ChemInform Abstract: Chemoselective Reaction of Malononitrile with Imine‐ones and Antifungal Potential of Products.

Sidhu, A. S.; Sharma, J. R.; Rai, Mangat

doi:10.1002/chin.201024075

Cited by 6 publications

(6 citation statements)

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“…The catalytic behavior of Cu/ZIF-8(H 2 ) was investigated in a stepwise process coupling benzyl alcohol oxidation with the Knoevenagel reaction, an important C–C coupling reaction widely used in the synthesis of fine chemicals (Scheme ). This “one-pot” process is expected to enhance the sustainability of the synthesis of benzylidene malononitrile, a highly valuable molecule regarding its role as molecular building block for the construction of various nitrogenous heterocycles with versatile biological activities. , …”

Section: Resultsmentioning

confidence: 99%

“…29 This "one-pot" process is expected to enhance the sustainability of the synthesis of benzylidene malononitrile, a highly valuable molecule regarding its role as molecular building block for the construction of various nitrogenous heterocycles with versatile biological activities. 30,31 The rational for this approach relies on the fact that, in addition to the Cu sites responsible for the alcohol oxidation, the Cu/ZIF-8(H 2 )/TEMPO/DMA system also contains two types of chemical basic sites that were recently reported to efficiently catalyze the Knoevenagel reaction: (i) the basic Nmoieties of the ZIF-8 framework 32 and (ii) DMAP. 33 Here, both ZIF-8 and DMAP were first independently tested as catalysts for the Knoevenagel condensation of benzaldehyde with malononitrile under the optimized conditions of benzyl alcohol oxidation set before.…”

Section: Stepwise Benzyl Alcohol Oxidation and Knoevenagel Condensationmentioning

confidence: 99%

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Copper Nanoparticles Supported on ZIF-8: Comparison of Cu(II) Reduction Processes and Application as Benzyl Alcohol Oxidation Catalysts

Zan,

Ben Romdhane,

Miche

et al. 2023

ACS Appl. Mater. Interfaces

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We report the synthesis of a stable heterogeneous catalyst based on copper metal nanoparticles with oxidized surface supported on ZIF-8 for the oxidation of benzyl alcohol under mild temperature and using air as a sustainable oxygen source as well as for the implementation of the tandem “one-pot” catalytic system allowing the sustainable synthesis of benzylidene malononitrile. The influence of the reduction process applied to form the nanoparticle upon the catalyst texture and its performances was extensively examined. After ZIF-8 impregnation with a copper chloride precursor, the reduction of cupric ions into Cu0 nanoparticles was carried out according to two procedures: (i) by soaking the solid into a solution of NaBH4 and (ii) by submitting it to a flow of gaseous H2 at 340 °C. The in-depth physicochemical characterization and comparison of the resulting two types of Cu/ZIF-8 materials reveal significant differences: the reduction with NaBH4 led to the formation of 16 nm sized Cu0 nanoparticles (NP) mainly localized on the external surface of the ZIF-8 crystals together with ZnO nanocrystallites, while the reduction under H2 flow resulted in Cu0 nanoparticles with a mean size of 22 nm embedded within the bulk of ZIF-8 crystals. More, when NaBH4 was used to reduce cupric ions, ZnO particles were highlighted by high-resolution microcospy imaging. Formation of ZnO impurities was confirmed by the photoluminescence analysis of ZIF-8 after NaBH4 treatment. In contrast, ZnO was not detected on ZIF-8 treated with H2. Both types of Cu0 NPs supported on ZIF-8 were found to be active as catalysts toward the aerobic oxidation of benzyl alcohol under moderate temperature (T < 80 °C) and using air as a sustainable O2 source. Benzaldehyde yield of 66% and selectivity superior to 90% were obtained with the Cu/ZIF-8 catalyst prepared under H2 flow after 24 h under these conditions. The same material could be recycled 5 times without loss of activity, unlike the catalysts synthesized with NaBH4, as a result of the leaching of the surface copper NPs over the consecutive catalytic cycles. Finally, the most stable catalyst was successfully implemented in a tandem “one-pot” catalytic system associating benzyl alcohol oxidation and Knoevenagel condensation to synthesize benzylidene malononitrile.

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Section: Resultsmentioning

confidence: 99%

Section: Stepwise Benzyl Alcohol Oxidation and Knoevenagel Condensationmentioning

confidence: 99%

Copper Nanoparticles Supported on ZIF-8: Comparison of Cu(II) Reduction Processes and Application as Benzyl Alcohol Oxidation Catalysts

Zan,

Ben Romdhane,

Miche

et al. 2023

ACS Appl. Mater. Interfaces

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“…The afforded compounds have found promising antifungal activities. [36] have assembled the chemoselective elimination of malononitrile derivatives. [37] have formulated pyrrolo [2,3- …”

Section: 5mentioning

confidence: 99%