10386-84-2Relevant articles and documents
One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding
Baykov, Sergey V.,Eliseeva, Anastasiya A.,Frontera, Antonio,Galmés, Bartomeu,Kukushkin, Vadim Yu.,Rozhkov, Anton V.
, p. 5908 - 5921 (2020)
Perfluorinated arenes (benzeneF derivatives, diphenylF, naphthaleneF) were converted into X-perfluoroarenes (X = Br, I) via the developed one-pot protocol based on [Fe(acetylacetonate)3]-assisted C-F functionalization. The syntheses proceed under mild conditions and employ readily available perfluorinated arenes, which are treated with EtMgBr followed by addition of X2/[Fe(acetylacetonate)3] (0.8 mol %); yields range from good to moderate. The σ-hole donor properties of the obtained mono- and di-X-perfluoroarenes and the significance of these species for halogen-bonding-based crystal engineering was illustrated in a series of postsynthetic experiments, all supported by density functional theory (DFT) energy calculations, molecular electrostatic potential (MEP) surface analysis, and the quantum theory of atoms in molecules (QTAIM). These include (i) a solid-state X-ray diffraction study of X-perfluoroarene self-association (dimerization) via iodine σ-hole - electron belt interactions (three X-ray structures) and (ii) verification of X-perfluoroarene σ-hole donor abilities by their interactions with iodides acting as external σ-hole acceptors (five X-ray structures); a Hirshfeld surface analysis was performed for all eight structures.
Synthesis of Bromochloropolyfluorobiphenyls Containing Bromine and Chlorine Atoms in the 4 and 4,4′ Positions
Maksimov, A. M.,Nikul’shin, P. V.,Platonov, V. E.
, p. 1316 - 1324 (2021/08/13)
Abstract: A new method for the synthesis of 4-chlorononafluoro- and 4-bromononafluorobiphenyl by the reactions of nonafluorobiphenyl-4-thiol with Cl2, PCl5, and Br2, as well as of 4,4′-dichlorooctafluorobiphenyl from octafluorobiphenyl-4,4′-dithiol, 4′-chlorooctafluorobiphenyl-4-thiol, Cl2, and PCl5 was developed. 4-Bromo-4′-chlorooctafluorobiphenyl was synthesized for the first time from 4′-chlorooctafluorobiphenyl-4-thiol and Br2. 4,4′-Dichlorooctafluorobiphenyl was obtained as the main product in the reaction of 4′-bromooctafluorobiphenyl-4-thiol with PCl5. [Figure not available: see fulltext.].