653-37-2Relevant academic research and scientific papers
Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents
Antony, Jesna,Mathai, Sindhu,Natarajan, Rakesh,P. Musthafa, Sumi,Rappai, John P.,S. Devaky, Karakkattu
supporting information, (2022/02/25)
We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.
Efficient aerial oxidation of different types of alcohols using ZnO nanoparticle–MnCO3-graphene oxide composites
Adil, Syed Farooq,Assal, Mohamed E.,Shaik, Mohammed Rafi,Kuniyil, Mufsir,Hashmi, Azhar,Khan, Mujeeb,Khan, Aslam,Tahir, Muhammad Nawaz,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.
, (2020/06/08)
Graphene–metal nanocomposites have been found to remarkably enhance the catalytic performance of metal nanoparticle-based catalysts. In continuation of our previous report, in which highly reduced graphene oxide (HRG)-based nanocomposites were synthesized and evaluated, we present nanocomposites of graphene oxide (GRO) and ZnO nanoparticle-doped MnCO3 ([ZnO–MnCO3/(1%)GRO]) synthesized via a facile, straightforward co-precipitation technique. Interestingly, it was noticed that the incorporation of GRO in the catalytic system could noticeably improve the catalytic efficiency compared to a catalyst (ZnO–MnCO3) without GRO, for aerial oxidation of benzyl alcohol (BzOH) employing O2 as a nature-friendly oxidant under base-free conditions. The impacts of various reaction factors were thoroughly explored to optimize reaction conditions using oxidation of BzOH to benzaldehyde (BzH) as a model substrate. The catalysts were characterized using X-ray diffraction, thermogravimetric analysis, Fourier transform infrared spectroscopy, field-emission scanning electron microscopy, Energy dispersive X-ray spectroscopy (EDX), Brunauer-Emmett-Teller (BET), and Raman spectroscopy. The (1%)ZnO–MnCO3/(1%)GRO exhibited significant specific activity (67 mmol.g?1.hr?1) with full convversion of BzOH and >99% BzH selectivity within just 6 min. The catalytic efficiency of the (1%)ZnO–MnCO3/(1%)GRO nanocomposite was significantly better than the (1%)ZnO–MnCO3/(1%)HRG and (1%)ZnO–MnCO3 catalysts, presumably due to the existence of oxygen-possessing groups on the GRO surface and as well as a very high surface area that could have been instrumental in uniformly dispersing the active sites of the catalyst, i.e., ZnO–MnCO3. Under optimum circumstances, various kinds of alcohols were selectively transformed to respective carbonyls with full convertibility over the (1%)ZnO–MnCO3/(1%)GRO catalyst. Furthermore, the highly effective (1%)ZnO–MnCO3/(1%)GRO catalyst could be successfully reused and recycled over five consecutive runs with a marginal reduction in its performance and selectivity.
Reactions of Polyfluoroaromatic Organozinc Compounds with Oxalyl Chloride in DMF. Synthesis of Polyfluoroaromatic Aldehydes
Vinogradov,Platonov
, p. 2264 - 2272 (2021/02/12)
Abstract: The reaction of polyfluoroaromatic organozinc compounds with oxalyl chloride in DMF proceeds involving the Vilsmeier–Haack reagent with the formation of polyfluoroaromatic aldehydes as the major products. The use of CuI makes it possible to incr
Preparation method of pentafluorobenzaldehyde
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Paragraph 0225-0226, (2017/06/02)
The invention relates to a preparation method of pentafluorobenzaldehyde, and belongs to the field of fine chemical product preparation. According to the preparation method, catalyst Ni-Al alloy, pentafluorobenzonitrile, and formic acid are subjected to reaction in water to prepare pentafluorobenzaldehyde. Ni-Al alloy is adopted, formic acid and water are taken as reducing agents, and pentafluorobenzaldehyde is prepared via reduction of pentafluorobenzonitrile. The preparation method is capable of realizing direction reduction of pentafluorobenzonitrile into pentafluorobenzaldehyde, so that reaction steps are reduced, generation of waste is reduced, production cost is reduced, and environmental pollution is reduced.
