1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

• Catalog: OFC172090265
• CAS: 172090-26-5
• Category: Other Fluorinated Group Introducing Agents
• Synonyms: Accufluor; Accufluor NFTh

• InChI: InChI=1S/C6H13FN2O.2BF4/c7-8-1-4-9(10,5-2-8)6-3-8;2*2-1(3,4)5/h10H,1-6H2;;/q+2;2*-1
• InChI Key: DRMMNFGYCLJZKD-UHFFFAOYSA-N
• Canonical SMILES: F[B-](F)(F)F.F[B-](F)(F)F.O[N+]12CC[N+](F)(CC1)CC2

• Molecular Formula: C6H13B2F9N2O
• Molecular Weight: 321.789
• Melting Point: 336-338 °C

• Exact Mass: 322.107

Case Study

1-Fluoro-4-Hydroxy-1,4-Diazoniabicyclo[2.2.2]Octane Bis(tetrafluoroborate) as an Electrophilic Fluorinating Agent for Fluorination Reactions

Andrew J. Poss, et al. Tetrahedron Letters, 1999, 40(14), 2673-2676.

1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (NFTh) can be used as an electrophilic fluorinating agent for the fluorination of aryl rings, olefins, dienyl alcohol acetates, and enol ethers. It is capable of introducing fluorine into the reactive site of an aromatic ring, a stable carbon-carbon double bond, or an electron-rich olefin (e.g., a dienol acetate or a silyl enol ether).
Treatment of electron-rich aromatic compounds with NFTh in acetonitrile gives the corresponding fluoroaromatic compounds in high yields. (Fig. 1)
Fluorine can be selectively introduced into the 6-position of the steroid by using a dienol derivative. (Fig. 2)
We found that enol acetates, enol ethers, and trimethylsilyl enol ethers can also react effectively with NFTh in acetonitrile to produce a-fluoro ketones. (Fig. 3)
NFTh is able to introduce fluorine on a stable carbon-carbon double bond to produce a fluorinated ether or alcohol. (Fig. 4)
In the presence of Lewis acid, NFTh can be used to convert reactive methylene compounds to their corresponding mono- or difluorinated derivatives. Monofluorodiketones predominate when the fluorinating agent is limited to one equivalent and imidazole is used as the amine component. Bifluorination is accomplished with an excess of NFTh and trimethylpyridine as a concomitant base. (Fig. 5)