Functionalized chitosan as a novel support for stabilizing palladium in Suzuki reactions

Dong, Yahao; Bi, Jiajun; Ming, Shujun; Zhang, Shoute; Zhu, Dan; Meng, Di; Li, Tao

doi:10.1016/j.carbpol.2021.117815

Cited by 53 publications

(20 citation statements)

References 60 publications

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“…The target pure product was obtained by column chromatography after removal of organic solvent using a rotary evaporator. All the products are known and their 1 H NMR and 13 C NMR data were in accordance with those reported literature.…”

Section: Procedures For the Pretreatment Of Microcrystalline Cellulosesupporting

confidence: 86%

“…After evaporation of solvent by using a rotary evaporator, the residue was isolated by column chromatography on silica gel to give the desired pure product. All the products are known and their 1 H NMR and 13 C NMR data were identical to those reported in the literature.…”

Section: Procedures For the Pretreatment Of Microcrystalline Cellulosesupporting

confidence: 63%

“…Gas chromatography (GC) was performed on a Shimadzu GCMS-QP2020. 1 H NMR (300 MHz) and 13 C NMR (75 MHz) spectra were obtained with a Bruker Avance instrument with CDCl 3 as solvent and TMS as internal standard. HRMS was determined by using Agilent 6545 Q-TOF MS.…”

Section: Materials and Instrumentationsmentioning

confidence: 99%

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Palladium supported on ethylenediaminetetraacetic acid functionalized cellulose: synthesis, characterization, and its application in carbon–carbon cross-coupling reactions

Zheng

et al. 2022

Cellulose

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Through the esteri cation of cellulose (Cell) with ethylenediaminetetraacetic dianhydride, ethylenediaminetetraacetic acid-functionalized cellulose (Cell-EDTA) was conveniently obtained. Furtherly a novel and e cient Cell-EDTA-supported palladium catalyst (Pd@Cell-EDTA) was easily prepared via coordination of Cell-EDTA with PdCl 2 . The as-prepared Pd@Cell-EDTA was fully characterized by inductively coupled plasma atomic emission spectrometry (ICP-AES), X-ray photoelectron spectroscopy (XPS), Flourier transform infrared spectra (FTIR), energy-dispersive spectroscopy (EDS), scanning electron microscopy, transmission electron microscopy (SEM), thermogravimetric analysis (TGA) and derivative thermogravimetric analysis (DTG) techniques. Then Pd@Cell-EDTA were successfully exerted as catalysts in Suzuki reactions and Sonogashira reactions. Due to the interactions of carboxylic groups, nitrogen atoms, and hydroxyl groups on cellulose, the Pd complex showed excellent activity towards these carbon-carbon cross-coupling reactions. The catalyst recycling experiment for Suzuki model reaction showed that the catalyst can be reused at least ve times without signi cant losing its catalytic performance. The present cellulose-based Pd@Cell-EDTA catalyst offers the salient features of wide application, excellent catalytic activity, good reusability, tolerance of broad scope of substrate, and environmental benign.

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Section: Procedures For the Pretreatment Of Microcrystalline Cellulosesupporting

confidence: 86%

Section: Procedures For the Pretreatment Of Microcrystalline Cellulosesupporting

confidence: 63%

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Palladium supported on ethylenediaminetetraacetic acid functionalized cellulose: synthesis, characterization, and its application in carbon–carbon cross-coupling reactions

Zheng

et al. 2022

Cellulose

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“…Increased MMT addition disrupts the biopolymer plasticizer interactions, increasing the surface's wettability [91]. OCMCS-SB, a stabilizer agent synthesized from chitosan and palladium, was tested for stability during Suzuki reactions and found to be satisfactory, with the possibility of further applications in organic transformations [92]. To increase the efficiency of the solar steam generator, semi-conductive in-situ-polymerized MnO2 nanowire-chitosan hydrogels were vertically stacked in macropore water channels.…”

