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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Synthesis of condensed tetra- and polycyclic nitrogen heterocycles with a five-membered azacyclic core induced by ionic palladium catalysts

Coordination Chemistry Reviews, Год журнала: 2024, Номер 504, С. 215668 - 215668

Опубликована: Янв. 19, 2024

Язык: Английский

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Palladium-Catalyzed Enantioselective Intramolecular Heck Dearomative Annulation of Indoles with N-Tosylhydrazones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(22), С. 15881 - 15893

Опубликована: Ноя. 3, 2023

An elegant Pd(dba)2-catalyzed enantioselective Heck dearomative annulation of indoles and N-tosylhydrazones for the straightforward assembly structurally diverse optically active indoline scaffolds containing quaternary carbon centers at C2 position has been developed. The tandem protocol, which utilized a Pd(dba)2/BINOL-based phosphoramidite ligand as catalytic system, proceeded smoothly through successive oxidative addition, intramolecular palladation, migratory insertion, β-elimination sequences, leading to chiral derivatives in moderate excellent yields, with enantioselectivities diastereoselectivities. In synthetic practicability system was underlined by scaled-up experiment late-stage derivatization products, thus highlighting potential applications chemistry, medicinal material science.

Язык: Английский

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Heck Macrocyclization in Forging Non-Natural Large Rings including Macrocyclic Drugs

International Journal of Molecular Sciences, Год журнала: 2023, Номер 24(9), С. 8252 - 8252

Опубликована: Май 4, 2023

The intramolecular Heck reaction is a well-established strategy for natural product total synthesis. When constructing large rings, this also referred to as macrocyclization, which has proved viable avenue access diverse naturally occurring macrocycles. Less noticed but likewise valuable, it created novel macrocycles of non-natural origin that neither serve nor derive from products. This review presents systematic account the title in forging subset thereby addressing topic rarely covered literature. Walking through two complementary sections, namely (1) drug discovery research and (2) synthetic methodology development, demonstrates beyond well-known domain synthesis, macrocyclization plays remarkable role forming macrocycles, particular macrocyclic drugs.

Язык: Английский

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Synthesis of Cyclopenta[c]quinolines by Palladium-Catalyzed Cyclization of 3-Bromoindoles with Internal Alkynes via Spirocyclic Cyclopentadiene Intermediates

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8984 - 8991

Опубликована: Июнь 20, 2023

A novel method for the construction of a cyclopenta[c]quinoline ring via cyclization 3-bromoindoles with internal alkynes in presence palladium is described. The formation proposed from double [1,5] carbon sigmatropic rearrangement spirocyclic cyclopentadiene intermediate, which generated situ involving sequential alkyne insertion into carbon–palladium bond and dearomatization indole. present studies have developed ring-expansion reaction pyrrole to pyridine one C2–C3 indoles provided simple distinct route tricyclic fused-quinoline derivatives that are not easy access conventional methods.

Язык: Английский

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Palladium-catalyzed cascade cyclization of α,β-unsaturated N-tosylhydrazones with iodoarenes : access to 2H-chromenes and 2H-quinolines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(46), С. 9121 - 9124

Опубликована: Янв. 1, 2024

A palladium-catalyzed cascade reaction of α,β-unsaturated N -tosylhydrazones with iodoarene derivatives containing a nucleophilic group is described.

Язык: Английский

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