349-50-8Relevant articles and documents
Activation of nucleophilic fluorination by salts in ionic liquids and in sulfolane
Anguille, Stephane,Garayt, Maxime,Schanen, Vincent,Gree, Rene
, p. 1149 - 1153 (2006)
The nucleophilic substitution of PhCCl3 by KF in imidazolium-type RTILs is faster than in classical organic solvents but it is strongly dependent upon the nature of the counteranion. The addition of bromide salts in substoichoimetric amounts to the [bmim][PF6] solvent strongly accelerates this reaction. Furthermore, it has been discovered that addition of KPF6 to the reaction mixtures strongly activates the nucleophilic fluorination by KF, not only in the [bmim][NTf2] or [bmim][PF6] ionic liquids but also for the reactions performed in sulfolane.
Iron-Catalyzed Halogen Exchange of Trifluoromethyl Arenes**
Dorian, Andreas,Landgreen, Emily J.,Petras, Hayley R.,Shepherd, James J.,Williams, Florence J.
supporting information, p. 10839 - 10843 (2021/06/21)
The facile production of ArCF2X and ArCX3 from ArCF3 using catalytic iron(III)halides is reported, which constitutes the first iron-catalyzed halogen exchange for non-aromatic C?F bonds. Theoretical calculations suggest direct activation of C?F bonds by iron coordination. ArCX3 and ArCF2X products of the reaction are synthetically valuable due to their diversification potential. In particular, chloro- and bromodifluoromethyl arenes (ArCF2Cl, ArCF2Br respectively) provide access to a myriad of difluoromethyl arene derivatives (ArCF2R). To optimize for mono-halogen exchange, a statistical method called Design of Experiments was used. Optimized parameters were successfully applied to electron rich and electron deficient aromatic substrates, and to the late stage diversification of flufenoxuron, a commercial insecticide. These methods are highly practical, being run at convenient temperatures and using inexpensive common reagents.
(Re)Investigation of the reactivity of uranium hexafluoride toward several organic functions at room temperature
Roy, Olivier,Marquet, Bernard,Alric, Jean-Paul,Jourdan, Alex,Morel, Bertrand,Langlois, Bernard R.,Billard, Thierry
, p. 74 - 78 (2015/03/04)
The annual worldwide production of UF6 is very large and this compound is not used. Consequently, it could be interesting to find some applications as organic reagent. UF6 could be considered as an oxidizer of various functions. However, it seems also present some possibilities as a fluorinating reagent in mild conditions.
Selective aliphatic fluorination by halogen exchange in mild conditions
Saint-Jalmes, Laurent
, p. 85 - 90 (2007/10/03)
HF-Base media, in particular (HF)10-pyridine or (HF) 3-triethylamine, allow aliphatic chlorine-fluorine exchanges on acid-sensitive molecules. Depending on the nature (pyridine or triethylamine), stoichiometry of the base and temperature, selective mono-, di-, or tri-chlorine-fluorine exchanges on trichloromethyl groups alpha to sulfur, oxygen and carbon atoms can be obtained.