Beilstein J. Org. Chem.2017,13, 2690–2697, doi:10.3762/bjoc.13.267
, Kashiwara, Osaka 582-8582, Japan 10.3762/bjoc.13.267 Abstract A series of aniline and m-phenylenediamine derivatives with electron-withdrawing 3,3,3-trifluoropropenyl substituents were synthesized as small and chemically stable fluorescent organic compounds. Their fluorescence performances were evaluated
push–pull system, which has a single benzene ring substituted by both electron-donating and electron-withdrawing groups [15][16][17]. We focused on the 3,3,3-trifluoropropenyl (TFPE) group, which is an electron-withdrawing substituent that is free of oxygen atoms, which would form hydrogen bonds in
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Graphical Abstract
Figure 1:
(a) UV–vis absorption and (b) fluorescence spectra of 1–4 in THF.
Beilstein J. Org. Chem.2013,9, 2417–2421, doi:10.3762/bjoc.9.279
reaction involves oxidative 3,3,3-trifluoropropylation of an arylaldehyde to afford 4,4,4-trifluoro-1-arylbutan-1-one.
Keywords: cesium fluoride; organo-fluorine; 1,3-proton shift; trifluoromethyl; 3,3,3-trifluoropropenyl; Introduction
Trifluoromethyl groups are an essential motif in pharmaceuticals
used in place of (3,3,3-trifluoropropynyl)lithium, which can add to carbonyl compounds and couple with aryl halides through a zinc intermediate. For the 3,3,3-trifluoropropenyl synthon Yamazaki et al. reported the use of 2-(trifluoromethyl)-1-(phenylsulfenyl)vinyltrimethylsilane for the addition to
aldehydes in the presence of fluoride anion [29]. Recently, Prakash et al. [30] reported the synthesis of β-trifluoromethylstyrenes through a Heck coupling reaction of aryl iodides with 1-iodo-3,3,3-trifluoropropane, allowing a direct introduction of 3,3,3-trifluoropropenyl groups to aromatic rings
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Graphical Abstract
Scheme 1:
Experiments to elucidate the reaction mechanism.