ChemInform Abstract: Exploratory Study of the Reaction of Bis(2-methoxyethyl)aminosulfur Trifluoride (Deoxofluor Reagent) with Diaryl Sulfoxides: Novel Routes to Ar2SF2 and Ar2SF(OTf) via Sulfoxide Activation

Autor:	G. I. Borodkin, Kenneth K. Laali
Rok vydání:	2010
Předmět:	chemistry.chemical_compound Trifluoride chemistry Sulfonium Reagent Pyridine Halogenation Sulfoxide Protonation General Medicine Medicinal chemistry Trifluoromethanesulfonate
Zdroj:	ChemInform. 33
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200242102
Popis:	Neither bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor™ reagent) nor HF/pyridine alone can fluorinate diaryl sulfoxides. S-fluorination can be effected by activating the sulfoxide via protonation with HF/pyridine (70:30) to form sulfoxonium ions in equilibrium which are then S-fluorinated in situ with Deoxofluor™ to give Ar2SF2 compounds. Conversions depend strongly on steric factors and the reactions require the use of excess Deoxofluor™ and HF/pyridine. NMR data for the resulting diarylsulfur difluorides are gathered and discussed. Sulfoxide activation via diaryl (trifloxy) sulfonium triflate generated in situ from Ar2SO with triflic anhydride at low temperature represents another strategy for S-fluorination with Deoxofluor™ to generate Ar2S(OTf)F.
Databáze:	OpenAIRE
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