The Carbene Chemistry of N-Sulfonyl Hydrazones: The Past, Present, and Future

Chemical Reviews, Год журнала: 2025, Номер unknown

Опубликована: Янв. 10, 2025

N-Sulfonyl hydrazones have been extensively used as operationally safe carbene precursors in modern organic synthesis due to their ready availability, facile functionalization, and environmental benignity. Over the past two decades, there has tremendous progress chemistry of N-sulfonyl presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Many transfer reactions are unique cannot be achieved by any alternative methods. The discovery novel development highly enantioselective new skeletal editing represent notable recent achievements hydrazones. This review describes overall made hydrazones, organized based on reaction types, spotlighting current state-of-the-art remaining challenges addressed future. Special emphasis is devoted identifying, describing, comparing scope limitations methodologies, key mechanistic scenarios, potential applications complex molecules.

Язык: Английский

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Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Язык: Английский

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Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile

Organics, Год журнала: 2024, Номер 5(2), С. 46 - 58

Опубликована: Апрель 2, 2024

Recently, the construction of trisubstituted olefin-type probe molecules has elicited attention many researchers. However, synthesis probes containing two N-heterocycles simultaneously been rarely reported. In this study, starting from inexpensive mucobromic acid 1 and N-heterocyclic compound 2, we first utilized a simple one-step reaction to synthesize series compounds 3 bearing with structure rings in absence transition metal catalysts yield 62–86%. The optimal conditions were systematically explored, obtained well characterized 1H NMR, 13C X-ray single-crystal HR-MS. preliminary observation showed that, presence base, reacts as its ring-opening structure, successive nucleophilic substitution Michael addition can generate target product 3. Considering that aldehyde group molecular may react malononitrile, carried out some relevant investigations so realize visual detection malononitrile. Interestingly, among products, 3a–3c be prepared portable test strips through process used achieve naked-eye malononitrile environmental systems designed.

Язык: Английский

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Platform of Oxidative Transformation of α-Methyl Secondary Enaminones toward Tetrahydropyridines

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

Опубликована: Март 20, 2025

In this paper, the application of α-methyl secondary enaminones in synthesis tetrahydrofuropyridines is described. The key step methodology situ generation 1-azadiene from oxidation enaminone, followed by a subsequent inverse-electron-demand hetero-Diels–Alder reaction proceeded to give desired product. Mechanistic studies and density functional theory (DFT) calculations revealed detailed pathway. Gram-scale preparation experiments further transformation product demonstrate potential applicability method. addition, amide derivatives could be obtained employing β-methyl as substrates under similar oxidative conditions. present work opens new window rarely reported enaminones.

Язык: Английский

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Rhodium-catalyzed synthesis of N-substituted 3-acylpyrroles from enaminones and vinylene carbonate

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 12, 2024

We developed a cascade C–H activation/[3 + 2] annulation for enaminones and vinylene carbonate, employing the catalyst [Cp*RhCl 2 ] oxidants. This reaction allows efficient synthesis of 3-carbonylpyrroles.

Язык: Английский

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Histidine-derivate modified Cu/SiO2 catalyst for selective hydrogenation of dimethyl oxalate to methyl glycolate

Fuel, Год журнала: 2024, Номер 381, С. 133701 - 133701

Опубликована: Ноя. 15, 2024

Язык: Английский

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Synthesis of Functionalized Indoles by an Iridium-Catalyzed N–H Insertion Cascade: Nucleophilic Cyclization of Naphthylamines with α-Diazocarbonyl Compounds

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 28, 2024

A novel iridium-catalyzed [3 + 2] annulation of naphthylamines and α-diazocarbonyl compounds was developed for the rapid assembly densely functionalized indoles. This new catalytic process represents first example a cascade intramolecular nucleophilic cyclization by N-H insertion amines. Various could be obtained in high yields with excellent functional group tolerance. The reaction affords valuable indole derivatives, enabling expedient access to heterocyclic analogues not easily accessible other methods.

Язык: Английский

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A copper-catalyzed annulation reaction of diazo esters with propargyl amines for the synthesis of 2,5-dihydropyrroles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(16), С. 4546 - 4555

Опубликована: Янв. 1, 2024

An efficient protocol for the synthesis of 2,5-dihydropyrroles using diazo esters and propargyl amines has been reported, featuring mild reaction conditions, straightforward operation, absence metal ligands, high atom economy.

Язык: Английский

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