Section: Other Applicationsmentioning

confidence: 99%

Chitosan: A Sustainable Material for Multifarious Applications

et al. 2022

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Due to the versatility of its features and capabilities, chitosan generated from marine crustacean waste is gaining importance and appeal in a wide variety of applications. It was initially used in pharmaceutical and medical applications due to its antibacterial, biocompatible, and biodegradable properties. However, as the demand for innovative materials with environmentally benign properties has increased, the application range of chitosan has expanded, and it is now used in a variety of everyday applications. The most exciting aspect of the chitosan is its bactericidal properties against pathogens, which are prevalent in contaminated water and cause a variety of human ailments. Apart from antimicrobial and water filtration applications, chitosan is used in dentistry, in water filtration membranes to remove metal ions and some heavy metals from industrial effluents, in microbial fuel cell membranes, and in agriculture to maintain moisture in fruits and leaves. It is also used in skin care products and cosmetics as a moisturizer, in conjunction with fertilizer to boost plant immunity, and as a bi-adhesive for bonding woods and metals. As it has the capacity to increase the life span of food items and raw meat, it is an unavoidable component in food packing and preservation. The numerous applications of chitosan are reviewed in this brief study, as well as the approaches used to incorporate chitosan alongside traditional materials and its effect on the outputs.

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“…Because of the polar nature of C═N, these azomethine undergoes different sorts of reaction such as with Nsulphinyl anilines [12], ketenes [13], Reformatsky reagent [14], and nitrile oxide [15]. Moreover, they can also be utilized as catalysts [16], intermediates in organic synthesis [17], colors [18], shades, chemosensors [19], polymer stablizers [20], consumption inhibitors, and so forth [3]. Lactams (Azetidinone), which are cyclic amides, are one of such compounds that are differently utilized in number of territories.…”

Section: Introductionmentioning

confidence: 99%

Staudinger ketene–imine [2+2] cycloaddition of novel azomethines to synthesize biologically active azetidinone derivatives and their in vitro antimicrobial studies

Kapoor

Rajput

2021

Journal of Heterocyclic Chem

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Since considerable intrigue has been focused on azetidinone (β-lactam) compounds for their wide range antimicrobial activity, the present study focuses on the synthesis of new series of azetidinone compounds. The reaction between the novel azomethine and α-haloester in the presence of Zn impetus and benzene resulted into the formation of desired azetidinone derivative by [2+2] cycloaddition involving imine-ketene. The reaction has also been studied in the presence of diverse Lewis acids such as Zn(OTf) 2 , ZnCl 2 , Cu(OTf) 2 , TiCl 4 , and BF 3 .Et 2 O. The effect of such Lewis acids also enhance the yield of the desired product. Moreover, the structure of the isolated products was also affirmed by spectral analysis (Fourier-transform infrared [FT-IR] spectroscopy, proton nuclear magnetic resonance [ 1 H NMR], carbon-13 nuclear magnetic resonance [ 13 C NMR], and high-resolution mass spectrometry [HRMS]). Furthermore, the antibacterial activity of synthesized compounds has been screened in vitro against different pathogenic bacterial and fungus species.Inspection of the results uncovered that all of the newly synthesized compounds individually display varying degrees of inhibitory impacts on the development of the tested bacterial species, thus, they might be considered as medication possibility for bacterial pathogens. The azomethine exhibited an expansive range of antibacterial activity against Gram-negative Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, and Acinetobacter baumannii and Gram-positive Staphylococcus aureus bacterial strains and antifungal activity against Candida albicans, Candida tropicalis, and Candida parapsilosis bacterial strain. The result demonstrated that the β-lactam subordinates have good antibacterial and antifungal activities on microscopic organisms.

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Functionalized chitosan as a novel support for stabilizing palladium in Suzuki reactions

Cited by 53 publications

References 60 publications

Palladium supported on ethylenediaminetetraacetic acid functionalized cellulose: synthesis, characterization, and its application in carbon–carbon cross-coupling reactions

Palladium supported on ethylenediaminetetraacetic acid functionalized cellulose: synthesis, characterization, and its application in carbon–carbon cross-coupling reactions

Chitosan: A Sustainable Material for Multifarious Applications

Staudinger ketene–imine [2+2] cycloaddition of novel azomethines to synthesize biologically active azetidinone derivatives and their in vitro antimicrobial studies

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