1-Fluoropyridinium tetrafluoroborate

Chemical Properties

off-white powder

Uses

1-Fluoropyridine tetrafluoroborate is a pyridine organic compound, which can be used as an intermediate in pharmaceutical synthesis.

General Description

1-Fluoropyridinium tetrafluoroborate (N-Fluoropyridinium tetrafluoroborate), an N-fluorinated compound, is an electrophilic fluorinating reagent (containing N and F double bond). Controlled potential electrolysis of 1-fluoropyridinium tetrafluoroborate has been reported to afford pyridine, 2-fluoropyridine and 2-acetamidopyridine.

Research

The products from the controlled potential electrolysis of 1-fluoropyridinium tetrafluoroborate were determined to be pyridine, 2-fluoropyridine, and 2-acetamidopyridine in yields. Loss of fluoride ion from the neutral radical in equilibrium with the dimer is believed to be the initial step in a multi-step mechanism, which results in the products observed from the controlled potential coulometry of 1-fluoropyridinium tetrafluoroborate. Catalytic fluorination/chlorination competition experiments of β-keto ester 5 were used to assess the relative fluorinating activity of various electrophilic NF reagents (containing an NF bond). SelectfluorTM ( F-TEDA; TEDA=triethylenediamine) reacts more than 100 times faster than 1-fluoropyridinium tetrafluoroborate[1-2].

References

[1] Edward W Oliver, Dennis H Evans. “Electrochemical studies of six NF electrophilic fluorinating reagents.” Journal of Electroanalytical Chemistry 474 1 (1999): Pages 1-8.
[2] P. Toullec. “Relative Electrophilic Fluorinating Power as Assayed by Competitive Catalytic Halogenation Reactions.” ChemInform 56 1 (2005).