Decatungstate-photocatalyzed direct acylation of N-heterocycles with aldehydes

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(12), P. 7331 - 7336

Published: Jan. 1, 2024

A novel photocatalytic acylation strategy was developed harnessing tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst to facilitate the direct coupling of aldehydes with N-heterocycles at ambient temperature.

Language: Английский

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Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions

Organic Letters, Journal Year: 2025, Volume and Issue: 27(10), P. 2526 - 2531

Published: March 5, 2025

Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification alkylation of quinoxalin-2(1H)-ones with aldehydes. A key feature our study is ability to perform both using different types The reaction system highly compatible a range aldehydes, yielding C3-esterified C3-alkylated products in moderate-to-good yields. applicability this approach further enhanced by its scalability through continuous-flow synthesis, late-stage modification significant molecules, product derivatization. Our mechanistic investigations reveal radical relay mechanism, triggered hydrogen atom transfer process.

Language: Английский

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Visible-Light-Promoted Deoxygenative Alkylation of Quinoxalin-2(1H)-ones with Activated Alcohols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6334 - 6344

Published: April 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.

Language: Английский

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Radical 1,3-Hydrosulfonylation of Vinyldiazo Compounds with Sulfinyl Sulfones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 4, 2025

Sulfinyl sulfones, as high-valence sulfurization reagents, are widely used to assemble sulfur sources on carbon skeletons, such one-, two-, and four-carbon synthons, access organosulfur compounds. However, their reaction with three-carbon synthons has remained a mystery until now. We report here radical 1,3-hydrosulfonylation of vinyldiazo compounds sulfinyl sulfones. This not only represents the first example sulfones but also opens up application in monofunctionalization.

Language: Английский

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Synthesis of Nonclassical Heteroaryl C-Glycosides via Decarboxylative C–H Glycosylation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10112 - 10126

Published: July 3, 2024

A photoredox-promoted decarboxylative C-H glycosylation for the synthesis of nonclassical heteroaryl C-glycosides is reported. This methodology characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. Moreover, operational procedure simple, gram-scale highlights practical applicability this protocol.

Language: Английский

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Decatungstate-photocatalyzed radical addition of C(sp³)–H to azauracils

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5791 - 5797

Published: Jan. 1, 2024

This study presents a gentle and effective decatungstate ([W 10 O 32 ] 4− )-photocatalyzed method for the hydroalkylation of azauracils using wide range primary, secondary, tertiary unreactive C–H bonds alkanes as alkylating reagents.

Language: Английский

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Base-mediated denitrative C3-alkylation of quinoxaline derivatives

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A novel base-mediated C3-alkylation of quinoxalin-2(1 H )-one and its N -protected derivatives using inexpensive nitroalkanes has been developed. This method is scalable tolerates diverse functional groups supports bioactive compound synthesis.

Language: Английский

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Acid‐Promoted Self‐Photocatalyzed Regioselective Oxidation: A Novel Strategy for Accessing Quinoxaline‐2,3‐diones

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(68)

Published: Aug. 29, 2024

Abstract Disclosed here is an efficient approach for the preparation of quinoxaline‐2,3‐diones using air (O 2 ) as a green oxidant via acid‐promoted self‐photocatalyzed regioselective oxidation quinoxalin‐2(1 H )‐ones at C‐3 position. This protocol presents novel synthetic route quinoxaline‐2,3‐dione derivatives, featuring mild reaction conditions, simple operation, and wide range substrates, without need external photocatalysts, metal reagents, strong oxidants.

Language: Английский

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