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

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(11), С. 2830 - 2848

Опубликована: Янв. 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.

Язык: 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, Год журнала: 2023, Номер 365(22), С. 3855 - 3860

Опубликована: Окт. 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.

Язык: 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, Год журнала: 2025, Номер unknown

Опубликована: Май 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.

Язык: Английский

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Radical strategies for chemodivergent cyclization reactions

Trends in Chemistry, Год журнала: 2023, Номер 5(12), С. 906 - 919

Опубликована: Ноя. 7, 2023

Язык: Английский

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Iodine-Mediated C2,3–H Aminoheteroarylation of Indoles

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(21), С. 15106 - 15117

Опубликована: Окт. 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.

Язык: 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, Год журнала: 2023, Номер 88(19), С. 14140 - 14155

Опубликована: Сен. 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.

Язык: Английский

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A microwave-assisted intramolecular aminopalladation-triggered domino sequence: an atom economical route to 5,10-dihydroindeno[1,2-b]indoles

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(15), С. 3121 - 3131

Опубликована: Янв. 1, 2023

A microwave-assisted, palladium(II)-catalyzed cascade reaction of 2-alkynylanilines tethered with an α,β-unsaturated carbonyl moiety was established to access 5,10-dihydroindeno[1,2-b]indoles in high yields (up 84%) a short time. This operationally simple process shows 100% atom economy and allows the construction two new five-membered rings (1 C-C 1 C-N) bonds single synthetic attempt. The mechanistic pathway this is visualized involving intramolecular aminopalladation (5-endo-dig) followed by carbopalladation (olefin insertion) protonolysis steps. systematic comparison between microwave irradiation conventional heating methods also performed demonstrate supremacy microwave-assisted approach. domino requires no protecting groups for amino group palladium catalyst needs ligands. To best our knowledge, first report on nucleopalladation-initiated transformation.

Язык: Английский

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

Chinese Chemical Letters, Год журнала: 2023, Номер 35(4), С. 108902 - 108902

Опубликована: Авг. 9, 2023

Язык: 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, Год журнала: 2023, Номер 88(11), С. 7104 - 7116

Опубликована: Май 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.

Язык: Английский

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Cascade Electrochemical Aerobic Oxygenation of 2-Substituted Indoles and Electrochemical [5 + 3] Annulation with Amidines: Access to Eight-Membered Benzo[1,3,5]triazocin-6(5H)-ones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4673 - 4683

Опубликована: Март 13, 2024

The cascade electrochemical C3-selective aerobic oxygenation of 2-substituted indoles and [5 + 3] annulation with amidines through an undivided cell galvanostatic method employing molecular oxygen "electricity" as green oxidants was developed. This protocol provides efficient direct approach to eight-membered benzo[1,3,5]triazocin-6(5H)-ones. Mechanistic studies suggested that two subsequent processes both proceeded radical pathways.

Язык: Английский

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