2765-24-4

Upstream product

• 855879-70-8 N-[2]naphthyl-N-nitroso-acetamide 
• 98-95-3 nitrobenzene 
• 20893-80-5 naphthalene-2-diazonium chloride 
• 38270-09-6 (E)-2'-hydroxy-4-nitrochalcone 
• 7385-85-5 naphthalen-2-yl tosylate 
• 15922-01-7 potassium 4-nitrobenzoate 
• 636-98-6 p-nitrobenzene iodide 
• 442912-20-1 1,3-dihydro-1,1,3,3-tetramethylnaphth[2,3-c][1,2,5]oxadisilole 
• 586-78-7 para-nitrophenyl bromide 
• 580-13-2 2-bromonaphthalene 
• 24067-17-2 4-nitrophenylboronic acid 
• 1947-33-7 4-nitrobenzenediazonium 4-methylbenzenesulfonate 
• 100-00-5 4-chlorobenzonitrile 
• 32316-92-0 naphthalene-2-boronic acid 

Downstream Products

• 1092390-02-7 4,4,5,5-tetramethyl-2-(4-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane 
• 109810-73-3 acetic acid-(4-[2]naphthyl-anilide) 
• 209848-36-2 2-(4-aminophenyl)naphthalene 
• 54717-54-3 2-(4-nitrophenyl)-1,4-naphthoquinone 

Relevant academic research and scientific papers

Discovery of Biphenyl-Sulfonamides as Novel β- N-Acetyl- d -Hexosaminidase Inhibitors via Structure-Based Virtual Screening

Novel insecticidal targets are always in demand due to the development of resistance. OfHex1, a β-N-acetyl-d-hexosaminidase identified in Ostrinia furnacalis (Asian corn borer), is involved in insect chitin catabolism and has proven an ideal target for insecticide development. In this study, structure-based virtual screening, structure simplification, and biological evaluation are used to show that compounds with a biphenyl-sulfonamide skeleton have great potential as OfHex1 inhibitors. Specifically, compounds 10k, 10u, and 10v have Ki values of 4.30, 3.72, and 4.56 μM, respectively, and thus, they are more potent than some reported nonglycosyl-based inhibitors such as phlegmacin B1 (Ki = 26 μM), berberine (Ki = 12 μM), 2 (Ki = 11.2 μM), and 3 (Ki = 28.9 μM). Furthermore, inhibitory kinetic assessments reveal that the target compounds are competitive inhibitors with respect substrate, and based on toxicity predictions, most of them have potent drug properties. The obtained results indicate that the biphenyl-sulfonamide skeleton characterized by simple chemical structure, synthetic tractability, potent activity, and low toxicity has potential for further development in pest management targeting OfHex1.

Cellulose supported Pd(II) complex catalyzed carbon-carbon bonds formation

Corn-cobs are an agro-industrial waste and composed of cellulose mostly. In this study cellulose was isolated from the waste corn-cobs and modified to polymeric hydroxamic acid palladium complex 1 and characterized by using a variety of spectroscopic methods such as field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The complex 1 exhibited high catalytic activity towards Suzuki and Heck coupling reactions of activated and deactivated aryl halides to give the respective coupling products with high yield. Moreover, the complex 1 was recovered and recycled five times with no considerable loss of catalytic overall performance.

Delineating the Role of Substituents on the Coordination Behavior of Aroylhydrazone Ligands in PdII Complexes and their Influence on Suzuki–Miyaura Coupling in Aqueous Media

Reactions of piperonal aroylhydrazone ligands (HL1–HL4) with [PdCl2(PPh3)2] in CH3OH and CHCl3 afforded four new Pd(II) complexes (1–4) featuring diverse coordination behaviors. These complexes 1–4 were fully characterized by elemental analyses, UV/Visible, FT-IR and 1H/13C NMR spectra. The variant coordination modes of piperonal aroylhydrazone ligands with Pd(II) ion in these complexes were unambiguously confirmed by single-crystal XRD study. Though the ligands HL1–HL4 are of similar nature, one of them (HL4) possessing an electron withdrawing nitro group as substitution in the peripheral part of the hydrazone displayed an uncommon ligation towards the palladium ion. An experimentally observed molecular architects were in turn rationalized by density functional theory (DFT) calculations as well as natural bonding analysis (NBO). All these Pd(II) complexes were evaluated for their catalytic potential towards Suzuki–Miyaura cross-coupling reaction of sterically congested arylboronic acids with (hetero)arylhalides under an open-flask conditions in aqueous media with low catalyst loading. Advantageously, the selected catalyst was active up to five cycles without significant loss in activity.

