Photoinduced one-pot synthesis of hydroxamic acids from aldehydes through in-situ generated silver nanoclusters

Mohamed, Yasser Mahmoud A.; Attia, Yasser A.; Solum, Eirik Johansson

doi:10.1007/s11164-018-3549-z

Cited by 12 publications

(2 citation statements)

References 46 publications

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“…Nowadays, this method is seldomly used, because of the difficulty to remove the benzenesulfinic acid that is formed and its low yields. To date, various methods for the preparation of hydroxamic acids have been developed, including the reaction of nitroarenes and nitrosoarenes with aldehydes, [9b,e] the oxidative amidation of alcohols, [9g] the utilization of Ag nanoclusters, [9i] the direct transformation of aldehydes to hydroxamic acids via N ‐hydroxysuccinimide ester formation, [9f] the hydroacylation of dialkyl azodicarboxylates in the presence of phenylglyoxylic acid [9h] and the reaction of activated carboxylic acids, acyl halides or esters with O ‐protected, N , O ‐protected [9a,d] and unprotected hydroxylamines, [9c] which consists the most common approach for the synthesis of hydroxamic acids (Scheme 2, B2 ). However, these synthetic approaches often require drastic conditions, long reaction times, the use of expensive reagents and present difficulties in the product isolation.…”

Section: Introductionmentioning

confidence: 99%

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

Nikitas

Apostolopoulou

Skolia

et al. 2021

Chemistry A European J

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A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

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Section: Introductionmentioning

confidence: 99%

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

Nikitas

Apostolopoulou

Skolia

et al. 2021

Chemistry A European J

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“…Hence the investigation of innovative approach for catalytic removal of CO through oxidation process along with transformation of para-nitophenol (PNP), which is most toxic organic pollutant in one protocol is highly demanded. Hence, based on our previous studies on the photocatalytic transformation reactions [6][7][8][9] and the previous investigation on the reduction of PNP to high valued PAP and paracetamol, [10] we came in this study to develop an efficient detoxification/transformation approach.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Modified TiO₂/MWCNTs for Efficient Carbon Capture and Photocatalytic Reduction of Nitro‐aromatic Derivatives

et al. 2023

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In this study, modified TiO2 nanocomposites with the noble metal (Ag or Pd) followed by dispersion on multiwall carbon nanotubes (MWCNT) were synthesized and applied in the photocatalytic oxidation of CO at room temperature in the absence of oxygen. The results revealed that the highest active photocatalyst was Pd/TiO2/MWCNT towards CO and p‐nitrophenol (PNP) conversion. The reaction was dependent on the catalyst loading, concentration of tert‐butyl ammonium bromide (TBAB) as co‐catalyst and the reaction time as well as the temperature of their reduction. It was found that the optimal condition for PNP transformed into p‐aminophenol (PAP) and formic acid (HCOOH) was the use of 0.05 wt % of Pd/TiO2/MWCNT nanocatalyst, 2 mol % of TBAB under visible light irradiation condition at room temperature after 1 hour. The as‐prepared photocatalysts were fully characterized using Scanning electron microscope (SEM‐EDX), high resolution transmission electron microscope (HR‐TEM), X‐ray diffraction (XRD) and Brunauer‐Emmett‐Teller (BET). In addition, the band gaps of TiO2 nanoparticles, TiO2/MWCNT and Ag‐ or Pd‐modified TiO2/MWCNT nanocomposites were calculated from diffuse reflectance spectroscopic (DRS) analysis, ensuring the best photocatalytic efficiency. This approach is significantly beneficial for development of new generation of detoxification/transformation catalysts. The probable mechanism of photo‐oxidation of CO by H2O was postulated.

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The influence of ultrasonic irradiation on catalytic performance of ZnO nanoparticles toward the synthesis of chiral 1‐substituted‐1H‐tetrazolederivatives from α‐amino acid ethyl esters

Mohamed

Attia

2020

Applied Organom Chemis

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In this work, a simple and greener protocol for the synthesis of 1‐substituted 1H‐tetrazole derived from α‐amino acid ethyl esters was demonstrated in the presence of zinc oxide nanoparticles (ZnO NPs) under conventional conditions, with heating (at 60 and 80°C and under reflux) compared with ultrasonic. The effect of solvent was investigated to reveal that the solvent system CH3CN/H2O was optimum to obtain 1‐substituted 1H‐tetrazole in high yield. In addition, the effect of irradiation power was studied, which showed that the yield of the reaction was improved at 200 W and the reaction time was shortened to be 30 min. Also, an improvement in the rate of the reaction and the yield of the products was observed when reactions were carried out under sonication conditions in the presence of ZnO NPs compared with conventional methods using various zinc salts as catalysts. The yields of tetrazole compounds 2a–i under sonication were determined (88–96%). Furthermore, the investigated heterogeneous catalytic system was recycled and reused for five runs with significant production of tetrazole 2a as a model target compound in excellent yields at each reaction cycle. In general, the investigated synthetic strategy for the heterocyclization of α‐amino acid ethyl ester derivatives to 1‐substituted 1H‐tetrazoles was in agreement with the green chemistry point of view.

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Photoinduced one-pot synthesis of hydroxamic acids from aldehydes through in-situ generated silver nanoclusters

Cited by 12 publications

References 46 publications

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

Palladium‐Modified TiO₂/MWCNTs for Efficient Carbon Capture and Photocatalytic Reduction of Nitro‐aromatic Derivatives

The influence of ultrasonic irradiation on catalytic performance of ZnO nanoparticles toward the synthesis of chiral 1‐substituted‐1H‐tetrazolederivatives from α‐amino acid ethyl esters

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Photoinduced one-pot synthesis of hydroxamic acids from aldehydes through in-situ generated silver nanoclusters

Cited by 12 publications

References 46 publications

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

Palladium‐Modified TiO2/MWCNTs for Efficient Carbon Capture and Photocatalytic Reduction of Nitro‐aromatic Derivatives

The influence of ultrasonic irradiation on catalytic performance of ZnO nanoparticles toward the synthesis of chiral 1‐substituted‐1H‐tetrazolederivatives from α‐amino acid ethyl esters

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Palladium‐Modified TiO₂/MWCNTs for Efficient Carbon Capture and Photocatalytic Reduction of Nitro‐aromatic Derivatives