10016-52-1Relevant articles and documents
Alumina-promoted oxodefluorination
Amsharov, Konstantin,Mikhail, Feofanov,Vladimir, Akhmetov
, p. 10879 - 10882 (2020)
A simple protocol for the clean preparation of heterocyclic compounds containing dibenzofuran's core via oxodefluorination of fluoroarenes on activated γ-Al2O3 is reported. Alumina can be considered as a reliable oxygen source enabling one-pot substitution of fluorine atoms and yielding benzoannulated furan derivatives. The corresponding C-F bond activation is selective towards less stable C-Br/C-I and occurs under metal- A nd solvent-free conditions.
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Hoffmeister
, p. 210 (1871)
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Gilman,Ingham
, p. 4843 (1953)
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Simple and efficient synthesis of various dibenzofuran carbaldehydes
Yempala, Thirumal,Cassels, Bruce K.
, p. 1909 - 1915 (2016)
We herein report simple and efficient methods for the synthesis of various formyl derivatives of dibenzofuran. The aldehydes reported are prepared in at most three steps and in yields greater than 60% from commercially available dibenzofuran, with one exception where isomers must be separated. The protocols described involve either formylation of previously functionalized dibenzofuran derivatives or the initial introduction of the formyl group and subsequent further functionalization under standard reaction conditions as described. We have also reported an efficient and simple method for the synthesis of key methoxydibenzofurans in high yield (65% overall for two steps).
Dibenzofuran derivatives with meta- and para-triphenylamine substituents as hole-transporting materials in organic light-emitting devices
Yun, Seong-Jae,Seo, Min Hye,Lee, Sungkoo
, (2020)
Three novel hole-transporting materials, 3,3'-(dibenzo[b,d]furan-2,8-diyl)bis(N,N-diphenylaniline) (BF-m-TPA), 4,4'-(dibenzo[b,d]furan-2,8-diyl)bis(N,N-diphenylaniline) (BF-p-TPA) and 4,4'-(dibenzo[b,d]furan-2,6-diyl)bis(N,N-diphenylaniline) (BF-2,6-TPA), were designed and synthesized. Owing to the rigid dibenzofuran core, these BF-TPA derivatives exhibited high thermal decomposition temperatures of over 395 °C and very high LUMO energy levels. Electroluminescent (EL) devices were fabricated using these three hole-transporting materials. The best device performance was obtained for BF-m-TPA, with the maximum luminance (L) of 15,230 cd/m2, luminance efficiency (LE) of 56.5 cd/A, power efficiency (PE) of 13.3 lm/W, and external quantum efficiency (EQE) of 16.3%.
Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides
Nishii, Yuji,Ikeda, Mitsuhiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro
supporting information, p. 1621 - 1629 (2020/02/04)
A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.
