sulfur Hexafluoride as Deoxyfluorination Reagents

Sulfur based deoxyfluorination reagents are usually derived from the corrosive gas SF . Herein, we report the synthesis and properties of an easily accessible phosphonium salt [(tmg) PF] SF (1) which was obtained from the reaction of sulfur hexafluoride (SF ) with tris(tetramethylguanidinyl)phosphin...

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Published inChemistry : a European journal Vol. 30; no. 56; p. e202402028
Main Authors Röthel, Maike B, Schöler, Andreas, Buß, Florenz, Löwe, Pawel, Dielmann, Fabian
Format Journal Article
LanguageEnglish
Published Germany 08.10.2024
Subjects
deoxyfluorination
sulfur hexafluoride
fluorinations
fluorine
phosphorus
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Summary:Sulfur based deoxyfluorination reagents are usually derived from the corrosive gas SF . Herein, we report the synthesis and properties of an easily accessible phosphonium salt [(tmg) PF] SF (1) which was obtained from the reaction of sulfur hexafluoride (SF ) with tris(tetramethylguanidinyl)phosphine. The performance of this crystalline SF salt as a reagent in deoxyfluorination reactions was investigated together with a second SF salt [(R ) PF] SF (2) containing bulky substituents (R =1,3-di-tert-butylimidazolidin-2-ylidenamino). Both reagents proved to be effective for the deoxyfluorination of various functional groups including alcohols, anhydrides, and amides.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202402028