Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(11), P. 2830 - 2848

Published: Jan. 1, 2023

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds and their mechanistic insights synthetic applications have been summarized.

Language: Английский

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Rh(III)‐Catalyzed Cascade Cyclization of 2‐Aryl‐3H‐indoles and CF₃‐Imidoyl Sulfoxonium Ylides Toward Trifluoroacetimidoyl‐Substituted 11H‐Isoindolo[2,1‐a]indoles

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3855 - 3860

Published: Oct. 18, 2023

Abstract A rhodium(III)‐catalyzed C−H activation/[4+1] annulation of 2‐aryl‐3 H ‐indoles and CF 3 ‐substituted imidoyl sulfoxonium ylides (TFISYs) has been achieved, producing a wide variety trifluoroacetimidoyl‐substituted 11 ‐isoindolo[2,1‐a]indoles in 51–86% yields. The cascade reaction involves imidoylmethylation, tautomerization AgOAc‐mediated C−N bond formation sequence. could be scaled up to 2 mmol scale.

Language: Английский

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Iodine-Mediated C2,3–H Aminoheteroarylation of Indoles

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15106 - 15117

Published: Oct. 21, 2023

A metal-free one-pot oxidative cross-dehydrogenation coupling reaction for the formation of C-N/C-C bonds at C2,3-positions indoles with azoles and quinoxalinones has been developed. The proposed method several notable features, including catalysis, use N-H free as substrates, ease operation, mild conditions, compatibility a wide range substrates.

Language: Английский

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Radical strategies for chemodivergent cyclization reactions

Trends in Chemistry, Journal Year: 2023, Volume and Issue: 5(12), P. 906 - 919

Published: Nov. 7, 2023

Language: Английский

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Orthogonal Synthesis of Cationic Azatriphenylene Derivatives for Aggregation-Induced Emission (AIE) and Aggregation-Caused Quenching (ACQ) Property Switching

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

Published: May 4, 2025

Herein, we report a divergent synthesis of cationic azatriphenylene derivatives using orthogonal control thermal and electro-oxidative pyridination, which transforms the single precursor into controlled products with perfect selectivity. Simultaneously, two switchable reactions afford corresponding pyridinium salts different optical properties such as aggregation-induced emission (AIE) aggregation-caused quenching (ACQ) effects.

Language: Английский

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A Lewis Acid-Catalyzed Cascade Synthesis of Fused N-Heterocycles from 2-Alkynylanilines and 2-Formylbenzonitriles: Unveiling Iminoisoindoloindolone and Its Derivatives

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12128 - 12142

Published: Aug. 22, 2024

We herein reveal a streamlined synthesis of structurally fused 6-iminoisoindoloindolones via meticulously orchestrated cascade reaction. This process seamlessly intertwines 2-alkynylaniline and 2-formylbenzonitrile under the catalytic influence TMSOTf, giving rise to these compounds in remarkable yields that stand as testament efficiency our approach. Moreover, versatility this synthetic strategy extends far beyond mere synthesis, offering gateway creation both isoindoloindolone unprecedented diphenylbenzopyrrolizinoisoquinolinone derivatives, thereby opening new horizons realm chemical innovation. Furthermore, strategic elegance methodology is underscored by its potential for scale-up production applicability across diverse contexts.

Language: Английский

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Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(4), P. 108902 - 108902

Published: Aug. 9, 2023

Language: Английский

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Mn(OAc)₃-Promoted Sulfonation–ipso-Cyclization Cascade via the SO₃^– Radical: The Synthesis of Spirocyclic Sulfonates

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 14140 - 14155

Published: Sept. 18, 2023

A radical sulfonation–ipso-cyclization cascade promoted by Mn(OAc)3·2H2O using functionalized alkynes or alkenes and potassium metabisulfite (K2S2O5) is reported. total of 30 spirocyclic sulfonates were synthesized under mild conditions. We also demonstrate a modular synthesis approach in multiple steps for the preparation various azaspiro[4,5]-trienone-based sulfonamides sulfonate esters.

Language: Английский

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Chemodivergent Photocatalyzed Heterocyclization of Hydrazones and Isothiocyanates for the Selectivity Synthesis of 2-Amino-1,3,4-thiadiazoles and 1,2,4-Triazole-3-thiones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7104 - 7116

Published: May 4, 2023

A photocatalytic chemodivergent reaction for the selectivity formation of C-S and C-N bonds in a controlled manner was proposed. The medium, either neutral or acidic, is critical to dictate 2-amino-1,3,4-thiadiazoles 1,2,4-triazole-3-thiones from isothiocyanates hydrazones. This practical protocol achieve chemoselectivity under mild metal-free conditions.

Language: Английский

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Manganese-Catalyzed Cycloalkene Ring Expansion Synthesis of Azaheterocycles

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 2, 2024

Herein, a Mn catalytic protocol has been developed for the cycloalkene ring expansion synthesis of azaheterocycles, allowing broad-substrate-scope access to pyridine and isoquinoline derivatives. The initial monoaddition an azidyl radical alkene further as-generated C-radical addition O

Language: Английский

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