Visible Light-Induced C–H Alkylation of Azauracils with N-Hydroxyphthalimide Esters via Catalytic EDA Complex

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 13, 2025

Herein, we report sodium iodide (NaI)-catalyzed decarboxylative C–H alkylation of azauracils with N-hydroxyphthalimide (NHPI) esters facilitated by visible light activation catalytic electron donor–acceptor (EDA) complexes. Control experiments and density functional theory calculations suggest that the coupling reaction proceeds via a transiently assembled EDA complex between NHPI ester NaI in N,N-dimethylacetamide solvent. This synthetic method efficiently applies to primary, secondary, tertiary under mild, photocatalyst-free, redox-neutral conditions, achieving high yields desired alkylated azauracils.

Язык: Английский

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Electron-Donor-Mediated Divergent Transformation of Br–R_F via EDA Complex for the Synthesis of Fluorine-Containing Oxindoles and Amides

Organic Letters, Год журнала: 2024, Номер 26(46), С. 9990 - 9995

Опубликована: Ноя. 11, 2024

We have developed an unprecedented electron-donor-controlled divergent reaction between

Язык: Английский

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Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This review summarizes recent progress in EDA complex-promoted C–S bond formation using various sulfur-containing substrates under mild conditions via visible light irradiation.

Язык: Английский

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Photoinduced Metal‐/Additive‐Free Difluoromethylation of N‐Heteroaromatics^†

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 16, 2025

Comprehensive Summary Herein, we report a photo‐induced, metal‐/additive‐free protocol for the difluoromethylation of N ‐heteroaromatics with [bis(difluoroacetoxy)iodo]benzene as reagent. The affords difluoromethylated in moderate to good yield (up 91%). transformation is compatible wide range substrates and has tolerance towards various functional groups. Moreover, synthetic value this method further demonstrated by applications gram‐scale synthesis late‐stage functionalization biologically important molecules.

Язык: Английский

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Organophotocatalytic Three‐Component Assembly of C4‐Cyanoalkylated Phthalazin‐1(2H)‐Ones

Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown

Опубликована: Фев. 14, 2025

Abstract The present work documents construction of C4‐cyanoalkylated phthalazinones under visible light‐mediated conditions. three‐component reaction involving aryl hydrazines, 2‐formylbenzoic acids and cyclobutanone oxime esters with organic dye Eosin Y as photocatalyst, features initial formation subsequent cyanoalkylation phthalazin‐1(2H)‐one in one pot. is notable for mild conditions, operational simplicity, wide substrate scope good yields the products. phthalazinone products were further converted into other valuable derivatives.

Язык: Английский

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Minisci C–H Alkylation of Heterocycles with Unactivated Alkyl Iodides Enabled by Visible Light Photocatalysis

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 27, 2025

In this work, we developed a general catalytic strategy that allows Minisci C-H alkylation of variety heterocycles using unactivated alkyl halide as an radical source under visible light photocatalysis. Mild reaction conditions, employing 4CzIPN organophotocatalyst and aerial oxygen green terminal oxidant, broad scope, good functional group tolerance, late-stage bioactive pharmaceutically relevant molecules are advantages the protocol. Preliminary mechanistic studies indicate involvement α-amino further our conditions.

Язык: Английский

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The organophotocatalytic trifluoromethylation of 6-azauracils

RSC Advances, Год журнала: 2025, Номер 15(15), С. 11370 - 11376

Опубликована: Янв. 1, 2025

Herein, we have developed an organophotocatalytic trifluoromethylation of 6-azauracils using inexpensive Langlois reagent to prepare a variety trifluoromethylated azauracil derivatives under ambient air condition.

Язык: Английский

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Silver-catalyzed direct decarboxylative C H functionalization of azauracils with aliphatic carboxylic acids

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155619 - 155619

Опубликована: Апрель 1, 2025

Язык: Английский

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Visible-Light-Induced C–H Alkylation of 1,2,4-Triazine-3,5(2H,4H)-diones via Infrequent 1,2-Hydrogen-Atom Transfer

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 19, 2025

1,2,4-Triazine-3,5(2H,4H)-diones are widely present in various drug molecules and bioactive molecules. A visible-light-driven C-H alkylation of 1,2,4-triazine-3,5(2H,4H)-diones via 1,2-hydrogen-atom transfer (1,2-HAT) amide radicals is first reported, providing an environmentally friendly sustainable pathway to enrich the structural functional diversity 1,2,4-triazine-3,5(2H,4H)-diones. This novel protocol characterized by mild metal-free reaction conditions, operationally simple method, good group tolerance. To our delight, other heterocycles, such as isoquinoline coumarin, also undergo reactions construct C(sp2)-C(sp3) bonds infrequent 1,2-HAT under current conditions.

Язык: Английский

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Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 20, 2025

A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor 6-azauracil nucleobase. The method exhibits high α-selectivity excellent functional group tolerance. Spectroscopic evidence shows that coupling reaction happens via initial reductive quenching Ir(III) catalyst under light. Density theory calculation reveals reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making process a valuable platform C-nucleosides.

Язык: Английский

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