ChemInform Abstract: Ruthenium‐Catalyzed Cross‐Dehydrogenative ortho‐N‐Carbazolation of Diarylamines: Versatile Access to Unsymmetrical Diamines.

Louillat, Marie‐Laure; Biafora, Agostino; Legros, Fabien; Patureau, Frédéric W.

doi:10.1002/chin.201436050

Cited by 3 publications

(3 citation statements)

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“…The latter site is typically alkylated in the presence of a base, although a Ru-catalyzed dehydrogenative N-arylation was recently reported (Scheme 48). 248 46.4 is readily brominated at positions 3 and 10, opening a convenient path for further functionalization.…”

Section: [Ghi]heteroannulated Perylenoids: 5-membered Ringsmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

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Section: [Ghi]heteroannulated Perylenoids: 5-membered Ringsmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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“…The stepwise synthesis of dyes 1 and 2 was depicted in Scheme 2. Bromination of carbazole 3 was performed in nearly quantitative yield according to the publication by M. Ludwiczak et al, 30 followed by an Ullmann coupling modified from a literature procedure 31 to give dimethoxy derivative 5. Prey demethylation (pyridinium hydrochloride at high temperature) adapted from a literature report 32,33 gave the 3,6-dihydroxy-9H-carbazole 6 in 89% yield.…”

Section: Resultsmentioning

confidence: 99%

Deep Blue Asymmetrical Streptocyanine Dyes: Synthesis, Spectroscopic Characterizations, and Ion-Specific Cooperative Adsorption at the Surface of TiO₂ Anatase Nanoparticles

et al. 2017

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Various triflate (TfO–), tetrafluoroborate (BF4 –), and perchlorate (ClO4 –) salts of (E)-9-(3-(4-(diphenylamino)phenyl)allylidene)-9H-carbazol-9-ium chromophores, asymmetrical streptocyanine blue dyes, were synthesized, and their structures and photochemical and electrochemical properties were characterized. Displaying a high absorption band in the wavelength range 620–640 nm in acidified benzonitrile, the dyes provide an intense absorption at longer wavelength thanks to their oxidized π-conjugated systems. The π-electronic structure underwent twisting and bending, counteracting the electron-donating/withdrawing induction of its different substituents with a propensity to cancel its dipole moment and HOMO–LUMO charge-transfer coefficient. Zeta potential measurements of colloidal suspensions of sensitized TiO2 anatase nanoparticles outlined the difference in electric behavior of the organic ionic pairs at the surface of the nanoparticles: The noncoordinating or coordinating characters of the counterions were found governing the molecular density at the surface and the adsorption/desorption kinetics of the ionic pairs. Dye-sensitized solar cell (DSSC) measurements performed with I–/I3 – as redox shuttle outlined the availability of the dyes for solar cell sensitization and the conditions for best stability/efficiency of such π-conjugated structures according to the nature of the counterion.

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“…The reaction proceeded through either in situ formation of NH(OAc) or the Michael-type intermediate. However, to the best of our knowledge, there is no example of non-directed catalytic C–H bond activation of unprotected primary anilines 34 35 .…”

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confidence: 99%

Reversed reactivity of anilines with alkynes in the rhodium-catalysed C–H activation/carbonylation tandem

et al. 2015

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Development of multicatalytic approach consisting of two or more mechanistically distinct catalytic steps using a single-site catalyst for rapid and straightforward access of structurally complex molecules under eco-benign conditions has significance in contemporary science. We have developed herein a rhodium-catalysed C–H activation strategy which uses an unprotected anilines and an electron-deficient alkynes to C–C bonded products as a potential intermediate in contrast to the archetypical C–N bonded products with high levels of regioselectivity. This is followed by carbonylation of C–H bond activated intermediate and subsequent annulation into quinolines has been described. This rhodium-catalysed auto-tandem reaction operates under mild, environmentally benign conditions using water as the solvent and CO surrogates as the carbonyl source with the concomitant generation of hydrogen gas. The strategy may facilitate the development of new synthetic protocols for the efficient and sustainable production of chemicals in an atom-economic way from simple, abundant starting materials.

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ChemInform Abstract: Ruthenium‐Catalyzed Cross‐Dehydrogenative ortho‐N‐Carbazolation of Diarylamines: Versatile Access to Unsymmetrical Diamines.

Cited by 3 publications

References 1 publication

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Deep Blue Asymmetrical Streptocyanine Dyes: Synthesis, Spectroscopic Characterizations, and Ion-Specific Cooperative Adsorption at the Surface of TiO₂ Anatase Nanoparticles

Reversed reactivity of anilines with alkynes in the rhodium-catalysed C–H activation/carbonylation tandem

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ChemInform Abstract: Ruthenium‐Catalyzed Cross‐Dehydrogenative ortho‐N‐Carbazolation of Diarylamines: Versatile Access to Unsymmetrical Diamines.

Cited by 3 publications

References 1 publication

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Deep Blue Asymmetrical Streptocyanine Dyes: Synthesis, Spectroscopic Characterizations, and Ion-Specific Cooperative Adsorption at the Surface of TiO2 Anatase Nanoparticles

Reversed reactivity of anilines with alkynes in the rhodium-catalysed C–H activation/carbonylation tandem

Contact Info

Product

Resources

About

Deep Blue Asymmetrical Streptocyanine Dyes: Synthesis, Spectroscopic Characterizations, and Ion-Specific Cooperative Adsorption at the Surface of TiO₂ Anatase Nanoparticles