153910-98-6Relevant articles and documents
Copper-Catalyzed Oxidative Perfluoroalkylation of Aryl Boronic Acids Using Perfluoroalkylzinc Reagents
Bao, Xifei,Liu, Lihua,Li, Junlan,Fan, Shilu
, p. 463 - 468 (2018/02/19)
An efficient and synthetically convenient method for copper-catalyzed cross-coupling of aryl boronic acids with perfluoroalkyl zinc reagents has been described. The reaction proceeds under mild reaction conditions with a high efficiency and broad substrate scope and provides a general access to perfluoroalkylated arenes, which are of interest in life and materials science.
Approaches to prepare perfluoroalkyl and pentafluorophenyl copper couples for cross-coupling reactions with organohalogen compounds
Kremlev, Mikhail M.,Mushta, Aleksej I.,Tyrra, Wieland,Yagupolskii, Yurii L.,Naumann, Dieter,Sch?fer, Mathias
, p. 19693 - 19699 (2015/11/27)
The reactions of iodoperfluoroalkanes CnF2n+1I (n = 2, 3, 4) and n-BuLi at low temperatures give NMR spectroscopic evidence for LiCnF2n+1 which were converted into LiCu(CnF2n+1)2 derivatives upon treatment with 0.5 mol copper(i) bromide, CuBr. An alternative route to obtain perfluoroorgano copper couples, Cu(Rf)2Ag (Rf = n-C3F7, n-C4F9, C6F5) was achieved from the reactions of the corresponding perfluoroorgano silver(i) reagents, AgRf, and elemental copper through redox transmetallations. The composition of the resulting reactive intermediates was investigated by means of 19F NMR spectroscopy and ESI mass spectrometry. Perfluoro-n-propyl and perfluoro-n-butyl copper-silver reagents prepared by the oxidative transmetallation route exhibited good properties in C-C bond formation reactions with acid chlorides even under moderate conditions. Substitution of bromine directly bound to aromatics for perfluoroalkyl groups was achieved at elevated temperatures, while success in halide substitution reactions using lithium copper couples remained poor.
Heterogeneous photoinduced homolytic aromatic substitution of electron-rich arenes with perfluoroalkyl groups in water and aqueous media - A radical-ion reaction
Barata-Vallejo, Sebastian,Flesia, Marina Martin,Lantano, Beatriz,Argueello, Juan E.,Penenory, Alicia B.,Postigo, Al
, p. 998 - 1008 (2013/03/14)
The photoinduced electron transfer (PET) substitution reaction of electron-rich aromatic nuclei with perfluoroalkyl Rf groups was carried out in water or aqueous mixtures to render substitution products resulting from replacement of aromatic H atoms with the Rf moiety in good yields (57-88 %). Some mechanistic aspects are discussed, supporting the notion of a PET reaction leading to a classical radical homolytic aromatic substitution (HAS) followed by an electron transfer (ET) and then a proton transfer (PT) sequence. A radical mechanism superimposed on a redox process is proposed to account for product formation. Evidence for the radical cation species (as an initiation event) generated from electron-rich arenes in the presence of perfluoroalkyl halides is provided by the UV/Vis transient spectra obtained by Nanosecond Laser Flash Photolysis techniques. Copyright
