Stereoselective Three-Component Carbocyclization of 1,7-Enynes with Sulfoxonium Ylides and Water under Photoredox Catalysis

Organic Letters, Год журнала: 2024, Номер 26(31), С. 6736 - 6741

Опубликована: Июль 29, 2024

A visible-light-induced photoredox three-component carbocyclization reaction of 1,7-enynes with sulfoxonium ylides and water is reported. The protocol provides a facile entry to structurally valuable highly functionalized cyclopenta[c]quinoline scaffolds in chemoselective stereoselective manner. Salient features this method include redox-neutral conditions, no requirement base or other additive, good functional-group tolerance.

Язык: Английский

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Ru(II)-Catalyzed Carboamination of Olefins with α-Carbonyl Sulfoxonium Ylides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5382 - 5391

Опубликована: Апрель 1, 2024

The first ruthenium-catalyzed carboamination of olefins with α-carbonyl sulfoxonium ylides is reported. utilization an inexpensive ruthenium catalyst enables the concise synthesis pharmaceutically important isoindolin-1-ones, which possess both a stereogenic center and β-carbonyl side chain. This method mild, efficient, scalable allows for coupling wide range aryl-, heteroaryl-, alkenyl-, alkyl-substituted ylides. Moreover, carbonyl chain in resulting product provides good handle downstream transformations. For mechanistic studies, ruthacyle complex obtained proven to be key intermediate catalytic stoichiometric reactions.

Язык: Английский

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I₂-Promoted Chemoselective Annulative Coupling of 2-Aminobenzamides with Sulfoxonium Ylides: Easy Access to Quinazolinones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12410 - 12420

Опубликована: Авг. 20, 2024

A flexible and metal-free synthetic approach for synthesizing 2-benzoyl quinazolinones 2-aryl via molecular iodine-mediated annulative coupling of sulfoxonium ylides with 2-aminobenzamides has been disclosed. The method demonstrates remarkable chemoselectivity efficiency, leading to high yields under optimized conditions. broad substrate scope, scalability, practical utility were highlighted through diverse applications, including gram-scale reactions the synthesis biologically significant compounds such as tryptanthrin chemo/biosensor derivative.

Язык: Английский

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Mild Catalyst- and Additive-Free Three-Component Synthesis of 3-Thioisoindolinones and Tricyclic γ-Lactams Accelerated by Microdroplet Chemistry

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

Опубликована: Окт. 3, 2024

Isoindolinones, bearing both γ-lactam and aromatic rings, draw extensive interest in organic, pharmaceutical, medicinal communities as they are important structural motifs many natural products, bioactive compounds, pharmaceuticals. As the main contributor to isoindolinone synthesis, metal catalysis is associated with drawbacks including essential use of toxic/precious metals excessive additives, high reaction temperatures, specially predesigned starting materials, long times (typically 8-30 h). In this study, we developed a catalyst- additive-free, minute-scale, high-yield microdroplet method for tricomponent synthesis at mild temperatures. By taking advantage astonishing acceleration (1.9 × 10

Язык: Английский

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Recent approaches for the synthesis of heterocycles from amidines via metal catalyzed C-H functionalization reaction

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(25), С. 5014 - 5031

Опубликована: Янв. 1, 2024

Transition metal catalyzed C-H bond activation has become one of the most important tools for constructing new chemical bonds. Introducing directing groups to substrates is key a successful reaction, these can also be further transformed in reaction. Amidines with their unique structure and reactivity are ideal transition metal-catalyzed transformations. This review describes major advances mechanistic investigations activation/annulation tandem reactions amidines until early 2024, focusing on unsaturated compounds, such as alkynes, ketone, vinylene carbonate, cyclopropanols derivatives. Meanwhile this manuscript explores reaction different carbene precursors, example diazo azide, triazoles, pyriodotriazoles, sulfoxonium ylides well own activation/cyclization reactions. A bright outlook provided at end manuscript.

Язык: Английский

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Reactions with sulfoxonium ylides using metal-catalysis

Advances in organometallic chemistry, Год журнала: 2024, Номер unknown, С. 227 - 286

Опубликована: Янв. 1, 2024

Язык: Английский

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Annulative Coupling of β‐Ketosulfoxonium Ylides and β‐Ketothioamides: Access to Thiazolines and Thiazolidin‐4‐Ones

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(19), С. 4073 - 4077

Опубликована: Июль 3, 2024

Abstract A catalyst‐ and additive‐free one‐step protocol for synthesizing thiazolines thiazolidin‐4‐ones, utilizing the annulative coupling between β‐ketosulfoxonium ylides β‐ketothioamides has been described. The dual functionalization of through S‐alkylation intramolecular N‐cyclization leads to generation both C−S C−N bonds. developed synthetic methods facilitate synthesis diverse functionalized thiazolidin‐4‐one derivatives, validated large‐scale reactions.

Язык: Английский

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Construction of isoindolin-1-ones via tandem reaction of ester-functionalized aziridines with amines

Synthetic Communications, Год журнала: 2024, Номер unknown, С. 1 - 8

Опубликована: Ноя. 21, 2024

We have developed a tandem reaction of ester-functionalized aziridines with secondary amines for the construction isoindolin-1-ones. Its mechanism involves sequential ring opening and lactamization. The novel features this include high efficiency, broad substrate scope mild conditions.

Язык: Английский

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Rh(III)-Catalyzed Aminoalkylation of Alkenes with Diazo Compounds toward Functionalized Isoindolinones

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(11), С. 3505 - 3505

Опубликована: Янв. 1, 2024

Язык: Английский

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