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1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) is used as a reagent for electrophilic fluorination and also acts as a selective oxidizing agent. It is a highly effective and versatile source of electrophilic fluorine and also used in the synthesis of organofluorine.
SELECTFLUOR is a registered trademark of Air Products & Chemicals Inc.
Water- and organic-soluble reagent developed by R. E. Banks and co-workers for electrophilic fluorination of a variety of substrates under mild conditions: USP 5,086,178 (1992 to Air Products & Chemicals, Inc.); review: J. Fluorine Chem., 87, 1 (1998). In acetonitrile, activated aromatics can be fluorinated in good yield: J. Chem. Soc., Perkin 1., 2069 (1996). Less active substrates can be fluorinated in the presence of triflic acid: Israel J. Chem., 39, 207 (1999). In acetonitrile, vinylsilanes undergo fluorodesilylation to give vinyl fluorides with retention of configuration: Chem. Commun., 233 (2001).
Stabilized carbanions can be selectively mono- or difluorinated: J. Chem. Soc., Chem. Commun., 343 (1994); Tetrahedron, 51, 3587 (1995). Fluorinated steroids have been prepared from enol acetates or silyl enol ethers: J. Org. Chem., 58, 2791 (1993). 5-Fluoropyrimidine nucleosides can be obtained by treatment of protected nucleosides with the reagent in the presence of water or methanol, followed by elimination of the resulting fluorohydrin derivative: J. Org. Chem., 60, 7340 (1995).
For use in the synthesis of fluorinated carbohydrates by reaction with glycals, see: J. Am. Chem. Soc., 119, 11743 (1997); J. Org. Chem., 64, 5264 (1999).
For application to N-fluorination of amines, see: Chem. Commun., 1196 (2001). Review of mechanistic insight and applicatio ns of the rea
Laali, K. K.; Jamalian, A.; Zhao, C. Reaction of Selectfluor (F-TEDA-BF4) with chloromethylated-DABCO monocation salts (X= BF4, NTf2) and other nitrogen bases (Et3N; piperidine; basic ionic liquid); unexpected formation of symmetrical [N- H- N]+ trication salts. Tetrahedron Lett. 2014, 55 (49), 6643-6646.
Reddy, A. S.; Laali, K. K. Mild and selective α-fluorination of carbonyl compounds (ketones, 1, 3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF 4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Brønsted-acidic IL [PMIM (SO3H)/OTf] as promoter. Tetrahedron Lett. 2015, 56 (41), 5495-5499.
Gefahrenhinweise (EU): H302-H318-H317
Harmful if swallowed. Causes serious eye damage. May cause an allergic skin reaction.
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF SWALLOWED: Dispose of contents/container in accordance with local/regional/national/international regulations.