Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions

Saba, Sumbal; Botteselle, Giancarlo V.; Godoi, Marcelo; Frizon, Tiago Elias Allievi; Galetto, Fábio Z.; Rafique, Jamal; Braga, Antônio L.

doi:10.3390/molecules22081367

Cited by 50 publications

(25 citation statements)

References 70 publications

(81 reference statements)

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“…In relation to our continuous interest in the developing new synthetic methodologies, as well as in the design of eco‐friendly processes,–, herein we report, for the first time, the use of the ytterbium triflate/sodium dodecyl sulfate (SDS) as an efficient and recyclable catalyst to promote the Friedel‐Crafts alkylation between indoles and aldehydes, which tolerate aqueous media. In comparison with previous reports, this greener approach is energy efficiency, which operates under ambient temperature, involves a recyclable catalyst and a sustainable solvent (water).…”

Section: Introductionmentioning

confidence: 99%

Ytterbium (III) triflate/Sodium Dodecyl Sulfate: A Versatile Recyclable and Water‐Tolerant Catalyst for the Synthesis of Bis(indolyl)methanes (BIMs)

et al. 2018

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Herein, we report the application of ytterbium(III) triflate as an efficient and versatile catalyst to synthesize bis(indolyl)methanes. The coupled products were obtained in good to excellent yields under mild reaction conditions and in a short reaction time. The catalyst was readily recovered from the reaction mixture and could be reused without any loss of activity. Moreover, the study of photophysical properties of bis(indolyl) methanes was also performed.

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Section: Introductionmentioning

confidence: 99%

Ytterbium (III) triflate/Sodium Dodecyl Sulfate: A Versatile Recyclable and Water‐Tolerant Catalyst for the Synthesis of Bis(indolyl)methanes (BIMs)

et al. 2018

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“…Diphenyl diselenide ((PhSe)2) is other organoselenium compound with GPx-like activity (Figure 1) [23]. By considering the biological roles of these compounds, development of new and efficient routes for the synthesis of organoselenides is a tempting research area [12,24,25]. Therefore, as an additional step of the ongoing efforts aiming the design of novel organoselenides and medicinal chemistry [26][27][28], present study reports the synthesis of novel aromatic selenocyanates, comprising a second generation of chalcogenide esters.…”

Section: Introductionmentioning

confidence: 98%

Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress

Frizon¹,

Cararo²,

Saba³

et al. 2020

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Herein we report the synthesis of novel selenocyanates and assessment of their effect on the oxidative challenge elicited by hydrogen peroxide (H2O2) in cultured mouse neurons. First, α-methylene-β-hydroxy esters were prepared as precursors of allylic bromides. A reaction involving the generated bromides and sodium selenocyanate was conducted to produce the desired selenocyanates (3a-f). We next prepared cultures of neurons from 7-day-old-mice (n = 36). H2O2 (10⁻5 M) was added into the culture flasks as an oxidative stress inducer, alone or combined with one of each designed compounds. PhSe)2 was used as positive control. It was carried out assessment of lipid (thiobarbituric acid reactive species, 4-hydroxy-2’-nonenal, 8-isoprostane), DNA (8-hydroxy-2’-deoxyguanosine) and protein (carbonyl) modification parameters. Finally, catalase and superoxide dismutase activities were also evaluated. Among the compounds, 3b, 3d and 3f exhibited the most pronounced pattern of antioxidant activity, similar to (PhSe)2. These novel aromatic selenocyanates could be promising to be tried in most sophisticated in vitro studies or even at preclinical level.

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“…As part of our continued involvement in the chemistry of Nheterocycles (Saba et al, 2015(Saba et al, , 2016(Saba et al, , 2017(Saba et al, , 2018(Saba et al, , 2020Rafique et al, 2016Rafique et al, , 2018aSilva et al, 2017;Bettanin et al, 2018;Peterle et al, 2018;Rodigues et al, 2018;Tornquist et al, 2018;Meirinho et al, 2019;Neto et al, 2020;Scheide et al, 2020) and material sciences (Frizon et al, 2014(Frizon et al, , 2015(Frizon et al, , 2016(Frizon et al, , 2018Bo et al, 2016Bo et al, , 2018Westrup et al, 2016;Matzkeit et al, 2018;Regis et al, 2018), herein, we report the synthesis and characterization of BOX derivatives containing electrondonor groups (alkylated tetrazole rings) connected to the 2,1,3-BOX group as an electron-acceptor unit. In addition, thermal, electrochemical, and theoretical predictions were made and photophysical analysis was performed to study the stability, likely geometry, and luminescence properties of these compounds in their ground and excited electronic states.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

et al. 2020

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Herein, we report the synthesis and characterization of fluorophores containing a 2,1,3-benzoxadiazole unit associated with a π-conjugated system (D-π-A-π-D). These new fluorophores in solution exhibited an absorption maximum at around ∼419 nm (visible region), as expected for electronic transitions of the π-π * type (ε ∼2.7 × 10 7 L mol −1 cm −1), and strong solvent-dependent fluorescence emission (Φ FL ∼0.5) located in the bluish-green region. The Stokes' shift of these compounds is ca. 3,779 cm −1 , which was attributed to an intramolecular charge transfer (ICT) state. In CHCl 3 solution, the compounds exhibited longer and shorter lifetimes, which was attributed to the emission of monomeric and aggregated molecules, respectively. Density functional theory was used to model the electronic structure of the compounds 9a-d in their excited and ground electronic states. The simulated emission spectra are consistent with the experimental results, with different solvents leading to a shift in the emission peak and the attribution of a π-π * state with the characteristics of a charge transfer excitation. The thermal properties were analyzed by thermogravimetric analysis, and a high maximum degradation rate occurred at around 300 • C. Electrochemical studies were also performed in order to determine the band gaps of the molecules. The electrochemical band gaps (2.48-2.70 eV) showed strong correlations with the optical band gaps (2.64-2.67 eV).

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Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions

Cited by 50 publications

References 70 publications

Ytterbium (III) triflate/Sodium Dodecyl Sulfate: A Versatile Recyclable and Water‐Tolerant Catalyst for the Synthesis of Bis(indolyl)methanes (BIMs)

Ytterbium (III) triflate/Sodium Dodecyl Sulfate: A Versatile Recyclable and Water‐Tolerant Catalyst for the Synthesis of Bis(indolyl)methanes (BIMs)

Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

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