Visible-light-driven radical Friedländer hetero-annulation of 2-aminoaryl ketone and α-methylene carbonyl compound via organic dye fluorescein through a single-electron transfer (SET) pathway

Mohamadpour, Farzaneh

doi:10.1186/s13065-022-00910-1

Cited by 3 publications

(1 citation statement)

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“…Furthermore, it is difficult to separate a homogeneous catalyst from the reaction mixture. The goal of our study was to look at photocatalysts [36][37][38][39] in green environments in order to synthesize heterocyclic compounds, which have been attempted before. This study also shows how to employ a metal-free cationic dye photo-redox catalyst that is inexpensive and widely available.…”

Section: Introductionmentioning

confidence: 99%

Methylene blue as a photo‐redox catalyst employed for the synthesis of pyrano[2,3‐d]pyrimidine scaffolds via a single‐electron transfer/energy transfer pathway

Mohamadpour

2023

Journal of Heterocyclic Chem

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The radical tandem Knoevenagel‐Michael cyclocondensation reaction of barbituric acid/1,3‐dimethylbarbituric acid, malononitrile, and aryl aldehydes was used to establish a green tandem method for the metal‐free synthesis of pyrano[2,3‐d]pyrimidine scaffolds. At ambient temperature, photo‐excited state functions made from methylene blue (MB+) were used as single‐electron transfer and energy transfer catalysts in an aqueous solvent, utilizing visible light as a sustainable energy source. The purpose of this project is to enhance the use of a non‐metal cationic dye that is both affordable and widely available. Methylene blue is photochemically catalyzed with the least amount of catalyst feasible, yielding excellent yields, energy efficiency, and environmental friendliness, as well as excellent atom economy, time‐saving features, and ease of operation. As a result, a wide range of environmental and long‐term chemical properties can be obtained. The pyrano[2,3‐d]pyrimidine scaffolds' turnover number and turnover frequency have been calculated. Surprisingly, gram‐scale cyclization is conceivable, indicating that the technology could be used in industry.

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Section: Introductionmentioning

confidence: 99%

Methylene blue as a photo‐redox catalyst employed for the synthesis of pyrano[2,3‐d]pyrimidine scaffolds via a single‐electron transfer/energy transfer pathway

Mohamadpour

2023

Journal of Heterocyclic Chem

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Polyfluorinated alcohol as a reusable media promoted catalyst-free green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives

Mohamadpour

2024

Results in Chemistry

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Halogenated dicyanobenzene-based photosensitizer (3DPAFIPN) as a thermally activated delayed fluorescence (TADF) used in gram-scale photosynthesis 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives via a consecutive visible-light-induced electron-transfer pathway

Mohamadpour,

Amani

2024

Front. Chem.

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Background: Organic dyes often have shorter lifetimes in the excited state, which is a major obstacle to the development of effective photoredox methods. The scientific community has shown a great deal of interest in a certain class of organic chromophores because of their unique characteristics and effectiveness. One characteristic of the molecules under research is thermally activated delayed fluorescence (TADF), which is only observed in molecules with a tiny energy gap (often less than 0.2 eV) between their lowest two excited states, i.e., singlet excited state (S1) and triplet excited state (T1). The extended singlet excited states arising from TADF and the simplicity with which their redox potentials may be altered make the isophthalonitrile family of chromophores an attractive option for organic photocatalyst applications.Methods: The Biginelli reaction between β-ketoesters, arylaldehydes, and urea/thiourea has been used to build a sustainable technique for the production of 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives. In the present study, the development of a green radical synthesis approach for this class of compounds is addressed in depth. As a photocatalyst, a new halogenated dicyanobenzene-based photosensitizer was employed in this study. As a renewable energy source activated by a blue LED, it was dissolved in ethanol, at room temperature in air atmosphere. The primary objective of this research is to employ a novel donor-acceptor (D-A) based on halogenated cyanoarene that is affordable, easily available, and innovative.Findings: The 3DPAFIPN [2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile] photocatalyst, a thermally activated delayed fluorescence (TADF), induces single-electron transfer (SET) in response to visible light, offering a straightforward, eco-friendly, and highly efficient process. Additionally, we determined the 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives turnover frequency (TOF) and turnover number (TON). It has also been demonstrated that gram-scale cyclization is a workable method for industrial purposes.

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Visible-light-driven radical Friedländer hetero-annulation of 2-aminoaryl ketone and α-methylene carbonyl compound via organic dye fluorescein through a single-electron transfer (SET) pathway

Cited by 3 publications

References 56 publications

Methylene blue as a photo‐redox catalyst employed for the synthesis of pyrano[2,3‐d]pyrimidine scaffolds via a single‐electron transfer/energy transfer pathway

Methylene blue as a photo‐redox catalyst employed for the synthesis of pyrano[2,3‐d]pyrimidine scaffolds via a single‐electron transfer/energy transfer pathway

Polyfluorinated alcohol as a reusable media promoted catalyst-free green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives

Halogenated dicyanobenzene-based photosensitizer (3DPAFIPN) as a thermally activated delayed fluorescence (TADF) used in gram-scale photosynthesis 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives via a consecutive visible-light-induced electron-transfer pathway

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