Light-fuelled nitro-reduction via cascaded electron donor–acceptor complexes in aqueous media

The photochemistry of EDA complexes is initiated from a ground-state associate with a biomolecule capable of intermolecular electron transfer by channelling chemical synthesis via a specific radical-based mechanistic pathway. Herein, we activate the innovative cascade mode of EDA complex photoexcita...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2024-09, Vol.26 (18), p.9682-9689
Main Authors: Zhuang, Xiaohui, Song, Haijing, Wang, Jiayin, Zhang, Zhaokang, Wang, Jiayang, Sun, Bin, Su, Weike, Jin, Can
Format: Article
Language:English
Subjects:
Amines
Aqueous solutions
Biomolecules
Charge transfer
Chemical synthesis
Electron transfer
Glycine
NMR
Nuclear magnetic resonance
Organic compounds
Photochemistry
Photoexcitation
Titration
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Summary:The photochemistry of EDA complexes is initiated from a ground-state associate with a biomolecule capable of intermolecular electron transfer by channelling chemical synthesis via a specific radical-based mechanistic pathway. Herein, we activate the innovative cascade mode of EDA complex photoexcitation for nitro-reduction in aqueous media using charge transfer interactions between a sole donor and multiple acceptors (ArNO 2 , ArNO, and ArNHOH·glycine adduct). A triplet-state quenching experiment, UV-vis analysis, NMR titration, and preliminary kinetic investigation verified the rationality and feasibility of the mechanism. With successful applications of this cascaded system in arylamine compounds and commercially available drug synthesis (61 examples), these achievements highlight the attractiveness, usefulness, and effectiveness of this protocol.
ISSN:1463-9262
1463-9270
DOI:10.1039/D4GC02602K