Atom-efficient Pd-catalyzed cross-couplings of chloroarenes with triarylbismuth reagents

Various Pd-catalyzed protocols have been developed for the atom-efficient cross-coupling of chloroarenes with triarylbismuth reagents. Using the developed protocols, an efficient synthesis of unsymmetrical biaryls in good to excellent yields was achieved by employing electron-deficient chloroarenes and a range of triarylbismuth reagents.

Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides

Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. Mechanistic insights suggest that the o-benzenedisulfonimide anion act as an electron transfer agent and promotes a catalytic cycle which does not require the presence of photocatalysts or external oxidants.

Thioether–NHC-Ligated PdII Complex for Crafting a Filtration-Free Magnetically Retrievable Catalyst for Suzuki–Miyaura Coupling in Water

A new benzimidazolium salt, 1-[benzylaminocarbonylmethyl]-3-(2-phenylsulfanylethyl)-1H-benzimidazolium chloride (L), which is a precursor of a novel thioether-functionalized NHC, has been synthesized by subjecting 1H-benzimidazole to a sequence of reactions with 1,2-dichloroethane, sodium thiophenolate, and N-benzyl-2-chloroacetamide, successively. The moisture/air-insensitive complex [Pd(L–HCl)Cl2] (1) was prepared by the reaction of L with PdCl2. The molecular structure of 1, established by X-ray crystallography, revealed a square-planar geometry around Pd. Complex 1 was screened for Suzuki–Miyaura coupling reactions of various aryl/heteroaryl bromides (yields of up to 94 % in 2 h) in water at room temperature. Furthermore, complex 1 was immobilized onto the surface of aminopropyl-functionalized silica-coated magnetite nanoparticles [NPs, Fe3O4@SiO2-(CH2)3-NH2] by a stepwise modification strategy to develop the heterogeneous magnetically retrievable catalyst Fe3O4@SiO2-1′, in which the amide functionality present in the side-arm of the NHC within the NHC–PdII complex serves as linker. This magnetic nanosupport, bearing palladium complexes incorporating a novel thioether-based NHC ligand that functions in aqueous aerobic medium and can be easily separated, renders Fe3O4@SiO2-1′ a most desirable catalyst for the Suzuki–Miyaura coupling reaction. It was also observed that the catalyst was effective for up to seven cycles and was easily separated from the reaction medium by the use of an external magnet, further increasing its appeal.

Arenediazonium Tosylates (ADTs) as Efficient Reagents for Suzuki-Miyaura Cross-Coupling in Neat Water

A simple, convenient, and environment-friendly procedure for the preparation of substituted biaryls via Suzuki-Miyaura cross-coupling- was developed. The use of arenediazonium tosylates and corresponding boron compounds allows a conversion in neat water in the presence of commercially available Pd(OAc)2 under mild conditions with tolerance to a wide range of functional groups. A procedure particularly useful for the synthesis of di-ortho-substituted biaryls was developed.

Mono- and dinuclear cyclopalladates as catalysts for Suzuki–Miyaura cross-coupling reactions in predominantly aqueous media

Suzuki–Miyaura cross-coupling reactions of aryl halides with arylboronic acids were performed in predominantly aqueous media employing two mono- and two dinuclear cyclopalladated complexes as catalysts. These complexes are [Pd(HL)Cl] (I), [Pd(L)(PPh3)] (II), [Pd2(μ-dppb)(L)2] (III) and [Pd2(μ-dppf)(L)2] (IV); where H2L, dppb and dppf represent 4-methoxy-N′-(mesitylidene)benzohydrazide, 1,4-bis(diphenylphosphino)butane and 1,1′-bis(diphenylphosphino)ferrocene, respectively. The reactions were conducted using potassium carbonate as base in presence of tetrabutylammonium bromide (TBAB) at 70/90 °C in dimethylformamide–water (1:20) mixture. Among the four catalysts used, the dinuclear complex IV turned out to be the most effective and afforded moderate to excellent yields with broad substrate scope.

Polystyrene-supported palladium(II) N,N-dimethylethylenediamine complex: A recyclable catalyst for Suzuki-Miyaura cross-coupling reactions in water

The polystyrene-supported Pd(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermal analysis (TG-DTA). This heterogeneous Pd(II) catalyst works efficiently for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides in aqueous medium. The effect of base, and additives for the C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to five times without significant loss in its catalytic activity.

Polystyrene-supported palladium(II) N,N-dimethylethylenediamine complex: A recyclable catalyst for suzuki-miyaura cross-coupling reactions in water

The polystyrene-supported Pd(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermal analysis (TG-DTA). This heterogeneous Pd(II) catalyst works efficiently for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides in aqueous medium. The effect of base, and additives for the C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to five times without significant loss in its catalytic activity.