Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(4), P. 1364 - 1416

Published: Jan. 17, 2023

Hypervalent aryliodoumiums are intensively investigated as arylating agents. They excellent surrogates to aryl halides, and moreover they exhibit better reactivity, which allows the corresponding arylation reactions be performed under mild conditions. In past decades, acyclic aryliodoniums widely explored However, unmet need for is improvement of their notoriously low reaction economy because coproduced iodides during often wasted. Cyclic have intrinsic advantage in terms economy, started receive considerable attention due valuable synthetic applications initiate cascade reactions, can enable construction complex structures, including polycycles with potential pharmaceutical functional properties. Here, we summarizing recent advances made research field cyclic aryliodoniums, nascent design aryliodonium species applications. First, general preparation typical diphenyl iodoniums described, followed by heterocyclic monoaryl iodoniums. Then, initiated arylations coupled subsequent domino summarized construct polycycles. Meanwhile, building biaryls axial atropisomers discussed a systematic manner. Finally, very advance employed halogen-bonding organocatalysts described.

Language: Английский

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Organocatalyzed Phospha‐Michael Addition: A Highly Efficient Synthesis of Customized Bis(acyl)phosphane Oxide Photoinitiators

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 29(1)

Published: Oct. 6, 2022

Abstract Addition of the P−H bond in bis(mesitoyl)phosphine, HP(COMes) 2 (BAPH), to a wide variety activated carbon–carbon double bonds as acceptors was investigated. While this phospha‐Michael addition does not proceed absence an additive or catalyst, excellent results were obtained with stoichiometric basic potassium caesium salts. Simple amine bases can be employed catalytic amounts, and tetramethylguanidine (TMG) particular is outstanding catalyst that allows preparation bis(acyl)phosphines, R−P(COMes) , under very mild conditions yields after only short time. All phosphines RP(COMes) subsequently oxidized corresponding bis(acyl)phosphane oxides, RPO(COMes) substance class belonging most potent photoinitiators for radical polymerizations known date. Thus, simple highly atom economic method has been found broad range adapted their specific field application even on large scale.

Language: Английский

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Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

International Journal of Molecular Sciences, Journal Year: 2022, Volume and Issue: 23(15), P. 8819 - 8819

Published: Aug. 8, 2022

An enzymatic route for phosphorous-carbon bond formation was developed by discovering new promiscuous activity of lipase. We reported a metal-free biocatalytic method the synthesis pharmacologically relevant β-phosphonomalononitriles via lipase-catalyzed one-pot Knoevenagel-phospha-Michael reaction. carefully analyzed best conditions given reaction: type enzyme, temperature, and solvent. A series target compounds synthesized, with yields ranging from 43% to 93% reaction Candida cylindracea (CcL) lipase as recyclable and, few times, reusable catalyst. The advantages this protocol are excellent yields, mild conditions, low costs, sustainability. applicability same catalyst in β-phosphononitriles is also described. Further, obtained were validated potential antimicrobial agents characteristic E. coli bacterial strains. pivotal role such group phosphonate derivatives on inhibitory against selected pathogenic strains revealed. observed results especially important case increasing resistance bacteria various drugs antibiotics. impact β-phosphono malonate chemical structure demonstrated. crucial substituents attached aromatic ring action Among tested compounds, four β-phosphonate showed an profile similar that currently used antibiotics ciprofloxacin, bleomycin, cloxacillin. In addition, constitute convenient platform further functionalization, allowing change their biological profile. It should be noted cost low, which may attractive alternative agents. because

Language: Английский

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Phospha-Michael addition of biphenylphosphine oxide to chalcones and α,β-unsaturated esters using the organocatalyst 1,1-diaminobenzalazine

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 122, P. 154505 - 154505

Published: April 21, 2023

Language: Английский

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New Horizon in Phospha-Michael Reaction: Ultrafast Double Addition of P–H Bond-Bearing Nucleophiles to Electron-Deficient Triple Bonds and Its Use for Functional Monomer Synthesis and Polymer Modification

