N-fluoropyridinium triflate and its derivatives: Useful fluorinating agents

Fluorine Compounds, Organic

“…Sulfur tetrafluoride and the following compounds can be used for the controlled introduction of fluorine into organic compounds: Dialkylaminosulfur(IV) fluorides (R 2 NSF 3 ) [44][45][46], arylsulfurtrifluorides [47], fluoroalkylamines (e.g., 2-chloro-1,1,2-trifluoroethyldiethylamine or 1,1,2,3,3,3-hexafluoropropyldiethylamine), tetra-n-butylammonium fluoride, amine hydrofluorides, nitrosyl fluoride, perchloryl fluoride, fluoroxyfluoroalkanes (e.g., CF 3 OF) [48], xenon difluoride [49], CH 3 COOF [50], N-fluoropyridinium salts [51], N-fluorosulfonimides [52], and Selectfluor [53]. They are of commercial value for the fluorination of complex organic compounds, such as pharmaceuticals.…”

Microwave fluorination: a novel, rapid approach to fluorination with Selectfluor®

“…It is perhaps not surprising that reactions with N-fluoropyridinium triflate (8) and N-fluoro-2,4,6-trimethylpyridinium triflate (9) were poor yielding as Umemoto et al [17] reported that such reagents were inferior to methoxy-carbonyl substituted examples, or their bipyridinium counterparts like (7) [16]. However, their reactivity under microwave conditions was unknown.…”

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

“…The use of a transition metal catalyst or mediator can enable more selective arene fluorination, using milder conditions and less reactive electrophilic fluorinating reagents such as Selectfluor (F-TEDA-BF 4 ) [83,139], N-fluorobenzenesulfonimide (NFBS) [12,[140][141][142][143][144], and N-fluoropyridinium salts [3,[84][85][86][87][145][146][147][148][149][150]. Additionally, transition metal-mediated or metal-catalyzed electrophilic arene fluorination can occur through a range of mechanisms, including one-and two-electron pathways.…”