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F-TEDA-BF4

F-TEDA-BF₄ is a reagent in chemistry used as a fluorine donor. It is a DABCO derivative with full name 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) and discovered in 1992 ^[1]

The compound is synthesized by reaction of diazabicyclo[2.2.2]octane (DABCO) with dichloromethane, followed by ion exchange with sodium tetrafluoroborate (replacing the chlorine counterion for the tetrafluoroborate one) and finally reaction with elemental fluorine and sodium tetrafluoroborane. In contrast to hazardous fluorine this reagent is safe to use. It is listed as a superelectrophile.

Additional recommended knowledge

Fluorination of alkenes, alkynes. Formation of Fluorocarbons.
Organic oxidation. Oxidation of alcohols and phenols
Electrophilic iodination. In this reaction type F-TEDA-BF₄ activates the I-I bond for electrophilic addition.

References

^ 1-Alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts: a novel family of electrophilic fluorinating agents R. Eric Banks, Suad N. Mohialdin-Khaffaf, G. Sankar Lal, Iqbal Sharif and Robert G. Syvret, J. Chem. Soc., Chem. Commun., 1992, 595 doi:10.1039/C39920000595
^ Selectfluor (F-TEDA-BF4) C₇H₁₄B₂ClF₉N₂ Laxmi Manral SYNLETT 2006, No. 5, pp 0807–080 doi:10.1055/s-2006-933124 10.1055/s-2006-933124
^ SelectfluorTM F-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Chemistry Stojan Stavbera and Marko Zupana Acta Chim. Slov. 2005, 52, 13–26 http://acta.chem-soc.si/52/52-1-13.pdf