Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
A visible-light-induced C-3 alkylation of quinoxalin-2(1 H )-ones with N , ′, ′-tetraalkylethylenediamine was achieved without an external photocatalyst.
Язык: Английский
Chemical Reviews, Год журнала: 2024, Номер unknown
Опубликована: Дек. 12, 2024
Since the seminal report by Adachi and co-workers in 2012, there has been a veritable explosion of interest design thermally activated delayed fluorescence (TADF) compounds, particularly as emitters for organic light-emitting diodes (OLEDs). With rapid advancements innovation materials design, efficiencies TADF OLEDs each primary color points well white devices now rival those state-of-the-art phosphorescent emitters. Beyond electroluminescent devices, compounds have also found increasing utility applications numerous related fields, from photocatalysis, to sensing, imaging beyond. Following our previous review 2017 (
Язык: Английский
Процитировано
20
ACS Catalysis, Год журнала: 2024, Номер 14(17), С. 13451 - 13496
Опубликована: Авг. 26, 2024
Alcohols are abundant with versatile structural variety and have ample use as pivotal functional groups in numerous organic processes. Because of their frequent occurrence enumerable natural products, bioactive molecules, medicinal components, alcohol functionalities provide a promising scope research to advance the operational diversity for improving clinical success. Recent years witnessed design modern C–C C–heteroatom bond-forming approaches easily accessible commercially available unactivated aliphatic alcohols native adaptive sp3 handles, hence offering groundbreaking transformative pathways functionalization complex molecular architectures. The judicial application appropriate activating generate alkyl radical from through C–O bond fragmentation employ it potential alkylating agent unfolds unique synthetic strategies, thereby replacing obvious requirement halides. This review elaborately discusses recent trends regarding using C(sp3)-centered various chemical transformations by exploiting different activation modes disrupter under photoredox catalysis. presentation is organized nature scaffolds, kind formation, progress achieved this domain since original discovery providing illustrative examples mechanistic details, focus on difficulties future prospects.
Язык: Английский
Процитировано
8
Organic Letters, Год журнала: 2024, Номер 26(2), С. 493 - 497
Опубликована: Янв. 8, 2024
An electrochemical hydrogen atom transfer (HAT) strategy for the direct amino-α-C–H heteroarylation of amides is described. The cheap TMSN3 acts as a reagent. A series heteroarenes including quinoxalin-2(1H)-ones, 4-methylquinoline, isoquinoline, 2-methylquinoxaline, benzothiazole, etc., and various readily available amides/lactams were suitable. reaction has characteristics wide range substrates, good regioselectivity, chemical oxidant-free conditions, etc.
Язык: Английский
Процитировано
8
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6334 - 6344
Опубликована: Апрель 15, 2024
A one-pot strategy for deoxygenative alkylation of alcohols with quinoxalin-2(1H)-ones was developed by using xanthate salts as alcohol-activating groups radical generation in the presence tricyclohexylphosphine under visible-light-promoted conditions. The remarkable features this reaction include a broad substrate scope, excellent functional group tolerance, mild conditions, and simple operation. Moreover, synthetic utility validated success two-step reactions, scale-up synthesis, chemoselective monodeoxygenation diols.
Язык: Английский
Процитировано
5
Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(6), С. 1157 - 1161
Опубликована: Янв. 1, 2024
Herein, a photoinduced direct C(sp 2 )–H alkylation of N -heteroaromatics by using commercially available tetrabutylammonium tribromide (TBATB) as HAT reagent is described.
Язык: Английский
Процитировано
4
Synlett, Год журнала: 2023, Номер 34(17), С. 2037 - 2041
Опубликована: Июнь 12, 2023
Abstract A visible-light-induced radical difluoroalkylation of quinoxalin-2(1H)-ones by hypervalent-iodine-based reagents was developed. To facilitate the final oxidative step, [bis(trifluoroacetoxy)iodo]benzene (PIFA) employed as an oxidant. Moreover, a one-pot protocol for this transformation realized generating reagent in situ. The readily accessible and mild reaction conditions make alternative practical strategy synthesis C(3)-difluoroalkylated quinoxalin-2(1H)-ones.
Язык: Английский
Процитировано
5
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11762 - 11766
Опубликована: Авг. 9, 2023
A metal-free addition of unactivated alkyl bromides to quinoxalin-2(1H)-ones is described. This method enables the construction valuable 3,3-disubstituted dihydroquinoxalin-2(1H)-ones bearing quaternary carbon centers under mild, visible-light photoredox catalysis. High functional group tolerance observed in both quinoxalinone and bromide partners. The ability scale up this was demonstrated photo-flow conditions enable gram-scale synthesis.
Язык: Английский
Процитировано
4
New Journal of Chemistry, Год журнала: 2023, Номер 47(47), С. 21596 - 21599
Опубликована: Янв. 1, 2023
Ionic liquid-catalysed oxygenation of quinoxalin-2(1 H )-one utilizing aerobic oxygen as a green oxidant under visible light conditions at room temperature is described.
Язык: Английский
Процитировано
4
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10760 - 10772
Опубликована: Июль 11, 2024
Lewis acid-mediated selective C3-isothiocyanation of quinoxalin-2(1
Язык: Английский
Процитировано
1
ACS Catalysis, Год журнала: 2024, Номер 14(19), С. 14574 - 14585
Опубликована: Сен. 16, 2024
A class of in-situ generated Lewis acid (LA) activated acridine complexes is reported, which act as potent photochemical catalysts for the oxidation a variety protected secondary amines. Acridine/LA exhibit tunable excited state reduction potentials ranging from +2.07 to 2.38 V vs. SCE. The ytterbium triflate complex 3,6-di-t-butyl-9-mesitylacridine catalyzes Giese-type reaction Boc-protected amines with challenging conjugate acceptors such acrylates, that are inaccessible analogous acridinium (t-Bu-Mes-Acr⊕) catalyzed reaction. mechanism this was investigated using suite physical organic probes including intramolecular 13C kinetic isotope effects (KIEs), variable time normalization analysis (VTNA) kinetics, determination redox potentials, and computational studies. In by t-Bu-Mes-Acr⊕, mechanistic studies consistent single-electron transfer (SET) ground-state reduced t-Bu-Mes-Acr• α-keto radical intermediate first irreversible step in catalytic cycle. Intriguingly, we find acridine/LA better ground reductants (-0.72 -0.74 vs SCE) relative (-0.59 predict increased substrate reactivity stems lower energy barrier key SET event.
Язык: Английский
Процитировано
1