Synthesis of new Pro-PYE ligands as co-catalysts toward Pd-catalyzed Heck–Mizoroki cross coupling reactions

Munir, Naima; Masood, Sara; Liaqat, Faroha; Tahir, Muhammad Nawaz; Yousuf, Sammer; Kalsoom, Saima; Mughal, Ehsan Ullah; Sumrra, Sajjad Hussain; Maalik, Aneela; Zafar, Muhammad

doi:10.1039/c9ra07912b

Cited by 10 publications

(5 citation statements)

References 49 publications

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“…On the basis of surface area studies and electronic descriptor calculations, it is confirmed that both FBM and OBM have the ability to extract Pb from water and that OBM is more suitable for capturing Pb as compared to FBM. 53 Molecular descriptor data are given in Table S3.…”

Section: Solubility and Viscosities Of Polyimidesmentioning

confidence: 99%

Synthesis of Sulfonated Copolyimides by Thermal Imidization for Efficient Lead Ion Adsorption from Aqueous Media

Manzoor

Kalsoom

Khan

et al. 2022

ACS Appl. Polym. Mater.

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Thermally stable, high performance sulfonated copolyimide adsorbents [OBM (ODPA+BDSA•TEA+MDA) and FBM (6FDA+BDSA•TEA+MDA)] having excellent adsorption ability were prepared via a two-step thermal imidization reaction. By the introduction of hydrophilic sulfonic acid groups into the polyimide backbone, the material's hydrophilicity was improved. The anionic sulfonate group bears strong affinity toward heavy metal ions. Improvement in polymer hydrophilicity enhances the heavy metal ion adsorption capacity due to feasible access to adsorption sites. Atomic absorption spectroscopy (AAS) was employed for heavy metal ion adsorption studies. In addition, quantum chemistry calculations using Molecular Operating Environment (MOE) software were performed, to scrutinize the experimental results for molecular surface studies. A good correlation was observed between computational and experimental findings. OBM was demonstrated to be more effective for Pb(II) removal from aqueous media with a higher q e and percent removal as compared to FBM. The synthesized sulfonated copolyimides are potential adsorbents for heavy metal ions.

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Section: Solubility and Viscosities Of Polyimidesmentioning

confidence: 99%

Synthesis of Sulfonated Copolyimides by Thermal Imidization for Efficient Lead Ion Adsorption from Aqueous Media

Manzoor

Kalsoom

Khan

et al. 2022

ACS Appl. Polym. Mater.

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“…48 A series of in situ formed Pd catalysts with bis PYA ligands with the two PYA units bridged by cyclohexyl, pyridyl, and ethyl linkers display higher activity in the Mizoroki−Heck cross-coupling reaction under slightly milder conditions (up to 98% in 6 h; 130 °C, DMF, 0.01 mol % Pd). 86 While the exact bonding of the ligand to the palladium center is not known, the in situ formed catalyst succeeds in the olefination of a range of iodo-, bromo-, and even chlorobenzenes with >70% yield. Moreover, the rhodium(I) complex [RhCl(COD)( p-ph PYA)] (COD = cyclooctadiene) catalyzes the C−N bond crosscoupling between anilines and pyridinium amines to form secondary bis-aryl amines.…”

Section: ■ C−c Bond Formation Catalysismentioning

confidence: 99%

Pyridylidene Amines and Amides: Donor-Flexible Ligands for Catalysis

Race

Albrecht

2023

ACS Catal.

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Ligands with flexible donor properties exhibit the unique ability to transition within the continuum of neutral (L-type) and anionic (X-type) metal bonding in response to their local electronic environment. This flexibility stabilizes transition-metal complexes in unparalleled ways and facilitates catalytic turnovers, especially when the catalytic cycle features the active metal center in different oxidation states. Pyridylidene amines (PYEs) and pyridylidene amides (PYAs) are examples of nitrogenbased donor-flexible ligands. In the past decade, the application of PYE and PYA ligands in transition-metal catalysis has been growing, to now include reactions such as hydrogen transfer reactions, water oxidation, and CO 2 utilization, among many others. Here we provide an overview of these powerful ligands, including their synthesis, their donor properties, and in particular their catalytic application�highlighting the key ligand features that impart high activity, as well as the wide potential of this rather underexplored ligand system for diverse catalytic applications.

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“…29 A few publications report the use of PYE ligands in catalysis. Douthwaite et al have shown that Pd(PYE) is analogous to Pd(NHC), and then Munir et al 30 reported Pd(PYE)-catalyzed Heck-Mizoroki cross coupling. Separation of charges allowed the modulate of catalytic activity in Ru complexes by changing the solvent polarity: both catalytic oxidation 31,32 and reduction 32 were dependent on polar cosolvent.…”

Section: Scheme 2 Previous Work On the Nqa Ligand's Donor Properties ...mentioning

confidence: 99%

Monoanionic Quasi-Imido Ligands Based on 1-Methyl-4-Iminopyridine and Complexes with the Main Group Elements Mg, Al and Zn.

Semeniuchenko

Johnson

2022

Preprint

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The synthesis of a new class monoanionic nitrogen donor ligands based on (1-methylpyridin-4(1H)-ylidene)amide, abbreviated MQI (monoanionic quasi imide) and it chemistry with main group elements is reported. The electronic structure of the ligand allows delocalization of positive charge onto the N-heterocycle, which is accompanied by aromatization. The unsubstituted MQI ligand was found to form insoluble intractable products on reaction with non-transition metal alkyls, thus substituents were introduced to increase solubility and stability of those complexes and enable their study. The precursors 3,5-bis(3,5-dimethylphenyl)-1-methylpyridin-4(1H)-imine [MQIMe]H and 3,5-bis(3,5-di-tert-butylphenyl)-1-methylpyridin-4(1H)-imine [MQItBu]H both gave isolable complexes. The species {[MQItBu]MgCl(THF)}2, {[MQItBu]MgMe}2, {[MQItBu]AlMe2}2 , {[MQItBu]ZnMe}2 , and {[MQIMe]MgCl(THF)}2 were prepared. As well, [MQI]H precursors were coordinated with Lewis acidic boron- and aluminium-derived Lewis acids. Charge delocalization onto pyridine was examined by crystallography and NMR spectroscopy.

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Synthesis of new Pro-PYE ligands as co-catalysts toward Pd-catalyzed Heck–Mizoroki cross coupling reactions

Cited by 10 publications

References 49 publications

Synthesis of Sulfonated Copolyimides by Thermal Imidization for Efficient Lead Ion Adsorption from Aqueous Media

Synthesis of Sulfonated Copolyimides by Thermal Imidization for Efficient Lead Ion Adsorption from Aqueous Media

Pyridylidene Amines and Amides: Donor-Flexible Ligands for Catalysis

Monoanionic Quasi-Imido Ligands Based on 1-Methyl-4-Iminopyridine and Complexes with the Main Group Elements Mg, Al and Zn.

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