Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

Rahman, Md. Shafiqur; Yoshikai, Naohiko

doi:10.3762/bjoc.16.48

Cited by 2 publications

(2 citation statements)

References 40 publications

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“…Next, we attempted to construct a novel biplanar molecule, i.e., 7,7′-bidibenzo[ f , h ]pyrazolo[1,5- a ]quinoline, with extended π conjugation. The application of hypervalent iodine reagents, e.g., phenyliodine(III) bis(trifluoroacetate) (PIFA) and phenyliodine(III) bis(acetate) (PIDA), in the presence of a BF 3 ·OEt 2 Lewis acid, however, did not transform the 4a precursor into the targeted oxidatively-coupled cyclo-product through a Scholl reaction route. Instead, we discovered that mono- and di-chlorinated compounds 5a (50% yield) and 5a ′ (68% yield) were produced (Scheme ) serendipitously when the aforementioned reactions were further quenched by the addition of NH 4 Cl (aq), respectively.…”

Section: Resultsmentioning

confidence: 94%

Synthesis and Mechanistic Investigation of Bipyrazolo[1,5-a]pyridines via Palladium-Catalyzed Cross-Dehydrogenative Coupling of Pyrazolo[1,5-a]pyridines

et al. 2022

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The synthesis of a range of 3,3′-bipyrazolo[1,5-a]pyridine derivatives via direct cross-dehydrogenative coupling of pyrazolo[1,5-a]pyridine precursors is herein presented. This simple and efficient methodology involving palladium(II)-catalyzed C–H bond activation showed good functional group tolerance and product yield (up to 94%). Through the mechanistic insights gained from both kinetic isotope effect experimental studies and density functional theory calculations, a plausible reaction mechanism was outlined. Furthermore, subsequent derivatizations of the resulting 7,7′-diaryl-3,3′-bipyrazolo[1,5-a]pyridines, executed by performing palladium-mediated ortho C–H bond activation followed by hypervalent iodine-induced chlorination, rendered this series of compounds more extended π-conjugation and twisted conformations. Our study on these bipyrazolo[1,5-a]pyridine-based luminogens provides new opportunities for tailor-made organic luminescent materials.

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Section: Resultsmentioning

confidence: 94%

Synthesis and Mechanistic Investigation of Bipyrazolo[1,5-a]pyridines via Palladium-Catalyzed Cross-Dehydrogenative Coupling of Pyrazolo[1,5-a]pyridines

et al. 2022

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“…Hydroxycalixarene itself has a natural coordinating group in the form of a hydroxyl group. As the “holy grail” of chemistry, hydroxycalixarene, specifically its derivatives, have good coordination adsorption properties and have often been used for heavy metal ion adsorption research 8,9 . However, the hydroxycalixarene molecule itself has poor water solubility, and protonated hydroxycalixarene usually needs to go through a tedious intermediate treatment process before it can effectively adsorb heavy metal ions 10,11 .…”

Section: Introductionmentioning

confidence: 99%

Coordination binding of hydroxycalix[4]arene, hydroxycalix[5]arene, and hydroxycalix[6]arene to uranyl and thorium ions

Lan¹,

Wang²,

Liu³

et al. 2023

Applied Organom Chemis

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In this study, hydroxycalix[4]arene, hydroxycalix[5]arene, hydroxycalix[6]arene, and their complexes with uranyl and thorium ions were analyzed by density functional theory. The coordination ability of hydroxycalixarene ligands to uranyl and thorium ions could be analyzed by simulating the infrared and ultraviolet–visible spectra, the Wiberg bond energy levels, the energy gaps, and the binding energies. We found that various hydroxycalixarene complexes with uranyl or thorium ions had significant differences in their properties, as well as in their infrared vibrational and ultraviolet absorption spectra. More importantly, different hydroxycalixarenes can be selected based on the adsorption requirements in environments with coexisting uranium and thorium ions. For example, hydroxycalix[4]arene and hydroxycalix[5]arene had a significantly higher binding capacities for thorium than uranyl ions, while hydroxycalix[6]arene showed less of a difference for the two ions but had a good binding ability for both uranyl and thorium ions at the same time. Thus, the use of hydroxycalixarene can achieve the removal of both uranyl and thorium ions in the environment, and the use of specific hydroxycalixarenes may be able to achieve the separation of these ions. These results provide important guidance for the future research of hydroxycalixarene without requiring the synthesis of hydrophilic derivatives, and they may be directly applied to the field of heavy metals.

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Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

Cited by 2 publications

References 40 publications

Synthesis and Mechanistic Investigation of Bipyrazolo[1,5-a]pyridines via Palladium-Catalyzed Cross-Dehydrogenative Coupling of Pyrazolo[1,5-a]pyridines

Synthesis and Mechanistic Investigation of Bipyrazolo[1,5-a]pyridines via Palladium-Catalyzed Cross-Dehydrogenative Coupling of Pyrazolo[1,5-a]pyridines

Coordination binding of hydroxycalix[4]arene, hydroxycalix[5]arene, and hydroxycalix[6]arene to uranyl and thorium ions

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