344-04-7Relevant articles and documents
Yakobson,Vlasov
, p. 652,662 (1976)
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Hellmann et al.
, p. 5654,5656 (1957)
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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 (2020/10/13)
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.
Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
Quibell, Jacob M.,Perry, Gregory J. P.,Cannas, Diego M.,Larrosa, Igor
, p. 3860 - 3865 (2018/04/26)
Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.
Method for preparing 2,3,4,5,6-pentafluorophenol
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Paragraph 0096; 0097, (2017/08/29)
The invention discloses a method for preparing 2,3,4,5,6-pentafluorophenol. The method comprises the following step of in water, performing an oxidation reaction on 2,3,4,5,6-pentafluoro phenylboronic acid as shown in the formula (VI) and hydrogen peroxide, thereby obtaining 2,3,4,5,6-pentafluorophenol as shown in the formula (VII). According to the method, an oxidation reaction is implemented in the water, so that the method is low in cost, and environmental-friendly; and besides, the method is high in reaction yield and purity and relatively applicable to industrial production.