2398-79-0Relevant academic research and scientific papers
Radical fluoroalkylation reactions of (hetero)arenes and sulfides under red light photocatalysis
Yerien, Damian E.,Cooke, M. Victoria,García Vior, M. Cecilia,Barata-Vallejo, Sebastián,Postigo, Al
supporting information, p. 3741 - 3746 (2019/04/17)
Fluoroalkylation reactions of (hetero)aromatics have been accomplished through the low-power illumination from red LEDs (λmax = 635 nm) of commercially available perfluoroalkyl iodides RF-I and phthalocyanine zinc salt as photocatalyst in MeCN?:?DMF solvent mixture. This methodology has been extended to the perfluorobutylation of sulfides. As far as we are concerned, this is the first report on a perfluoroalkylation reaction of (hetero)aromatics and sulfides under red-light photocatalysis.
Benign Perfluoroalkylation of Aniline Derivatives through Photoredox Organocatalysis under Visible-Light Irradiation
Barata-Vallejo, Sebastián,Yerien, Damian E.,Postigo, Al
supporting information, p. 7869 - 7875 (2015/12/24)
In this work, we present a room- or solar-light-initiated transition-metal-free radical homolytic aromatic substitution (HAS) reaction of aniline derivatives with perfluoroalkyl moieties employing perfluoroalkyl halides as readily available perfluoroalkyl
A general, regiospecific synthetic route to perfluoroalkylated arenes via arenediazonium salts with RFCu(CH3CN) complexes
Jiang, Dong-Fang,Liu, Chao,Guo, Yong,Xiao, Ji-Chang,Chen, Qing-Yun
supporting information, p. 6303 - 6309 (2015/03/30)
A mild method of converting arylamines into perfluoroalkylated arenes is described. Relatively stable RFCu(CH3CN) complexes are used as perfluoroalkylating agents, which react smoothly with arenediazonium salts to produce various perfluoroalkylarenes in good yields. Based on the results of clock trapping experiments with diallyl ether, a radical process might be involved in the reaction.
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
