Chemical Properties
Off-white to light brown crystalline powder
Uses
Versatile fluorinating reagent used in the fluorination of aryls, enolates, carbanions, organolithiums, etc.
Uses
N-Fluorobenzenesulfonimide fluorinates aromatics, enolates, azaenolates and carbanions in high yield. It is used for diastereoselective fluorination of Li enolates of chiral carboximides, for directed fluorination of ortho-lithiated aromatics and for a review of electrophilic N-F fluorinating agents. Asymmteric fluorinations is effected in the presence of a Pd-BINAP catalyst system at room temperature in an ionic liquid. It is a reagent employed in a palladium-catalyzed enantioselective fluorination of t-butoxycarbonyl lactones and lactams. It is also used in the electrophilic difluorination of dihalopyridines with butyl lithium and in the direct conversion of alcohols to dibenzenesulfonamides with triphenylphosphine.
Application
N-Fluorobenzenesulfonimide is a mild electrophilic fluorinating reagent, that can also be used as a strong oxidant for the promotion of reductive elimination from transition metals.
General Description
N-Fluorobenzenesulfonimide (NFSi) is a commonly used electrophilic fluorinating agent in organic synthesis to introduce fluorine into neutral organic molecules. It is also used to fluorinate nucleophilic substrates such as reactive organometallic species and malonate anions.
NFSi can be synthesized by the reaction of benzenesulfonimide with fluorine.
Synthesis
There are two main methods for the production of N-fluorobenzenesulfonamide, the first Differding method, the specific preparation process is: diphenylsulfonimide dissolved in acetonitrile, add sodium fluoride, the mixture cooled down to -35 C, the volume ratio of 1:10 fluorine and nitrogen mixture into the 2h, nitrogen purging for 2h, filtration, evaporation, recrystallization process to obtain the white crystals, the yield is 74%.
The other one is Wanger method, the specific preparation process is as follows: diphenylsulfonamide sodium salt is dissolved in water/acetonitrile or pure water, and after cooling, fluorine and nitrogen mixture with V(F2):V(N2) = 1:10 is passed in, and after the reaction is finished, the reactor is purged with nitrogen, and after filtration, washing and drying, N-fluorosubstituted bisbenzenesulfonamide product is obtained, and the yield can reach 94% at the highest.
