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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.
Hazard Statements: H302-H317-H318
Harmful if swallowed. May cause an allergic skin reaction. Causes serious eye damage.
Precautionary Statements: P261-P264b-P270-P272-P280-P301+P312-P302+P352-P305+P351+P338-P310-P330-P333+P313-P363-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant