36375-80-1Relevant academic research and scientific papers
Effective, transition metal free and selective C-F activation under mild conditions
Kong, Xianqiang,Zhang, Huizi,Xiao, Yunqing,Cao, Changsheng,Shi, Yanhui,Pang, Guangsheng
, p. 7035 - 7048 (2015/03/03)
A simple and effective aromatic nucleophilic monosubstitution reaction for the synthesis of aromatic amines via selective C-F bond cleavage of various fluoroarenes (mono-, di-, tri-, tetra-, penta- and perfluorobenzene) with primary and secondary aromatic amines under transition metal free conditions is demonstrated. The reaction conditions were investigated thoroughly for a wide range of fluoroarene substrates bearing different numbers of fluorine atoms, and the results showed that the solvent and reaction temperature are very crucial for the successful substitution reactions. The established methods enabled the formation of nonfluorinated and partially fluorinated aromatic amines in good to excellent yields. Several functional groups were tolerated under the optimized conditions.
Chemistry and kinetics of singlet (pentafluorophenyl)nitrene
Poe, Russell,Schnapp, Karlyn,Young, Mary J.T.,Grayzar, Jennifer,Platz, Matthew S.
, p. 5054 - 5067 (2007/10/02)
The chemistry and kinetics of singlet (pentafluorophenyl)nitrene were studied by chemical trapping and laser flash photolysis techniques. Photolysis of pentafluorophenyt azide in cyclohexane, benzene, diethylamine, pyridine, tetramethylethylene, tetrahydrofuran, dimethyl sutfoxide, and dimethyl sulfide forms adducts in fair to good yields. At ambient temperature singlet (pentafluorophenyl)nitrene is intercepted, and intersystem crossing to the lower energy triplet state is unimportant. Triplet nitrene chemistry can be achieved by benzoylbiphenyl photosensitization, the presence of methanol or ethyl iodide, or by lowering the reaction temperature below 0 °C. The singlet nitrenc adduct formed in pyridine is an ylide whose structure has been determined by X-ray crystallography. The ylide has an intense absorption maximum at 390 nm which varies only slightly with solvent. The pyridine ylicle is a useful probe for monitoring the absolute kinetics of singlet (pentafluorophenyl)nitrene by laser flash photolysis techniques.
