133745-75-2 N-Fluorobenzenesulfonimide

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Stable, non-hygroscopic, glass-compatible mild electrophilic fluorinating agent, very soluble in acetonitrile, dichloromethane or THF, less soluble in toluene. Fluorinates aromatics, enolates, azaenolates and carbanions in high yield: Synlett, 187, 395 (1991); Tetrahedron Lett., 32, 1631 (1991); for diastereoselective fluorination of Li enolates of chiral carboximides, see: Tetrahedron Lett., 33, 1153 (1992). Asymmteric fluorinations have been effected in the presence of a Pd-BINAP catalyst system at room temperature in an ionic liquid: Org. Lett., 5, 3225 (2003).
For directed fluorination of ortho-lithiated aromatics, see: Tetrahedron Lett., 35, 3465 (1994); ɑɑ-difluorination of benzylic phosphonate anions: Tetrahedron, 54, 1691 (1998); andof benzylic nitriles, tetrazoles and sulfonates: J. Org. Chem., 63, 8052 (1998).
For a review of electrophilic N-F fluorinating agents, see: Chem. Rev., 96, 1737 (1996).