491854-48-9Relevant academic research and scientific papers
Oxygenative perfluoroalkylation of olefinic compounds using perfluoroalkyl iodide in the presence of oxygen
Yoshida, Masato,Ohkoshi, Masanori,Muraoka, Tsunehiro,Matsuyama, Haruo,Iyoda, Masahiko
, p. 1833 - 1842 (2002)
Reactions of perfluoroalkyl iodides with styrene and its derivatives were investigated under radical conditions in the presence of oxygen. The photochemical reaction of styrene with CF3(CF2)5I in the presence of tributyltin hydride or tris(trimethylsilyl)silane under an oxygen atmosphere afforded the corresponding perfluoroalkylated alcohols in moderate yields together with CF3(CF2)5H. However, the photochemical reactions of styrene and its derivatives with CF3(CF2)nI (n = 3, 5) in the presence of hexabutylditin under oxygen produced the perfluoroalkylated alcohols in good yields. Furthermore, the reactions of styrenes with CF3(CF2)nI (n = 3, 5, 9) and Na2S2O4 in the presence of a base under air formed the same alcohols in good yields. The alcohols were found to provide a novel type of α-fluoroalkylated styrenes by acidic dehydration. Perfluoroalkylated α,β-unsaturated ketones were synthesized by oxygenative perfluoroalkylations of α-chlorostyrene and its derivatives using CF3(CF2)nI (n = 3, 5) under radical reaction conditions. The ketones were found to be good synthetic building blocks for perfluoroalkylated heterocycles, such as pyrazoles, dihydrodiazepines, pyrimidines, and isoxazoles.
Perfluoroalkylation of α-methylstyrene using titanium oxide as a photocatalyst
Iizuka, Mari,Fukushima, Shoju,Yoshida, Masato
, p. 1042 - 1043 (2007)
A redox system for fluoroalkylation with perfluoroalkyl iodide using TiO2 as a photocatalyst was developed. Photoirradiation of perfluoroalkyl iodide and α-methylstyrene in CH3CN in the presence of TiO2 and NaBF4/sub
Redox system for perfluoroalkylation of arenes and α-methylstyrene derivatives using titanium oxide as photocatalyst
Iizuka, Mari,Yoshida, Masato
experimental part, p. 926 - 932 (2010/01/15)
Photoirradiation of titanium oxide (TiO2) excites the electrons from the valence band to the conduction band, leaving holes in the valence band. Using these holes and electrons, it is possible to perform one-electron oxidations and reductions. We developed a method for the photocatalytic perfluoroalkylation of aromatic rings such as benzene and its derivatives, naphthalene and benzofuran with perfluoroalkyl iodide by the combination of reduction and oxidation reactions with TiO2. Perfluoroalkyl iodide was reduced to a perfluoroalkyl radical by the excited electrons in the conduction band of TiO2, and the resulting radical reacted with an aromatic ring to form an arenium radical that was successively oxidized to a cation by the holes in the valence band of TiO2. Similarly, the photocatalytic reaction of α-methylstyrene with perfluoroalkyl iodide afforded perfluoroalkylated α-methylstyrene, in which the perfluoroalkyl group is on a methyl carbon.
