1207299-71-5Relevant academic research and scientific papers
Photoredox-Catalyzed C-F Bond Allylation of Perfluoroalkylarenes at the Benzylic Position
Sugihara, Naoki,Suzuki, Kensuke,Nishimoto, Yoshihiro,Yasuda, Makoto
, p. 9308 - 9313 (2021)
Site-selective and direct C-F bond transformation of perfluoroalkylarenes was achieved with allylic stannanes via an iridium photoredox catalyst system. The present defluoroallylation proceeds exclusively at the benzylic position through perfluoroalkyl radicals generated by a single-electron transfer from an excited photoredox catalyst to perfluoroalkylarenes. A variety of perfluoroalkyl groups are applicable: linear perfluoroalkyl-substituted arenes such as Ar-nC4F9and Ar-nC6F13and heptafluoroisopropylarenes (Ar-CF(CF3)2) underwent site-selective defluoroallylation. DFT calculation studies revealed that thein situgenerated Bu3SnF traps F-to prevent a retroreaction from the unstable perfluoroalkyl radical intermediate, and the radical intermediate favorably reacts with allylic stannanes. The synthesis of a bis(trifluoromethyl)methylene unit containing compound, which is an analog that is useful as a pharmaceutical agent for the prophylaxis or treatment of diabetes and inflammatory diseases, demonstrated the utility of this reaction.
Dialkylzinc-mediated cross-coupling reactions of perfluoroalkyl and perfluoroaryl halides with aryl halides
Kato, Hisano,Hirano, Keiichi,Kurauchi, Daisuke,Toriumi, Naoyuki,Uchiyama, Masanobu
, p. 3895 - 3900 (2014)
A highly chemoselective perfluoroalkylation reaction of aromatic halides is reported. Thermally stable perfluoroalkylzinc reagents, generated by a rapid halogen-zinc exchange reaction between diorganozinc and perfluoroalkyl halide species, couple with a wide range of aryl halides in the presence of a copper catalyst, in moderate to high yields. Good stability of the perfluoroalkylzinc species was indicated by DFT calculation and the reagents were storable for at least three months under argon without loss of activity. This method is applicable to gramscale synthesis, and its functional group tolerance compares favorably with reported protocols.
PERFLUOROALKYLATION REACTION OF AROMATIC COMPOUND
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Paragraph 0042; 0058; 0059, (2018/10/19)
PROBLEM TO BE SOLVED: To provide a novel perfluoroalkylation reaction of an aromatic compound having a perfluoroalkyl group or a fluorophenyl group, which exhibits a high yield and is convenient, and which can be applicable to a wide range of compounds. S
Solvent effects for fluorescence and absorption of tetra (fluoroalkyl) metallophthalocyanines: Fluorocarbon solvent cage
Qiu, Tao,Xu, Xiaoyong,Qian, Xuhong
scheme or table, p. 86 - 91 (2010/12/18)
The UV-vis absorption and fluorescence spectra of a series of tetra (fluoroalkyl) metallophthalocyanines were measured in CH3OH, ethyl acetate, THF, CH2Cl2, C6H6, perfluorooctane. Their absorption spectra and fluorescence spectra were related not only to the peripheral substitutes, but also to the solvent environment. In the strong polar solvents, their maximum absorption and emission wavelengths were blue-shifted. However, in perfluorooctane, the blue shift was found for the absorption, and the red shift for the emission. The fluorocarbon solvent cage concept was put forward to explain this special phenomenon.