Macromolecules, Journal Year: 2023, Volume and Issue: 56(17), P. 7006 - 7022

Published: Aug. 22, 2023

In this work, a novel, straightforward, robust, fast, and organocatalyst-mediated phospha-Michael reaction (OCPMR) was developed for the addition of phosphorus nucleophiles to electron-deficient alkynes. Several P–H bond-bearing compounds with either fully aliphatic or aromatic units were utilized newly reaction, it found that phosphorous species containing only groups reacted activated alkynes within 5 min at room temperature. The led fast double-addition triple bond An in-depth analysis mechanism selectivity OCPMR performed using computational methods. Using method, double-phosphorylated allyl-functional monomers synthesized subsequently used synthesis linear crosslinked polymers via thiol-ene photopolymerization. thermoset materials exhibited LOI values as high 26.4%. We also showed polyesters having bonds could be easily functionalized compounds. synthetic method proposed herein promises easy P–C formation under mild conditions, is straightforward phosphorus-containing monomers, polymers, polymer post-functionalization. believe feature will great interest not material chemists scientists but organic chemists, pharmaceutical researchers, etc.

Language: Английский

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Lipase-Catalyzed Phospha-Michael Addition Reactions under Mild Conditions

Molecules, Journal Year: 2022, Volume and Issue: 27(22), P. 7798 - 7798

Published: Nov. 12, 2022

Organophosphorus compounds are the core structure of many active natural products. The synthesis these is generally achieved by metal catalysis requiring specifically functionalized substrates or harsh conditions. Herein, we disclose phospha-Michael addition reaction biphenyphosphine oxide with various substituted β-nitrostyrenes benzylidene malononitriles. This biocatalytic strategy provides a direct route for C-P bonds good functional group compatibility and simple practical operation. Under optimal conditions (styrene (0.5 mmol), Novozym 435 (300 U), EtOH (1 mL)), lipase leads to formation organophosphorus in yields up 94% at room temperature. Furthermore, confirm role catalytic triad this reaction. new system will have broad applications organic synthesis.

Language: Английский

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A selective turn-on fluorescent chemosensor 1,1-diaminoazine for azinphos-methyl

Journal of Photochemistry and Photobiology A Chemistry, Journal Year: 2022, Volume and Issue: 437, P. 114476 - 114476

Published: Dec. 6, 2022

Detection of organophosphorus pesticides (OPPs) is an important challenge in environmental chemistry, because their exposure to humans can cause severe health problems. In the current study, organic nanoparticles (E)-(4-chlorophenyl)-1,1-diamino-2,3-diazabutadiene were developed using eco-friendly approach which was found be range 15–20 nm. These synthesized species exhibited both U.V. Visible and "turn-on" fluorescence responses aqueous media for selective detection extremely hazardous pesticide azinphos-methyl. also exhibit a good linear relationship 1–100 μM limit (LOD) 7.4 µM. The response observed RO water, tap water orange juice. FT-IR DFT studies helped identifying specific H-bonding interactions responsible Azinphos-methyl.

Language: Английский

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Copper (I) Catalysed Tandem C−C and C−N Bond Cleavage of N‐Fused Imidazoles towards the Synthesis of N‐pyridinylamides

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(13)

Published: April 3, 2023

Abstract Copper(I) catalysed oxidative conversion of imidazopyridines into N‐pyridinylamides has been achieved via tandem C−C and C−N bond cleavages under reaction conditions. The methodology wide substrate scope products were formed in good to excellent yields. This method is suitable for the both C‐3 functionalized as well non‐functionalized

Language: Английский

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Michael addition reaction of malonates with nitro-olefins catalyzed by 1,1-diaminoazine, a bifunctional hydrogen bonding organocatalyst

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(43), P. 19983 - 19986

Published: Jan. 1, 2023

Carbon–carbon bond forming processes are central to synthetic organic chemistry, and the Michael addition reaction is a frequently used method for C–C formation; 1,1-diaminoazines have been utilised as organocatalysts facilitate this reaction.

Language: Английский

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Synthesis of Oxazolines using Aldol/Cyclization Cascade Reactions Employing 1,1‐Diaminobenzalazine as Organocatalyst

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(44)

Published: Nov. 1, 2024

Abstract 1,1‐Diaminobenzalazine has been recently reported to catalyze different types of Michael addition reactions; this organic molecule unique characteristic features for bifunctional organocatalysis. Organocatalysts were shown be useful in aldol/cyclization cascade reactions, it is important establish whether 1,1‐diaminobenzalazine can employed the reactions. In work, synthesis oxazolines with help organocatalyst, 1,1‐diaminobenzalazine, reported. This method relatively more efficient, cost‐effective, and environmentally safe as avoids use metal oxides co‐catalysts.

Language: Английский

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