17715-70-7Relevant articles and documents
Acetyl Hypofluorite as a Taming Carrier of Elemental Fluorine for Novel Electrophilic Fluorination of Activated Aromatic Rings
Lerman, Ori,Tor, Yitzhak,Rozen, Shlomo
, p. 4629 - 4631 (1981)
The new fluorinating reagent CH3COOF, which is prepared in situ from F2, is used for electrophilic aromatic fluorinations of activated aromatic rings.
N-Halogeno compounds part 19: Electrophilic fluorinating agents of the multiple mono-N-fluoro class derived from nitrogen heterocycles
Banks, R. Eric,Besheesh, Mohamed K.,Mohialdin-Khaffaf, Suad N.,Sharif, Iqbal
, p. 157 - 161 (1997)
Bis(4-fluoro-1,4-diazoniabicyclo[2.2.2]oct-1-yl)-ethane and -propane tetratriflates (4, 5), and 1,1′-difluoro-4,4′-bipyridinium ditriflate (6) were prepared by solution-phase direct fluorination of bis(4-aza-1-azoniabicyclo[2.2.2]oct-1-yl)-ethane or -propane ditriflate (10, 11), and 4,4′-bipyridine respectively. The same technique was employed to convert the complex 4,4′-bipyridine · 2BF3 to the mono-NF derivative F3B-NC5H4-C5H4N+-F BF4- (7) and its monomethylated analogue (4-NC5H4)C5H4N+-CH3 TfO- to F-+ NC5H4-C5H4N+-CH3 (TfO- )2 (8). The results of site-specific electrophilic fluorination of some model substrates (1-morpholinocyclohexene, phenol, 2-naphthol, anisole, di-and tri-methoxybenzene) with 5, 7 and 8 are presented.
Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water
Bora, Pranjal P.,Bihani, Manisha,Plummer, Scott,Gallou, Fabrice,Handa, Sachin
, p. 3037 - 3042 (2019/04/01)
Highly selective direct monofluorination of indoles and arenes was developed through an approach that allows site-specific solubility of substrate and fluorine source in the micelle. This approach was highly selective for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the fine-tuning of selectivity. Control experiments suggested a radical pathway and provided insight into the role of micelles of the environmentally benign amphiphile PS-750-M. Dynamic light scattering experiments strongly indicated the site-specific solubility of the substrate and fluorine source. The methodology was successfully adapted to gram scale, and the E-factor established from a recycle study indicated that the process is environmentally responsible and sustainable.
Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media
Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
experimental part, p. 2394 - 2409 (2009/12/03)
The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl- imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.
