541549-19-3Relevant articles and documents
2-(Fluorophenyl)pyridines by the Suzuki-Miyaura method: Ag2O accelerates coupling over undesired ipso substitution (SNAr) of fluorine
Chen, Jing,Cammers-Goodwin, Arthur
, p. 1503 - 1506 (2003)
Problematic ipso substitution was observed in the Suzuki-Miyaura coupling of pentafluorophenylboronic acid to make 2-pentafluorophenylpyridine. Strong bases favored coupling, but under these conditions fluorine in the product tended to undergo nucleophili
Highly efficient heterogeneous copper-catalyzed decarboxylative cross-coupling of potassium polyfluorobenzoates with aryl halides leading to polyfluorobiaryls
Lin, Yang,Cai, Mingzhong,Fang, Zhiqiang,Zhao, Hong
, p. 34722 - 34729 (2017/07/22)
The heterogeneous decarboxylative cross-coupling reaction of potassium polyfluorobenzoates with aryl iodides and bromides was achieved in diglyme or DMAc at 130 or 160 °C in the presence of 10-20 mol% of a 1,10-phenanthroline-functionalized MCM-41-immobilized copper(i) complex, [MCM-41-Phen-CuI], yielding a variety of polyfluorobiaryls in good to excellent yields. This heterogeneous copper(i) complex could easily be prepared via a simple procedure from commercially readily available and inexpensive reagents, exhibited the same catalytic activity as the homogeneous CuI/Phen system, and was recovered by filtration of the reaction solution and recycled at least 8 times without significant loss of catalytic activity.
The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH2Hal (Hal=Br, Cl)
Shabalin, Anton Yu.,Adonin, Nicolay Y.,Bardin, Vadim V.,Parmon, Valentin N.
, p. 3720 - 3725 (2014/05/20)
The influence of the ligand nature on catalytic activity of palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate, which imitates the behavior of electron-deficient organoboron reagents, with aryl halides, ArHal (Hal=Br, Cl) was studied. The activity of the catalysts generated in situ from Pd(OAc) 2 and appropriate phosphorous containing ligands and the reaction selectivity was found to depend on the nature of bulky phosphines used as ligands. As a result, conditions for involving the electron-deficient organoboron reagent - potassium pentafluorophenyltrifluoroborate - in the palladium-catalyzed cross-coupling with aryl bromides and aryl chlorides were identified. It was demonstrated that the chosen conditions are appropriate for the reaction of K[C6F5BF3] with benzyl chloride and benzyl bromide deriving pentafluorophenylarylmethanes, C6F 5CH2Ar.
