This paper describes an efficient, sustainable, one-step procedure for synthesizing substituted phenazines and phenoxazinones from commercially available -substituted aromatic amines with very good yield (≥80%) in water. The procedure uses eosin Y (EY) as a photoredox catalyst at room temperature (RT). The highly reactive -quinone-diimine or -quinone-imine intermediate was characterized by the HR-MS technique.
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http://dx.doi.org/10.1021/acs.orglett.1c00725 | DOI Listing |
Org Biomol Chem
December 2024
Department of Chemistry, Rishi Bankim Chandra College for Women, Naihati, 24-Parganas (N), Pin-743165, India.
The application of visible light as an energy source provides a new avenue in organic transformation due to its mildness, efficiency and selectivity. In fact, recent years have witnessed remarkable advances in photoinduced decarboxylative coupling reactions involving carboxylic acids and their derivatives. Under appropriate photoredox conditions they undergo single electron transfer (SET), resulting in reactive radicals which can assemble with suitable reaction partners.
View Article and Find Full Text PDFMolecules
November 2024
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russia.
Photoredox-catalyzed phosphonylation of bromo-substituted 1,10-phenanthrolines under visible light irradiation was studied. The reaction was shown to proceed under mild conditions with Eosin Y as a photocatalyst in DMSO under blue light irradiation. It is transition-metal-free and affords the target phosphonate-substituted 1,10-phenanthrolines in moderate yields (26-51%) in 22 to 40 h.
View Article and Find Full Text PDFChem Commun (Camb)
October 2024
School of Polymer Science and Polymer Engineering, University of Akron, Akron, OH, 44325, USA.
Back electron transfer (BET) in eosin Y (EY) photoredox catalysis was visualized the fluorescence of single EYs. BET between the radical ion pair formed in photoinduced electron transfer (PET) induced photoblinking of single EYs under constant photoexcitation. Commonly used quenchers, alkyl bromides and a tertiary amine, were studied.
View Article and Find Full Text PDFJ Org Chem
October 2024
School of Applied Material Sciences, Centre for Applied Chemistry, Central University of Gujarat, Sector-30, Gandhinagar 382030, India.
A visible light-driven photoredox-catalyzed direct C(sp)-H functionalization of N-H free indoles with quinoxalinones generated in situ from 2,2-dihydroxy-1-indene-1,3(2)-dione and phenylene-1,2-diamines has been reported with the aid of Na-Eosin Y as the photocatalyst and the Hünig base as the sacrificial electron and proton donor. The reaction provides easy access to a variety of quaternary-centered C-3 selective indole-substituted tertiary alcohols in good yields. Mechanistic studies demonstrated the realization of photoredox-catalyzed in situ quinoxalinone formation and their proton-coupled single electron reduction to the corresponding ketyl radicals followed by cross-coupling with indoles.
View Article and Find Full Text PDFACS Appl Mater Interfaces
October 2024
Photocatalytic reduction reactions occasionally utilize sacrificial agents to scavenge photogenerated holes, thus enhancing the kinetics and efficiency of electron harvesting. However, exploring alternative hole-mediated oxidation reactions and their potential impact on photoredox processes is limited. This study investigates the products resulting from the oxidation of ethanol, a commonly used hole scavenger, and the underlying mechanisms involved.
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