Recent progress in the organoselenium-catalyzed difunctionalization of alkenes

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Selenium-based catalysts have recently been utilized to facilitate a variety of new organic transformations, owing their intrinsic advantages, including low cost, toxicity, stability in both air and water, strong compatibility with diverse functional groups. The difunctionalization alkenes-the process incorporating two groups onto carbon-carbon double bond-has garnered particular interest within the chemical community its significant applications synthesis. Recently, organoselenium-catalyzed alkenes has emerged as an ideal powerful route obtain high-value vicinal difunctionalized molecules. This review emphasizes recent advancements this rapidly evolving field, focusing on scope, limitations, mechanisms various reactions.

Language: Английский

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Transition-metal-free phosphorylation of polyfluoroarenes with P(O)H compounds

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: 23(10), P. 2358 - 2361

Published: Jan. 1, 2025

Herein, a base-promoted C-P(O) bond formation method has been developed for the phosphorylation of polyfluoroarenes through selective C-F cleavage. The high selectivity and mild, transition-metal-free conditions this underscore its potential sustainable synthesis applications. This expands scope polyfluoroarene functionalization, providing valuable tool incorporating phosphorus motifs in complex aromatic frameworks.

Language: Английский

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Synthesis of novel 2-alkyl and 2-aryl 4-phosphorylated oxazolines from dimethyl (±)-phosphoserinate

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134471 - 134471

Published: Feb. 1, 2025

Language: Английский

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One-Pot Synthesis of Novel Tetrasubstituted α-Aminophosphonates Derived from α-Methylphosphoserine and In Vivo Evaluation as Anti-Inflammatory Agents

Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 18, 2025

A series of new tetrasubstituted α-aminophosphonate derivatives with a methylphosphoserine fragment were described. These compounds synthesized by three-component (3-CR) "Kabachnik-Fields reaction." The novel α-aminophosphonates screened for in vivo anti-inflammatory activity through topical and oral administration routes. All decreased TPA-induced ear edema dose-dependent fashion. In this test, 2, 5, 7 showed the same efficacy (≈ 90%) higher potency than indomethacin inflammatory marker neutrophil-to-lymphocyte ratio (NLR). Moreover, pretreatment post-treatment 2-7 reduced CFA-induced paw edema, as did or (S)-naproxen. Based on promising results, we investigated their physicochemical pharmacokinetics profiles silico. analysis also revealed that not break Lipinski's rule five had drug-likeness favorable ADME properties transdermal administration.

Language: Английский

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In Situ Coordination-Catalyzed o-Vanillin Underwent a One-Pot Tandem Reaction to Construct Complex Chiral Tetrameric Isomer-Based Hexanuclear Clusters

Inorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

In this work, Dy(NO3)3·6H2O and o-vanillin reacted under "one-pot" conditions, achieving for the first time four efficient condensations of obtaining a pair chiral hexanuclear clusters R/S-Dy6. The Dy(III) ions in structure R/S-Dy6 are arranged planar quadrilateral with ion derived from each upper lower ends, forming shape similar to "chair". complex ligands H4LR1 H4LS1 were obtained simple through multistep tandem reaction. Their formation process involved series reaction steps, including free radical coupling form pinacol an situ o-vanillin. Magnetic studies show that have magnetic anisotropy and/or low excited states. addition, has outstanding ability produce reactive oxygen species low-power light irradiation shows excellent photodynamic sterilization. inhibition zones against Escherichia coli about 2.09 2.99 cm, Staphylococcus aureus 2.51 2.93 respectively. This work not only provides vivid example synthesis organic products but also promotes progress lanthanide clusters' crystal engineering.

Language: Английский

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Bridging Homogeneous and Heterogeneous Catalysis: Ni@CPOL-dppp&PPh₃-Catalyzed Symmetric H-Phosphonate Diester Synthesis from Sodium Hypophosphite

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7912 - 7918

Published: April 29, 2025

Language: Английский

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Studies on the electrochemical reactions of 1-amino phosphonates

Electrochemistry Communications, Journal Year: 2025, Volume and Issue: unknown, P. 107944 - 107944

Published: May 1, 2025

Language: Английский

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Access to Chiral Oxindoles via Ir-Catalyzed Asymmetric Pudovik Addition/[1,2]-Phospha-Brook Rearrangement/Allylation Cascade

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 2, 2025

An asymmetric catalytic Pudovik addition/[1,2]-phospha-Brook rearrangement/allylation reaction of readily available isatins, phosphites, and vinyl ethylene carbonate enabled by a chiral iridium catalyst was developed in one-pot fashion. A wide range enantioenriched oxindole derivatives containing two adjacent stereocenters could be obtained good to high yields with excellent diastereoselectivity enantioselectivity (65-99% yield, 7:1 >20:1 dr, generally 99% ee). This cascade protocol owned the advantages starting materials, regio-/diastereo-/enantioselectivity, substrate scope generality.

Language: Английский

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Synthesis of Diversely Substituted Diethyl (Pyrrolidin-2-Yl)Phosphonates

Molecules, Journal Year: 2025, Volume and Issue: 30(9), P. 2078 - 2078

Published: May 7, 2025

Imidazoline I2 receptors (I2-IR) are untapped therapeutic targets lacking a structural description. Although the levels of I2-IR dysregulated in plethora illnesses, arsenal ligands that can modulate is limited. In this framework, we have reported several new families embodying iminophosphonate functional group an excellent affinity and selectivity for I2-IR, selected members demonstrated relevant pharmacological properties murine models neurodegeneration Alzheimer’s disease. Starting with these iminophosphonates, continued to exploit their high degree functionalization through short efficient synthesis access unprecedented 2,3-di, 2,2,3-tri, 2,3,4-tri, 2,2,3,4-tetrasubstituted diethyl (pyrrolidine-2-yl) phosphonates. The stereochemistry compounds was unequivocally characterized by X-ray crystallographic analyses. Two features shared starting products were pharmacologically evaluated, allowing us deduce required key motifs biologically active aminophosphonate derivatives.

Language: Английский

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Photoinduced [4 + 2] Cycloaddition of Dienes and Quinonemethides

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A visible light-induced photoinduced cycloaddition of 1,3-dienes and p -quinonemethides is reported. The reaction proposed to proceed through an EDA complexation pathway with no external photocatalyst, oxidant or additives being used.

Language: Английский

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