114467-76-4Relevant articles and documents
Synthesis of ArCF2X and [18F]Ar-CF3via Cleavage of the Trifluoromethylsulfonyl Group
Yang, Ren-Yin,Gao, Xinyan,Gong, Kehao,Wang, Juan,Zeng, Xiaojun,Wang, Mingwei,Han, Junbin,Xu, Bo
, p. 164 - 168 (2021/12/17)
A versatile synthesis of ArCF2X and [18F]Ar-CF3 type compounds from readily available ArCF2SO2CF3 has been developed. Diverse nucleophiles, including weak nucleophiles such as halides (18F-, Cl-, Br-, and I-), RSH, and ROH, could react with ArCF2SO2CF3 efficiently to give the corresponding difluoromethylene products. The control experiments and the Hammett plot indicated that the reaction might proceed through a difluorocarbocation intermediate generated from the steric hindrance-assisted cleavage of the trifluoromethylsulfonyl group.
Silver-Mediated 18F-Labeling of Aryl-CF3 and Aryl-CHF2 with 18F-Fluoride
Verhoog, Stefan,Pfeifer, Lukas,Khotavivattana, Tanatorn,Calderwood, Samuel,Collier, Thomas Lee,Wheelhouse, Katherine,Tredwell, Matthew,Gouverneur, Véronique
supporting information, p. 25 - 28 (2015/12/26)
We report the synthesis of [18F]arylCF3 and [18F]arylCHF2 derivatives from arylCF2Br and arylCHFCl precursors applying a silver-mediated halogen exchange with [18F]fluoride. In the absence of Ag(I)OTf, no reaction takes place at room temperature for both classes of substrates; this result demonstrates the beneficial role of silver(I) as a means to induce 18F-incorporation under very mild conditions.
Syntheses of New Aromatic Compounds with Fluorinated Side Chains and their Chemical Reactivity
Haas, Alois,Spitzer, Martin,Lieb, Max
, p. 1329 - 1340 (2007/10/02)
The syntheses of a wide range of aromatic compounds of the type p-Y-C6H4CF2X(4-13) are described, and the chemical behavior of these compounds as a function of substituent Y is investigated .Analogously the pyridine derivatives 15, 17, and 18 were synthesized and characterized.From a correlation of the 19F-NMR data of these compounds with the Hammett constant of Y, participation of C-F ?-back-donation is seen as the cause for an observed shift of the 19F signals to lower field.