Synthesis and Comparative Catalytic Study of Zirconia–MnCO3 or –Mn2O3 for the Oxidation of Benzylic Alcohols
Assal, Mohamed E.,Kuniyil, Mufsir,Khan, Mujeeb,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.,Tremel, Wolfgang,Nawaz Tahir, Muhammad,Adil, Syed Farooq
, p. 112 - 120 (2017/02/10)
We report on the synthesis of the zirconia–manganese carbonate ZrOx(x %)–MnCO3 catalyst (where x=1–7) that, upon calcination at 500 °C, is converted to zirconia–manganese oxide ZrOx(x %)–Mn2O3. We also present a comparative study of the catalytic performance of the both catalysts for the oxidation of benzylic alcohol to corresponding aldehydes by using molecular oxygen as the oxidizing agent. ZrOx(x %)–MnCO3 was prepared through co-precipitation by varying the amounts of Zr(NO3)4 (w/w %) in Mn(NO3)2. The morphology, composition, and crystallinity of the as-synthesized product and the catalysts prepared upon calcination were studied by using scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, and powder X-ray diffraction. The surface areas of the catalysts [133.58 m2 g?1 for ZrOx(1 %)–MnCO3 and 17.48 m2 g?1 for ZrOx(1 %)–Mn2O3] were determined by using the Brunauer–Emmett–Teller method, and the thermal stability was assessed by using thermal gravimetric analysis. The catalyst with composition ZrOx(1 %)–MnCO3 pre-calcined at 300 °C exhibited excellent specific activity (48.00 mmolg?1 h?1) with complete conversion within approximately 5 min and catalyst cyclability up to six times without any significant loss in activity. The specific activity, turnover number and turnover frequency achieved is the highest so far (to the best of our knowledge) compared to the previously reported catalysts used for the oxidation of benzyl alcohol. The catalyst showed selectivity for aromatic alcohols over aliphatic alcohols.
Synthesis, Characterization, and Relative Study on the Catalytic Activity of Zinc Oxide Nanoparticles Doped MnCO3, -MnO2, and -Mn2O3 Nanocomposites for Aerial Oxidation of Alcohols
Assal, Mohamed E.,Kuniyil, Mufsir,Shaik, Mohammed Rafi,Khan, Mujeeb,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.,Adil, Syed Farooq
, (2017/08/04)
Zinc oxide nanoparticles doped manganese carbonate catalysts [X% ZnOx-MnCO3] (where X = 0-7) were prepared via a facile and straightforward coprecipitation procedure, which upon different calcination treatments yields different manganese oxides, that is, [X% ZnOx-MnO2] and [X% ZnOx-Mn2O3]. A comparative catalytic study was conducted to evaluate the catalytic efficiency between carbonates and oxides for the selective oxidation of secondary alcohols to corresponding ketones using molecular oxygen as a green oxidizing agent without using any additives or bases. The prepared catalysts were characterized by different techniques such as SEM, EDX, XRD, TEM, TGA, BET, and FTIR spectroscopy. The 1% ZnOx-MnCO3 calcined at 300°C exhibited the best catalytic performance and possessed highest surface area, suggesting that the calcination temperature and surface area play a significant role in the alcohol oxidation. The 1% ZnOx-MnCO3 catalyst exhibited superior catalytic performance and selectivity in the aerial oxidation of 1-phenylethanol, where 100% alcohol conversion and more than 99% product selectivity were obtained in only 5 min with superior specific activity (48 mmol·g-1·h-1) and 390.6 turnover frequency (TOF). The specific activity obtained is the highest so far (to the best of our knowledge) compared to the catalysts already reported in the literatures used for the oxidation of 1-phenylethanol. It was found that ZnOx nanoparticles play an essential role in enhancing the catalytic efficiency for the selective oxidation of alcohols. The scope of the oxidation process is extended to different types of alcohols. A variety of primary, benzylic, aliphatic, allylic, and heteroaromatic alcohols were selectively oxidized into their corresponding carbonyls with 100% convertibility without overoxidation to the carboxylic acids under base-free conditions.
