Capturing CO2 using novel nonaqueous biphasic solvent TMEDA/MEA/DMSO: Absorption and phase splitting mechanism

Chemical Engineering Journal, Год журнала: 2024, Номер 484, С. 149293 - 149293

Опубликована: Фев. 3, 2024

Язык: Английский

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Visible‐Light‐Driven Multicomponent Radical Cascade Versatile Alkylation of Quinoxalinones Enabled by Electron Donor Acceptor Complex in Water

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(7), С. 1020 - 1026

Опубликована: Март 10, 2023

Abstract An operationally simple aqueous phase three‐component photochemical strategy for the alkylation of quinoxalin‐2(1 H )‐ones with diethyl α ‐bromomalonate and unactivated alkenes in absence both photoredox catalysts additive has been developed. This reaction is driven by activity electron donor‐acceptor (EDA) complexes formed ‐bromomalonate. Irradiation visible light triggered single‐electron transfer (SET) from to ‐bromomalonate, inducing formation corresponding alkyl radical subsequent tandem reaction. It provides an efficient way construct alkylated quinoxalinones small molecules. magnified image

Язык: Английский

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Photocatalytic Pyridine Synthesis with Enaminones and TMEDA under Metal-Free Conditions

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 11060 - 11066

Опубликована: Июль 24, 2024

Reported herein is a new photocatalytic annulation for the synthesis of 2,3,4,6-tetrasubstituted pyridines with enaminones and N,N,N′,N′-tetramethyl ethylenediamine (TMEDA). The reactions take place without requiring transition metal reagent provide products broad scope. methyl in TMEDA acts as carbon source pyridine ring construction, BrCF2CO2Et plays role terminal oxidant free radical quenching.

Язык: Английский

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Gem-Difluoroallylation of Aryl Sulfonium Salts

Organic Letters, Год журнала: 2022, Номер 24(48), С. 8753 - 8758

Опубликована: Ноя. 28, 2022

The unprecedented photochemical late-stage defluorinative gem-difluoroallylation of aryl sulfonium salts, which are formed site-selectively by direct C(sp2)─H functionalization, is herein disclosed. This method distinguished its mild reaction conditions, wide scope, and excellent site-selectivity. As showcase examples, a Flurbiprofen Pyriproxyfen derivatives could be late stage gem-difluoroallylated with high yields. Experimental computational investigations were conducted.

Язык: Английский

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Visible Light-Promoted Radical Relay Cyclization/C–C Bond Formation of N-Allylbromodifluoroacetamides with Quinoxalin-2(1H)-ones

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(23), С. 17173 - 17183

Опубликована: Ноя. 6, 2021

A visible light-promoted radical relay of N-allylbromodifluoroacetamide with quinoxalin-2(1H)-ones was developed in which 5-exo-trig cyclization and C–C bond formation were involved. This protocol performed under mild conditions to facilely offer a variety hybrid molecules bearing both quinoxalin-2(1H)-one 3,3-difluoro-γ-lactam motifs. These prepared novel skeletons would expand the accessible chemical space for structurally complex heterocycles potential biological activities.

Язык: Английский

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Demystifying the recent photochemical and electrochemical tricks on installing the magic methyl group: A comprehensive overview

Green Chemistry, Год журнала: 2024, Номер 26(14), С. 8161 - 8203

Опубликована: Янв. 1, 2024

The strategic installation of the “magic methyl” group has become highly desirable for drug discovery. This review summarized recent photochemical and electrochemical strategies in installing methyl group.

Язык: Английский

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Metal‐Free, Photoredox‐Catalyzed Synthesis of Quinazolin‐4(3H)‐ones and Benzo[4,5]imidazo[1,2‐c]quinazolines Using Trialkylamines as Alkyl Synthon

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(12)

Опубликована: Фев. 10, 2023

Abstract Highly functionalized quinazolin‐4(3 H )‐ones were synthesized from reactions of N ‐aryl‐2‐aminobenzamides with trialkylamines under photocatalytic conditions by using eosin Y (EY) as a catalyst. The reaction proceeds mild in aqueous acetonitrile and has broad substrate scope. Mechanistic studies disclosed the electron‐donor nature intermediate 2,3‐dihydroquinazolin‐4(1 )‐one ( 3’ ) cycle to afford 2,3‐disubstituted‐quinazolin‐4(3 3 ). This methodology been extended synthesize benzo [4,5] imidazole[1,2‐ c ] quinazolines aa on large scale. Furthermore, synthesis potent central nervous system depressant (CNS) drug molecules such methaqualone la mecloqualone pa was also achieved successfully.

Язык: Английский

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Photo‐Induced C−H Methylation Reactions

Chemistry - A European Journal, Год журнала: 2023, Номер 29(72)

Опубликована: Окт. 6, 2023

Direct C-H methylation is a highly valuable approach for introducing methyl groups into organic molecules, particularly in pharmaceutical chemistry. Among the various methodologies available, photo-induced stands out as an exceptional choice due to its mild reaction conditions, energy efficiency, and compatibility with functional groups. This article offers comprehensive review of photochemical strategies employed direct selective C(sp3 )-H, C(sp2 C(sp)-H bonds molecules. The discussed encompass transition-metal-based photocatalysis, organophotocatalysis, well other metal-free approaches, including electron donor-acceptor (EDA)-enabled transformations. Importantly, wide range easily accessible agents such tert-butyl peroxide, methanol, DMSO, ether, TsOMe, N-(acetoxy)phthalimide, acetic acid, halides, even methane can serve effective methylating reagents modifying diverse targets. These advancements are anticipated drive further progress fields synthesis, development, opening up exciting avenues creating novel molecules discovering new drug compounds.

Язык: Английский

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Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(51)

Опубликована: Сен. 5, 2024

Benzo[1,3,2]dithiazole-1,1,3-trioxides are bench-stable and easy-to-use reagents. In photoredox catalysis, they generate methyl perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, N-Ts acrylamide. As byproduct, salt is formed be regenerated the original methylating agent. Flow chemistry provides an option for reaction scale-up further underscoring synthetic usefulness these methylation Mechanistic investigations suggest single-electron transfer (SET) pathway induced by catalysis.

Язык: Английский

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Regioselective C-3-alkylation of quinoxalin-2(1H)-ones via C–N bond cleavage of amine derived Katritzky salts enabled by continuous-flow photoredox catalysis

RSC Advances, Год журнала: 2022, Номер 12(20), С. 12235 - 12241

Опубликована: Янв. 1, 2022

An efficient, transition metal-free visible-light-driven continuous-flow C-3-alkylation of quinoxalin-2(1 H )-ones has been demonstrated enabling excellent yields (72% to 91%) and shorter reaction time (0.81 min) as compared batch system (16 h).

Язык: Английский

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