Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis

Du, Fangyu; Zhou, Qifan; Liu, Dongdong; Fang, Ting; Shi, Yajie; Du, Youwei; Chen, Guoliang

doi:10.1055/s-0036-1591892

Cited by 16 publications

(3 citation statements)

References 14 publications

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“…First, the pyrazole-based ligand was synthesized via Suzuki coupling and then reacted with IrCl 3 ·3H 2 O to obtain the chloro-bridged Ir dimer [Ir(ppfn) 2 Cl] 2 . Afterward, the reaction exhibiting various electron-push–pull pyridine-based N∧N ligands ( dtbp , dpph , domp , fomp , and dfbp ( 39 )) and anion–exchange reactions from Cl – to PF 6 – yielded complexes DTBP – DFBP . All of the targeted complexes were purified with silica gel column chromatography.…”

Section: Resultsmentioning

confidence: 99%

Cationic Ir(III) Complexes with 4-Fluoro-4′-pyrazolyl-(1,1′-biphenyl)-2-carbonitrile as the Cyclometalating Ligand: Synthesis, Characterizations, and Application to Ultrahigh-Efficiency Light-Emitting Electrochemical Cells

Yi,

Lee,

Huang

et al. 2024

Inorg. Chem.

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Light-emitting electrochemical cells (LECs) promise low-cost, large-area luminescence applications with air-stabilized electrodes and a versatile fabrication that enables the use of solution processes. Nevertheless, the commercialization of LECs is still encountering many obstacles, such as low electroluminescence (EL) efficiencies of the ionic materials. In this paper, we propose five blue to yellow ionic Ir complexes possessing 4-fluoro-4′-pyrazolyl-(1,1′-biphenyl)-2-carbonitrile (ppfn) as a novel cyclometalating ligand and use them in LECs. In particular, the device within di[4-fluoro-4′-pyrazolyl-(1,1′-biphenyl)-2-carbonitrile]-4,4′-di-tert-butyl-2,2′-bipyridyl iridium(III) hexafluorophosphate (DTBP) shows a remarkable photoluminescence quantum yield (PLQY) of 70%, and by adjusting the emissive-layer thickness, the maximal external quantum efficiency (EQE) reaches 22.15% at 532 nm under the thickness of 0.51 μm, showing the state-of-the-art value for the reported blue-green LECs.

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Section: Resultsmentioning

confidence: 99%

Cationic Ir(III) Complexes with 4-Fluoro-4′-pyrazolyl-(1,1′-biphenyl)-2-carbonitrile as the Cyclometalating Ligand: Synthesis, Characterizations, and Application to Ultrahigh-Efficiency Light-Emitting Electrochemical Cells

Yi,

Lee,

Huang

et al. 2024

Inorg. Chem.

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“…C, H, N analysis: %C calculated 93.46, found 93.07; %H calculated 6.54, found 6.92. Melting point: Reported 68–69 °C, found 70 °C. , …”

Section: Synthesis Detailsmentioning

confidence: 99%

Copper Nanoclusters for Catalytic Carbon–Carbon and Carbon–Nitrogen Bond Formations

Mondal

Basu

Jana

et al. 2022

ACS Appl. Nano Mater.

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Newly synthesized blue-emitting few-atom copper nanoclusters (CuNCs) have been successfully utilized for catalyzing C(sp2)–C(sp2) and C(sp2)–N(sp3) bond formations. Various substituted biphenyls and 2° aromatic amines have been synthesized in good yield using this copper catalyst at facile reaction conditions in dimethyl sulfoxide. The amount of required nanocatalysts is as low as merely 2 mol % for carrying out these reactions. These types of copper nanoclusters are promising as potential and cheap catalysts for replacing conventional metal nanoparticles and heavy-metal-ion-based organic catalysts. The optimized structure of Cu6(GS)2 [GS = C10H16N3O6S] from computational studies revealed the perfect arrangements of Cu atoms in CuNCs and their interactions with stabilizing ligands. It is evident from the structure that some free Cu sites are available in the nanocluster species. These kinds of coordinatively unsaturated sites are highly active toward the catalytic reactions. Matrix-assisted laser desorption ionization–time-of-flight (MALDI–TOF) analysis also supports the computational hypothesis. Interestingly, matrix-assisted laser desorption ionization–time-of-flight mass spectrometry (MALDI–TOF MS) and computational studies revealed the formation of several reaction key intermediates in catalyzing C(sp2)–C(sp2) bond formation.

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“…Bromophenols are versatile starting materials in a carbon-carbon bond coupling reaction [1][2][3][4][5]. They are also important constituents of naturally occurring compounds that possess a range of biological activities [6][7][8][9], such as antioxidant, antimicrobial and anticancer effects.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Monobromination of Phenols with KBr and ZnAl–BrO3−–Layered Double Hydroxides

et al. 2020

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The regioselective mono-bromination of phenols has been successfully developed with KBr and ZnAl–BrO3−–layered double hydroxides (abbreviated as ZnAl–BrO3−–LDHs) as brominating reagents. The para site is much favorable and the ortho site takes the priority if para site is occupied. This reaction featured with excellent regioselectivity, cheap brominating reagents, mild reaction condition, high atom economy, broad substrate scope, and provided an efficient method to synthesize bromophenols.

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Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis

Cited by 16 publications

References 14 publications

Cationic Ir(III) Complexes with 4-Fluoro-4′-pyrazolyl-(1,1′-biphenyl)-2-carbonitrile as the Cyclometalating Ligand: Synthesis, Characterizations, and Application to Ultrahigh-Efficiency Light-Emitting Electrochemical Cells

Cationic Ir(III) Complexes with 4-Fluoro-4′-pyrazolyl-(1,1′-biphenyl)-2-carbonitrile as the Cyclometalating Ligand: Synthesis, Characterizations, and Application to Ultrahigh-Efficiency Light-Emitting Electrochemical Cells

Copper Nanoclusters for Catalytic Carbon–Carbon and Carbon–Nitrogen Bond Formations

Regioselective Monobromination of Phenols with KBr and ZnAl–BrO3−–Layered Double Hydroxides

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