Singlet oxygen mediated one pot synthesis of N-pyridinylamides via oxidative amidation of aryl alkyl ketones

Sofi, Firdoos Ahmad; Sharma, Rohit; Kavyasree, S.N.; Salim, Sumi Aisha; Wanjari, Pravin J.; Bharatam, Prasad V.

doi:10.1016/j.tet.2019.130536

Cited by 6 publications

(6 citation statements)

References 41 publications

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“…Ru(II) tris-bipiridine [Ru(bpy) 3 2+ ] is a celebrated example, which features a strong metal-to-ligand charge transfer (MLCT) absorption band at 452 nm and enhanced stability . In particular, Ru(bpy) 3 2+ has been reported as an active photocatalyst capable of generating singlet oxygen ( 1 O 2 ), which is a powerful metastable oxidant with extremely rich reactivity. , Singlet oxygen is well known for its reactions with alkenes, but it can also oxidize amines, sulfides, and phosphines . It is viewed as a key method in the total synthesis toolbox, as examplified with the semisynthesis of artemisin, a major malaria drug .…”

Section: Introductionmentioning

confidence: 99%

Photocatalysis Meets Magnetism: Designing Magnetically Recoverable Supports for Visible-Light Photocatalysis

Terra

Desgranges

Monnereau

et al. 2020

ACS Appl. Mater. Interfaces

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While magnetic supports have been widely used to immobilize homogeneous catalysts in organic chemistry, this strategy has so far found very little application in photocatalysis. Indeed, magnetic supports are dark colored, and thus compete for photon absorption with photocatalysts themselves. We have developed a series of core–shell Fe(0)-silica nanoparticles as supports for immobilizing the photosensitizer Ru(bpy)3 2+, featuring various silica shell thicknesses16–34 nm SiO2on 9 nm Fe cores. The supports and the resulting photocatalytic systems were studied for their magnetic, optical, and catalytic properties in the context of the photooxidation of citronellol, and we found that thicker silica shells lead to higher catalytic activity. We correlated this effect as well as Ru(bpy)3 2+ fluorescence and singlet oxygen generation to the absorption properties of the supports. We were able to reuse our optimal system three times with minimal loss of activity and achieved turnover numbers largely surpassing the performance of homogeneous Ru(bpy)3 2+. This work highlights the role of material design in the conception of new supports for applications in heterogeneous photocatalysis.

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Section: Introductionmentioning

confidence: 99%

Photocatalysis Meets Magnetism: Designing Magnetically Recoverable Supports for Visible-Light Photocatalysis

Terra

Desgranges

Monnereau

et al. 2020

ACS Appl. Mater. Interfaces

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“…However, if the reactant concentration was too high, it had a negative effect on the reaction performance (entries 18 and 19). In fact, a 1:1.2 ratio of reagents was previously studied by Sofi et al , 50 who obtained good yields. Moreover, we investigated the substrate scope utilizing Ni‐BDC as the catalyst (Table 2).…”

Section: Resultsmentioning

confidence: 98%

“…However, when the reaction was carried out over 90 °C, the reaction performance decreased (entries 5 and 6). This result could be explained by the intermediate compound formed during the reaction process 50 that may be unstable at high temperatures. Previous research has also shown that N ‐(pyridin‐2‐yl)benzamides can be synthesized at low temperatures 4,51 …”

Section: Resultsmentioning

confidence: 99%

“…While many homogeneous catalyst systems show high activity and selectivity in the C N cross-coupling reaction to form N-(pyridin-2-yl)benzamide, there are no reports in previous literature on the recovery and reuse ability of these catalyst systems. 4,50,61 In contrast, solid catalysts have the advantage of being easily separated from the reaction mixture, recovered, and reused, compared to homogeneous catalysts. Therefore, we investigated the recovery and reuse of the Ni-BDC catalyst in the C N cross-coupling reaction between 2-aminopyridine and aryl aldehydes.…”

Section: Investigation Of Catalytic Activity For Synthetic Reaction O...mentioning

confidence: 99%

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Ni‐based metal organic frameworks: an efficient catalyst for the amidation reaction to obtain N‐(pyridin‐2‐yl)arylamides

