29778-93-6Relevant academic research and scientific papers
Palladium-catalyzed desulfitative direct C-H arylation of electron-deficient polyfluoroarenes with sodium arenesulfinates
Miao, Tao,Wang, Lei
, p. 429 - 436 (2014)
The palladium-catalyzed direct arylation of electron-deficient polyfluorobenzenes was developed in the presence of silver carbonate and trisodium phosphate. This protocol allowed use of both electron- deficient and electron-rich aromatic sulfinic acid sodium salts as arylating reagents for the direct arylation of a variety of polyfluoroarenes to produce fluorobiaryls in good to excellent yields, providing a complement to the existing methods for the direct arylation of polyfluoroarenes.
Direct palladium-catalyzed desulfitative CC coupling of polyfluoroarenes with arylsulfinate salts: Water-accelerated reactions
Lin, Xiaoxi,You, Yi,Weng, Zhiqiang
, p. 76 - 80 (2014/07/22)
A new approach to the synthesis of fluorinated biaryl compounds from easily available starting materials is described. This protocol is based on the direct palladium-catalyzed desulfitative cross-coupling of polyfluoroarenes with various arylsulfinate salts via CH bond activation, accelerated by trace amount of water. The method allows the synthesis of various fluorinated biaryl products in moderate to good yields, and tolerated a variety of functional groups, including alkyl, phenyl, methoxy, fluoro, and chloro groups.
Air-stable and catalytically active phosphinous acid transition-metal complexes
Kurscheid, Boris,Belkoura, Lhoussaine,Hoge, Berthold
experimental part, p. 1329 - 1334 (2012/04/10)
Secondary phosphane oxides R2P(O)H are most frequently used as preligands for phosphinous acid R2POH (R = alkyl, aryl) transition-metal complexes, which are very efficient catalysts for cross-coupling reactions. To investigate the influence of electron-deficient substituents on the catalytic activity, the coordination properties of bis(trifluoromethyl)-, bis(pentafluoroethyl)-, and bis[2,4-bis(trifluoromethyl) phenyl]phosphinous acid toward catalytically relevant metals, such as palladium and platinum, are studied. The novel phosphinous acid palladium complexes reveal a high catalytic activity in Heck and Suzuki cross-coupling reactions. Because of the strong dependence of these processes on the reaction conditions, a systematic solvent and base screening with 1-bromo-3-fluorobenzene and phenyl boronic acid as model reactants is performed. The most efficient solvent/base system consists of 2-propanol and potassium phosphate, providing a full conversion and a TON of around 10 000 after 20 h at room temperature with a catalyst loading of 0.01 mol % palladium. A catalyst loading of only 0.004 mol % palladium still leads to a nearly full conversion after 20 h at room temperature. During the catalytic reaction, the formation of the corresponding phosphinic acid R2P(O)OH is observed. Further investigations lead to the conclusion that palladium nanoparticles represent the catalytically active species. We also succeeded in the generation of palladium nanoparticles, which exhibit an extremely high catalytic activity in Suzuki cross-coupling reaction with TONs over 60 000 and TOFs larger than 40 000.
The effect of N-heterocyclic carbene ligands in the palladium-catalyzed cross-coupling reaction of K[C6F5BF3] with aryl iodides and aryl bromides
Adonin, Nicolay Yu.,Babushkin, Dmitrii E.,Parmon, Valentin N.,Bardin, Vadim V.,Kostin, Gennadiy A.,Mashukov, Vasiliy I.,Frohn, Hermann-Josef
, p. 5920 - 5924 (2008/09/21)
The effect of N-heterocyclic carbene (NHC) ligands on the catalytic activity of in situ generated palladium complexes in the model cross-coupling reaction of K[C6F5BF3] with 4-FC6H4I was studied. Based on the obtained results, a series of pentafluorobiphenyls C6F5C6H4X were prepared from K[C6F5BF3] and XC6H4I or 4-CF3C6H4Br in high yields under aerobic conditions.
Reactions of pentafluorophenylxenon(II) hexafluoroarsenate (+)(-) with aromatic compounds
Frohn, H. J.,Klose, A.,Bardin, V. V.
, p. 201 - 216 (2007/10/02)
Pentafluorophenylxenon(II) hexafluoroarsenate (+)(-) reacts (MeCN, 20 deg C) with aromatic compounds C6H5X (X=CH3, F, CF3, NO2 and CN), yielding isomeric mixtures of polyfluorinated biphenyls XC6H4C6F5.When X=I, iodopentafluorobenzene is formed in addition, whereas trimethylsilylbenzene (X=SiMe3) is only converted to C6H5C6F5 and C6F5H.These results are compared with the data for the radical pentafluorophenylation and fluorination reactions of the corresponding aromatic compounds with XeF2.Polyfluoroaromatic compounds C6F6, C6F5H, C6F5I, C6F5CN and C6F5SiMe3 do not react with (+)(-) under the same conditions.
