Insights into the General and Efficient Cross McMurry Reactions between Ketones

Duan, Xin-Fang; Zeng, Jing; Lü, Jia-Wei; Zhang, Zhanbin

doi:10.1021/jo061644d

Cited by 146 publications

(108 citation statements)

References 20 publications

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“…Compound 2 was synthesized as a mixture of Z and E isomers via the reaction between propionyl ferrocene and 4-aminobenzophenone, as previously reported [28]. The moderate yield (26%) is consistent with the previously observed low activity of aminobenzophenone in McMurry reactions [29]. The Z and E isomers of 2 could not be separated using preparative HPLC, and thus the mixture of (Z+E)-2 was used in all further experiments.…”

Section: Preparation Of Compoundssupporting

confidence: 73%

The replacement of a phenol group by an aniline or acetanilide group enhances the cytotoxicity of 2-ferrocenyl-1,1-diphenyl-but-l-ene compounds against breast cancer cells

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Zekri

et al. 2009

Journal of Organometallic Chemistry

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a b s t r a c tWe have previously shown that conjugated ferrocenyl p-phenols show strong cytotoxic effects against both the hormone-dependent MCF-7 and hormone-independent MDA-MB-231 breast cancer cell lines, possibly via oxidative quinone methide formation. We now present a series of analogous amine and acetamide compounds: 2-ferrocenyl-1-(4-aminophenyl)-1-phenyl-but-1-ene (Z+E-2), 2-ferrocenyl-1-(4-Nacetylaminophenyl)-1-phenyl-but-1-ene (Z-3), and their corresponding organic molecules 1-(4-aminophenyl)-1,2-bis-phenyl-but-1-ene (Z+E-4) and 1-(4-N-acetamidophenyl)-1,2-bis-phenyl-but-1-ene (Z+E-5). All of the compounds have adequate relative binding affinity values for the estrogen receptor; between 2.8% and 5.7% for ERa, and between 0.18% and 15.5% for ERb, as well as exothermic ligand binding in in silico ER docking experiments. Compounds 2 and 3 show dual estrogenic/cytotoxic activity on the MCF-7 cell line; they are proliferative at low concentrations (0.1 lM) and antiproliferative at high concentrations (10 lM). On the MDA-MB-231 cell line, the ferrocenyl complexes 2 and 3 are antiproliferative with IC 50 values of 0.8 lM for 2 and 0.65 lM for 3, while the purely organic molecules 4 and 5 show no effect. Electrochemical experiments suggest that both 2 and 3 can be transformed to oxidized quinoidtype species, analogous to what had previously been observed for the ferrocene phenols.

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Section: Preparation Of Compoundssupporting

confidence: 73%

The replacement of a phenol group by an aniline or acetanilide group enhances the cytotoxicity of 2-ferrocenyl-1,1-diphenyl-but-l-ene compounds against breast cancer cells

Pigeon

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Zekri

et al. 2009

Journal of Organometallic Chemistry

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“…10,11 CzPATPE was readily obtained by the Pd-catalysed amination of BrmCP with TPENH 2 . Precursors 4-(1,2,2triphenylvinyl)aniline (TPENH 2 ) and 9,9'-(5-bromo-1,3phenylene)bis(9H-carbazole) (BrmCP) were synthesized by known literature procedures.…”

Section: Resultsmentioning

confidence: 99%

The first aggregation-induced emission fluorophore as a solution processed host material in hybrid white organic light-emitting diodes

et al. 2016

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A judicious structure design of bis(3,5-di(9H-carbazol-9-yl)phenyl)amine (CzPA) and 1,1,2,2-tetraphenylethene (TPE) hybrid generates the first aggregation-induced emission (AIE) fluorophore, CzPATPE, as a solution processed host material in hybrid white organic light-emitting diode (OLED). Small molecule CzPATPE has been verified for the amorphous characteristics by a featureless halo in powder X-ray diffraction spectra and a glass transition temperature as high as 180 o C. Fluorescence images indicate that a homogenous thin film of CzPATPE is obtained from a solution drop-casting process. Solution (THF/water) fluorescence spectroscopy study clearly demonstrates a typical AIE property of CzPATPE. Whereas CzPATPE is virtually non-emissive in common organic solvents, thin film photoluminescence (PL) spectroscopy shows that CzPATPE has a strong sky blue emission around 495 nm with a relatively wide full width at half maximum (FWHM) about 95 nm and a reasonable PL quantum yield of 40%. Low temperature time-gated PL spectroscopy identifies CzPATPE's triplet optical gap energy ET ~2.05-2.16 eV, which is barely enough for phosphorescence dopant, tris(2phenylquinoline) iridium (III) (Ir(2-phq)3) (ET ~2.13 eV). CzPATPE is solution processable to be a sky blue emissive host material for orange dopant in the hybrid white OLED, ITO/PEDOT:PSS (65 nm)/CzPATPE:Ir(2-phq)3(99.9:0.1,~40 nm)/TmPyPB(50 nm)/CsF (2 nm)/Al(100 nm). This AIE hybrid white OLED displays white electroluminescence (EL) with colour chromaticity of CIEx,y(0.36, 0.43). Although the maximum EL efficiency is modest 3.4 cd/A or 1.8 lm/W, the white OLED has a colour rendering index (CRI) of 72, which is unusually high considering the orange dopant and two-colour white feature. We attribute such CRI to the relatively large FWHM of CzPATPE.

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“…To implement the one-pot click process for the preparation of two materials, three precursors (TPE-2alkyne, mono-6-azido-CD, and alkyne silica) should be prepared initially. The click precursor TPE-2alkynl (compound 2 ) was prepared by reacting TPE-2OH (synthesized via McMurry coupling reaction according to the reported methods with a yield of 76% [32]) with propargyl bromide in a basic environment and characterized by 1 H-NMR (Figure S2 ESI † ). The precursors mono-6-azido-CD (compound 3 ) and alknyl silica were synthesized following our previous methods [33,34].…”

Section: Resultsmentioning

confidence: 99%

One-Pot Click Access to a Cyclodextrin Dimer-Based Novel Aggregation Induced Emission Sensor and Monomer-Based Chiral Stationary Phase

Zhao

Tang

et al. 2016

Sensors

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A ‘two birds, one stone’ strategy was developed via a one-pot click reaction to simultaneously prepare a novel cyclodextrin (CD) dimer based aggregation induced emission (AIE) sensor (AIE-DCD) and a monomer based chiral stationary phase (CSP-MCD) for chiral high performance liquid chromatography (CHPLC). AIE-DCD was found to afford satisfactory AIE response for specific detection of Zn2+ with a detection limit of 50 nM. CSP-MCD exhibits excellent enantioseparation ability toward dansyl amino acids, where the resolution of dansyl amino leucine reaches 5.43.

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Insights into the General and Efficient Cross McMurry Reactions between Ketones

Cited by 146 publications

References 20 publications

The replacement of a phenol group by an aniline or acetanilide group enhances the cytotoxicity of 2-ferrocenyl-1,1-diphenyl-but-l-ene compounds against breast cancer cells

The replacement of a phenol group by an aniline or acetanilide group enhances the cytotoxicity of 2-ferrocenyl-1,1-diphenyl-but-l-ene compounds against breast cancer cells

The first aggregation-induced emission fluorophore as a solution processed host material in hybrid white organic light-emitting diodes

One-Pot Click Access to a Cyclodextrin Dimer-Based Novel Aggregation Induced Emission Sensor and Monomer-Based Chiral Stationary Phase

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