Acridine yellow G as a photo-induced electron transfer catalyzed radical [4 + 2] aza-Diels-Alder annulation of imines

For the preparation of polyfunctionalized piperidine scaffolds, a radical tandem five-condensation domino Knoevenagel-intramolecular [4 + 2] aza-Diels-Alder imin-based reaction was used. Based on acridine yellow G (AYG) as a photo-induced electron transfer (PET) photocatalyst, employing visible light as a renewable source of energy. AYG that is photochemically catalyzed has good yields, as well as outstanding atom economy, and ease of operation. As a result, a diverse set of chemical and environmental parameters can be measured across time. The turnover number (TON) and turnover frequency (TOF) of polyfunctionalized piperidine scaffolds have been computed. Also, gram-scale cyclization can occur, suggesting that the process might find application in industry.

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Publication Details

Journal
Results in Chemistry
Published
2024-10-01
DOI
https://doi.org/10.1016/j.rechem.2024.101843
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Acridine yellow G as a photo-induced electron transfer catalyzed radical [4 + 2] aza-Diels-Alder annulation of imines

Farzaneh Mohamadpour
Results in Chemistry
Radical Photochemical Reactions
article

Acridine yellow G as a photo-induced electron transfer catalyzed radical [4 + 2] aza-Diels-Alder annulation of imines

Farzaneh Mohamadpour
article en

Abstract

For the preparation of polyfunctionalized piperidine scaffolds, a radical tandem five-condensation domino Knoevenagel-intramolecular [4 + 2] aza-Diels-Alder imin-based reaction was used. Based on acridine yellow G (AYG) as a photo-induced electron transfer (PET) photocatalyst, employing visible light as a renewable source of energy. AYG that is photochemically catalyzed has good yields, as well as outstanding atom economy, and ease of operation. As a result, a diverse set of chemical and environmental parameters can be measured across time. The turnover number (TON) and turnover frequency (TOF) of polyfunctionalized piperidine scaffolds have been computed. Also, gram-scale cyclization can occur, suggesting that the process might find application in industry.

Results in ChemistryVol. 11
Sadra Institute Of Higher Education (IR)
Openalex Percentile: Top 87%
Radical Photochemical Reactions
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