344452-99-9Relevant academic research and scientific papers
Synthesis of potassium 4-(1-azol-1-yl)-2,3,5,6- tetrafluorophenyltrifluoroborates from K[C6F5BF 3] and alkali metal azol-1-ides. the dramatic distinction in nucleophilicity of alkali metal azol-1-ides and dialkylamides
Shabalin, Anton Yu.,Adonin, Nicolay Yu.,Bardin, Vadim V.,Taran, Oksana P.,Ayusheev, Artemiy B.,Parmon, Valentin N.
, p. 290 - 297 (2013)
Nucleophilic substitution of fluorine atom in K[C6F 5BF3] with alkali metal azol-1-ides in polar aprotic solvent (DMF, DMSO) at 60-130 C gives potassium 4-(azol-1-yl)-2,3,5,6- tetrafluorophenyltrifluoroborates, K[4-AzC6F4BF 3] (AzH = pyrrole, pyrazole, imidazole, indole, and benzimidazole). Unexpectedly, diethylamine and morpholine do not react with K[C 6F5BF3] under the same conditions while pentafluorobenzene and R2NC6F4H form at 150 C. Reaction of K[C6F5BF3] with Na[NR2] in diglyme or DMSO proceeds similar way. The assumed reason is the relatively low nucleophilicity of both secondary amines and alkali metal dialkylamides which results in destructive by-reaction with K[C6F 5BF3] rather than in its aminodefluorination. This is confirmed by the competitive nucleophilic aminodefluorination of a model substrate, C6F5Ph, with sodium indolide/sodium morpholinide.
Selective C4-F bond cleavage of pentafluorobenzene: Synthesis of N-tetrafluoroarylated heterocyclic compounds
Liu, Cuibo,Wang, Huan,Xing, Xing,Xu, You,Ma, Jun-An,Zhang, Bin
supporting information, p. 4649 - 4652 (2013/08/23)
A simple aromatic nucleophilic monosubstitution reaction for the synthesis of N-tetrafluoroarylated heterocyclic compounds via selective C4-F bond cleavage of pentafluorobenzene with N-H containing heterocycles is demonstrated. This method is highly tolerant of a wide range of substrates to give the corresponding products in moderate to good yields. Additionally, this strategy is applied to synthesize other mono-, di-, and tri-fluoroarylated indole derivatives. Crown Copyright