Nguyen

Nong

2023

J of Chemical Tech & Biotech

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BackgroundAmides are the essential building blocks of natural products and bioactive molecules. One of the most common structures discovered in medicinal and bioactive compounds is amide derivatives. The synthesis of N‐(pyridin‐2‐yl)arylamide compounds has recently been assessed using various methods. In particular, there is growing interest in employing heterogeneous catalysts to catalyze organic synthesis reactions. Metal organic frameworks based on nickel centers were synthesized using the solvothermal method. The morphology, size, and catalytic activity of Ni‐based catalysts strongly depend on the substitute solvent composition in the reaction system. The structural features of the Ni‐based materials were verified using modern analytical techniques.ResultsNi‐based materials were used to catalyze the synthesis of physiologically important N‐(pyridin‐2‐yl)arylamides through an amidation reaction between 2‐aminopyridine and benzaldehyde. Temperature, reaction time, catalyst amount, reactant ratio, and solvent type were investigated as factors that influenced the catalytic activity. The optimal reaction conditions were 10 mol% Ni‐based catalysts, tetrahydrofuran as the reaction solvent, and a reaction temperature of 90 °C for 24 h. N‐(pyridin‐2‐yl)arylamide was obtained in approximately 85% yield. The catalyst could be recovered and reused without significant loss of catalytic activity (79%) after six runs.ConclusionThis study illustrated that the Ni‐based catalyst performed well in the reaction between 2‐aminopyridine and benzaldehyde formation N‐(pyridin‐2‐yl)arylamide compound with an 85% yield. The solid catalyst was recovered and reused up to six times without any significant change in catalytic activity. © 2023 Society of Chemical Industry (SCI).

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“…Based on the information from these experiments and related literature reports, [66,67] a reasonable mechanism for the forming of the N-Pyridinyl benzamide has been proposed. As outlined in Scheme 2, thermolysis of di-tert-butyl peroxide (DTBP) creates t-BuO radical.…”

Section: Samplesmentioning

confidence: 89%

Efficient Synthesis of N‐Pyridinylamides Using a Bimetallic Co/Fe‐Metal‐Organic Framework Heterogeneous Catalyst

Nguyen,

Nong,

Nguyen

et al. 2023

ChemistrySelect

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The synthesis of N‐pyridinylamides has been realized by particularly efficient technologies via bimetallic organic (Co/Fe‐MOF) catalyzed oxidative amidation between 2‐aminopyridine and benzaldehyde. The C−N bond was formed with the presence of a catalyst (Co/Fe‐MOF) as a Lewis acid and the oxidant as DTBP. The oxidative amidation reaction was conducted in 1,4‐dioxane at 120 °C with a wide range of substrates producing the corresponding amide products in good to 94 % yields. Experimental results illustrated that This accessibly offers a significant improvement over the earlier successful attempts in forming N‐pyridinyl amides. The Co/Fe‐MOF material was synthesized by solvothermal methods with the salt mixture of Fe(NO3)3.9H2O and Co(NO3)2.6H2O. The material was determined by modern analytic methods like X‐ray diffraction (XRD), Fourier‐transform Infrared spectroscopy (FT‐IR), Scanning Electron Microscope (SEM), and N2 adsorption/desorption isotherms.

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Singlet oxygen mediated one pot synthesis of N-pyridinylamides via oxidative amidation of aryl alkyl ketones

Cited by 6 publications

References 41 publications

Photocatalysis Meets Magnetism: Designing Magnetically Recoverable Supports for Visible-Light Photocatalysis

Photocatalysis Meets Magnetism: Designing Magnetically Recoverable Supports for Visible-Light Photocatalysis

Ni‐based metal organic frameworks: an efficient catalyst for the amidation reaction to obtain N‐(pyridin‐2‐yl)arylamides

Efficient Synthesis of N‐Pyridinylamides Using a Bimetallic Co/Fe‐Metal‐Organic Framework Heterogeneous Catalyst

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