Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7531 - 7540

Опубликована: Май 18, 2024

An organocatalyzed photoelectrochemical method for the generation of acyl and phosphoryl radicals from formamides, aldehydes, phosphine oxides has been developed. This protocol utilizes 9,10-phenanthrenequinone (PQ) as both a molecular catalyst hydrogen atom-transfer (HAT) reagent, eliminating requirement external metal-based reagents, HAT oxidants. The generated can be applied to range radical-mediated transformation reactions, including C–H carbamoylation heteroarenes, intermolecular tandem radical cyclization CF3-substituted N-arylacrylamides, well intramolecular reactions. use in these transformations offers an efficient sustainable approach accessing structurally diverse carbonyl compounds.

Язык: Английский

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Iron-catalyzed methylation of quinoxalin-2(1H)-ones with dimethyl sulfoxide under visible light irradiation

Molecular Catalysis, Год журнала: 2024, Номер 558, С. 113999 - 113999

Опубликована: Март 11, 2024

Язык: Английский

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Modulating β‐Keto‐enamine‐Based Covalent Organic Frameworks for Photocatalytic Atom‐Transfer Radical Addition Reaction

Chemistry - A European Journal, Год журнала: 2024, Номер 30(24)

Опубликована: Фев. 26, 2024

The atom-transfer radical addition (ATRA) reaction simultaneously forges carbon-carbon and carbon-halogen bonds. However, frequently-used photosensitizers such as precious transition metal complexes, or organic dyes have limitations in terms of their potential toxicity recyclability. Three β-ketoenamine-linked covalent frameworks (COFs) from 1,3,5-triformylphloroglucinol 1,4-phenylenediamines with variable transient photocurrent photocatalytic activity been prepared. A COF bearing electron-deficient Cl atoms displayed the highest toward ATRA polyhalogenated alkanes to give halogenated olefins under visible light at room temperature. This heterogeneous photocatalyst exhibited good functional group tolerance could be recycled without significant loss activity.

Язык: Английский

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BPO-promoted [4 + 2] cyclization of enaminones and o-phenylenediamines to 2-acyl quinoxalines via a cascade transamination and C–H amination

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(20), С. 4067 - 4071

Опубликована: Янв. 1, 2024

Rapid assembly of quinoxalines in a single step from readily available precursors has been recognized as an ideal platform terms efficiency and operation. Herein, we report BPO-promoted metal-free approach to 2-acyl enaminones

Язык: Английский

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NHPI-Mediated FeTiO₃-Photocatalyzed Semiheterogeneous Decarboxylative Acylarylation of Acrylamides with α-Oxocarboxylic Acids under Nitrogen

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12693 - 12700

Опубликована: Авг. 26, 2024

FeTiO3 has emerged as an interesting semiconductor photocatalyst in organic synthesis. We herein describe a visible-light-induced semiheterogeneous strategy for the synthesis of 3-(2-oxoethyl)indolin-2-ones with moderate to good yields and functional group compatibility using recyclable NHPI redox catalyst.

Язык: Английский

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Synthesis of Difluorocyclopropanes via a Photoinduced [1＋2] Cycloaddition of Diazo Esters with gem-Difluoroalkenes

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(1), С. 256 - 256

Опубликована: Янв. 1, 2025

Язык: Английский

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Controlled Defluorinative Carboxylation Cascade of Sterically Hindered CF₃-Alkenes with Formate Salt via Photocatalysis

Organic Letters, Год журнала: 2025, Номер 27(10), С. 2492 - 2497

Опубликована: Март 5, 2025

A controlled cleavage of double C-F bonds in sterically hindered tetrasubstituted CF3-alkenes using formate salt has been achieved through a photoinduced electron transfer approach. Diverse γ-branched multifunctionalized gem-difluoroalkenes and α-fluoroacrylic acids are obtained sequentially via hydrodefluorination bond carboxylation with good-to-high yields. Precisely controlling the quantity reaction time is crucial for obtaining divergent defluorinative products. Formate serves as C1 source, hydrogen donor, reducing agent.

Язык: Английский

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Visible-light-induced C–S bond formation of pyrazolin-5-ones with thioureas to pyrazol-4-yl carbamimidothioates

Molecular Catalysis, Год журнала: 2025, Номер 580, С. 115086 - 115086

Опубликована: Апрель 8, 2025

Язык: Английский

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Photo-induced decarboxylative radical cascade cyclization of unactivated alkenes: access to CF- and CF₂-substituted ring-fused imidazoles

RSC Advances, Год журнала: 2025, Номер 15(16), С. 12739 - 12745

Опубликована: Янв. 1, 2025

A mild and effective visible-light-induced decarboxylative radical cascade reaction of olefin-containing imidazoles α-fluorinated carboxylic acids, has been developed to afford monofluoromethylated or aryldifluoromethylated polycyclic imidazoles.

Язык: Английский

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Access to quaternary-carbon-containing β-alkyl amides via persulfate-promoted domino alkylation/smiles rearrangement of alkenes

RSC Advances, Год журнала: 2025, Номер 15(20), С. 16183 - 16186

Опубликована: Янв. 1, 2025

An efficient radical alkylative annulation/arylation of N -(arylsulfonyl)acrylamide with 4-alkyl-1,4-dihydropyridines (DHP) was developed for synthesizing all-carbon quaternary-centered β-alkyl amides.

Язык: Английский

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