Recent Advances in Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions: Exploration of Catalytic Systems, Reaction Parameters, and Ligand Influences: A Review

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123569 - 123569

Published: Feb. 1, 2025

Language: Английский

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ortho‐Selective Suzuki Coupling of Dichlorophenol and Dichlorobenzylalcohol in Water under Palladium Catalysis Directed by Noncovalent Interactions and Computational Analysis

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 14, 2025

Abstract The use of attractive noncovalent interactions is emerging as a versatile approach to address site‐selectivity challenges. Herein, we report ortho‐selective Suzuki coupling reactions in water 2,3‐dichloroarenes and 2,4‐dichloroarenes bearing hydroxy group the presence palladacycle catalyst directed by interactions. Various ortho‐substituted arylphenols arylbenzyl alcohols were obtained good excellent yields with high selectivity. Density functional theory (DFT) calculations ab initio molecular dynamics (AIMD) simulations suggested that ortho ‐selective dichlorophenols dichlorobenzyl occurred through electrostatic hydrogen bonding interactions, respectively.

Language: Английский

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Fluorescent pyridine phosphonium salts via transmutation of metallabenzenes

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 16, 2025

Metallabenzenes are recognized as a unique class of aromatic compounds, not only structural and theoretical interest but also platforms to design powerful transformations. Here, we report the successful transmutation metallabenzene for pyridine synthesis. This 'metal-to-nitrogen swapping' process utilizes readily available ruthenabenzene phosphonium salts commercially 2-aminopyridines under mild conditions. The isolation ruthena-azepines, containing planar seven-membered aza-metallacycle, along with DFT calculations, supports nitrogen insertion/metal deletion cascade driven by aromatization. Additionally, investigate tunable photophysical properties resulting salts.

Language: Английский

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Hyper-Cross-Linked Pyridine-Functionalized Bis(imino)acenaphthene-N-heterocyclic Carbene (BIAN-NHC) Palladium Catalysts for Superior Suzuki–Miyaura and Buchwald–Hartwig Coupling Reactions

ACS Applied Polymer Materials, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

The design and synthesis of a series palladium-loaded hyper-cross-linked polymer (HCP) catalysts, demonstrating high catalytic activity excellent cycling stability in Suzuki–Miyaura Buchwald–Hartwig coupling reactions is reported. By employing pyridine-functionalized BIAN-NHC as the building unit, HCPs with rich hierarchical pore structures surface areas were prepared. Notably, HCP-BIAN-Pd-2 exhibited superior achieved 99% yield less reactive benzyl chloride, maintaining 95% even after 10 cycles. This study addresses issues cost, toxicity, recyclability associated traditional homogeneous palladium significantly enhancing by selectively introducing ligands. These findings highlight immense potential these catalysts for large-scale production practical applications, underscoring their significant implications field heterogeneous catalysis.

Language: Английский

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Synthesis of Methylated, Hydroxylated, and Aminated Metallaaromatics via Ring-Opening Reactions of the Fused Three-Membered Ring Units

Organometallics, Journal Year: 2024, Volume and Issue: 43(13), P. 1472 - 1481

Published: June 14, 2024

The development of efficient functionalization methods for metallaaromatics is pivotal in manipulating their structural and chemical properties. While introducing hydroxyl amino moieties into highly desirable, relevant reports remain scarce. In our approach, we exploit the reaction hydroxylamine with a fused compound composed metallapentalene moiety an unsaturated three-membered metallacycle. Upon exposure to air, oxidized by heating forms nitrosyl anion that replaces chloride ligand within this system. exchange triggers ring opening metallacycles, which then followed protonation, thereby generating series methylated, hydroxylated, aminated metallaaromatic derivatives. This sequential process accompanied dearomatization rearomatization frameworks, demonstrating versatility new methodology.

Language: Английский

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Nano-Pd/Chitosan Composite: An Extremely Effective Catalyst to the Synthesis of Pyrazolyl Analogues through Suzuki–Miyaura Cross-Coupling Reactions in an Aqueous Medium

Journal of Chemistry, Journal Year: 2023, Volume and Issue: 2023, P. 1 - 12

Published: June 27, 2023

Substituted pyrazolyl derivatives were synthesized through Suzuki cross coupling of aromatic boronic acid with heterocyclic halide using newly nano-Pd/chitosan catalyst by the water-mediated green synthesis methodology. The reactivity nano-Pd was highly enhanced incorporating palladium nanoparticles a biopolymer chitosan matrix. studied thoroughly for its structure, morphology, and other fundamental aspects such as size shape various techniques including XRD, FESEM, EDAX analyses. scope disclosed their great stability remarkable reusability cross-coupling reaction twelve different acids under synthetic

Language: Английский

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Carbonylation Reactions of a Metallapentalyne: Synthesis of Its Ester and Amide Derivatives

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(22), P. 2765 - 2772

Published: July 14, 2024

Comprehensive Summary Carbonylation reactions are a valuable synthetic method to construct carbonyl compounds and carbonylation of aryl halides stand out as highly significant tool for generating substituted arenes. However, the important have never been realized in aromatic metallacycles. Herein, we present first metallaaromatics, specifically alkoxycarbonylation aminocarbonylation an osmapentalyne. During process, electronic steric properties nucleophiles regarded critical factors. The alcohols with bulky substituents (isopropanol) require more reaction time tert ‐butyl alcohol is inert reaction. Comparatively, amines, being stronger nucleophiles, exhibit divergent behaviors. Bulky amines undergo aminocarbonylation, whereas small prefer direct nucleophilic additions. Control experiments revealed that intermediate derived from coupling metal carbyne CO plays role According these observations, pathway proposed. Furthermore, photophysical carbonyl‐functionalized osmapentalene complexes studied, maximum absorption peak compound carboxylic group exhibits red‐shift due smaller HOMO‐LUMO gap. These findings contribute expanding reactivity metallaaromatics offer new opportunities synthesis

Language: Английский

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Palladium(II) and Platinum(II) Complexes Bearing ONS-Type Pincer Ligands: Synthesis, Characterization and Catalytic Investigations

Molecules, Journal Year: 2024, Volume and Issue: 29(14), P. 3425 - 3425

Published: July 22, 2024

This work describes the synthesis of eight new Pd(II) and Pt(II) complexes with general formula [M(TSC)Cl], where TSC represents 4N-monosubstituted thiosemicarbazone derived from 2-acetylpyridine N-oxide substituents CH

Language: Английский

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