A highly reduced graphene oxide/ZrOx-MnCO3 or -Mn2O3 nanocomposite as an efficient catalyst for selective aerial oxidation of benzylic alcohols
Assal, Mohamed E.,Shaik, Mohammed Rafi,Kuniyil, Mufsir,Khan, Mujeeb,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.,Khan, Sohail M. A.,Tremel, Wolfgang,Tahir, Muhammad Nawaz,Adil, Syed Farooq
, p. 55336 - 55349 (2018/04/05)
Highly reduced graphene oxide (HRG) nanocomposites of manganese carbonate doped with (1%) zirconia (ZrOx) nanoparticles [ZrOx(1%)-MnCO3/(X%)HRG (where X = 0-7)] were prepared employing a facile coprecipitation method in which the percentage of HRG was varied. The resulting nanocomposite was calcined at 300°C. Further calcination of the catalyst at 500°C resulted in the conversion of manganese carbonate to manganese oxide [ZrOx(1%)-Mn2O3/(X%)HRG]. The effect of the inclusion of HRG on the catalytic activity along with its comparative performance between carbonates and their respective oxides was studied for the liquid-phase selective oxidation of benzylic alcohols into corresponding aldehydes using molecular oxygen as the eco-friendly oxidizing agent without adding any external additives or bases. The influence of different parameters such as different percentages of HRG, reaction times, calcination temperatures, catalyst dosages and reaction temperatures have also been systematically studied in order to optimize the catalyst composition and reaction conditions. The inclusion of HRG as a dopant remarkably enhanced the catalytic efficiency of ZrOx-MnCO3 nanocatalysts for the aerobic oxidation of alcohols. The as-prepared catalysts were characterized by scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), powder X-ray diffraction (XRD), thermal gravimetric analysis (TGA), Brunauer-Emmett-Teller (BET) surface area analysis, Raman spectroscopy and Fourier transform infrared spectroscopy (FT-IR). The catalyst with composition ZrOx(1%)-MnCO3/(1%)HRG obtained by calcination at 300°C exhibited excellent specific activity (60.0 mmol g-1 h-1) with 100% benzyl alcohol conversion and more than 99% product selectivity within an extremely short time (4 min). The same catalyst is employed for the oxidation of a wide range of substituted benzylic and aliphatic alcohols. The catalyst i.e. ZrOx(1%)-MnCO3/(1%)HRG calcined at 300°C yielded corresponding aldehydes with complete convertibility and selectivity in short reaction times under mild conditions whereas the as-prepared catalyst exhibited high selectivity for aromatic alcohols over aliphatic alcohols. The catalyst was recycled and reused at least five times without any obvious loss in its activity or selectivity.
Synthesis of Aldehydes by Organocatalytic Formylation Reactions of Boronic Acids with Glyoxylic Acid
Huang, He,Yu, Chenguang,Li, Xiangmin,Zhang, Yongqiang,Zhang, Yueteng,Chen, Xiaobei,Mariano, Patrick S.,Xie, Hexin,Wang, Wei
supporting information, p. 8201 - 8205 (2017/06/30)
Reported herein is a conceptually novel organocatalytic strategy for the formylation of boronic acids. New reactivity is engineered into the α-amino-acid-forming Petasis reaction occurring between aryl boronic acids, amines, and glyoxylic acids to prepare aldehydes. The operational simplicity of the process and its ability to generate structurally diverse and valued aryl, heteroaryl, and α,β-unsaturated aldehydes containing a wide array of functional groups, demonstrates the practical utility of the new synthetic strategy.
Laccase-Mediator System for Alcohol Oxidation to Carbonyls or Carboxylic Acids: Toward a Sustainable Synthesis of Profens
Galletti, Paola,Pori, Matteo,Funiciello, Federica,Soldati, Roberto,Ballardini, Alberto,Giacomini, Daria
, p. 2684 - 2689 (2016/12/23)
By combining two green and efficient catalysts, such as the commercially available enzyme laccase from Trametes versicolor and the stable free radical 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), the oxidation in water of some primary alcohols to the corresponding carboxylic acids or aldehydes and of selected secondary alcohols to ketones can be accomplished. The range of applicability of bio-oxidation is widened by applying the optimized protocol to the oxidation of enantiomerically pure 2-arylpropanols (profenols) into the corresponding 2-arylpropionic acids (profens), in high yields and with complete retention of configuration.
Hypervalent iodine/TEMPO-mediated oxidation in flow systems: A fast and efficient protocol for alcohol oxidation
Ambreen, Nida,Kumar, Ravi,Wirth, Thomas
, p. 1437 - 1442 (2013/08/23)
Hypervalent iodine(III)/TEMPO-mediated oxidation of various aliphatic, aromatic and allylic alcohols to their corresponding carbonyl compounds was successfully achieved by using microreactor technology. This method can be used as an alternative for the oxidation of various alcohols achieving excellent yields and selectivities in significantly shortened reaction times.
