title: Aminodifluorosulfinium salts: selective fluorination reagents with enhanced thermal stability and ease of handling.
abstract: Diethylaminodifluorosulfinium tetrafluoroborate (XtalFluor-E) and morpholinodifluorosulfinium tetrafluoroborate (XtalFluor-M) are crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues. These reagents can be prepared in a safer and more cost-efficient manner by avoiding the laborious and hazardous distillation of dialkylaminosulfur trifluorides. Unlike DAST, Deoxo-Fluor, and Fluolead, XtalFluor reagents do not generate highly corrosive free-HF and therefore can be used in standard borosilicate vessels. When used in conjunction with promoters such as Et(3)N.3HF, Et(3)N.2HF, or DBU, XtalFluor reagents effectively convert alcohols to alkyl fluorides and carbonyls to gem-difluorides. These reagents are typically more selective than DAST and Deoxo-Fluor and exhibit superior performance by providing significantly less elimination side products.
authors.affiliation: OmegaChem Inc., 480 Rue Perreault, St-Romuald (Qc) G6W 7V6, Canada.
authors.forename: Alexandre
authors.initials: A
authors.lastname: L'heureux
authors.forename: Francis
authors.initials: F
authors.lastname: Beaulieu
authors.forename: Christopher
authors.initials: C
authors.lastname: Bennett
authors.forename: David R
authors.initials: DR
authors.lastname: Bill
authors.forename: Simon
authors.initials: S
authors.lastname: Clayton
authors.forename: François
authors.initials: F
authors.lastname: Laflamme
authors.forename: Mahmoud
authors.initials: M
authors.lastname: Mirmehrabi
authors.forename: Sam
authors.initials: S
authors.lastname: Tadayon
authors.forename: David
authors.initials: D
authors.lastname: Tovell
authors.forename: Michel
authors.initials: M
authors.lastname: Couturier
mesh_terms: D001881:Borates / Q000138:chemical synthesis / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D012492:Salts / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013696:Temperature
chemical_list: D001881:Borates; D006845:Hydrocarbons, Fluorinated; D009025:Morpholines; D012492:Salts; D013457:Sulfur Compounds; C551695:diethylaminodifluorosulfinium tetrafluoroborate; C551696:morpholinodifluorosulfinium tetrafluoroborate
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