34160-17-3

Usage

InChI:InChI=1/C17H15N/c1-18(15-10-3-2-4-11-15)17-13-7-9-14-8-5-6-12-16(14)17/h2-13H,1H3

Upstream product

• 90-30-2 N-phenyl-1-naphthylamine 
• 74-88-4 methyl iodide 
• 21792-52-9 1,2-diethynylbenzene 
• 100-61-8 N-methylaniline 
• 86-56-6 N,N-dimethyl-1-naphthalenamine 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 99747-74-7 1-naphthyl triflate 
• 86-57-7 1-Nitronaphthalene 
• 4004-51-7 tri-1-naphthyl phosphate 
• 124-38-9 carbon dioxide 
• 96-54-8 N-Methylpyrrole 
• 90-11-9 1-Bromonaphthalene 
• 90-13-1 1-Chloronaphthalene 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 305818-95-5 4-[N-(4-Dibromophosphino-1-naphthyl)-N-methylamino]phenylphosphinothioic dimorpholide 
• 305818-55-7 [4-(di-morpholin-4-yl-phosphinothioyl)-phenyl]-methyl-naphthalen-1-yl-amine 

Relevant academic research and scientific papers

1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines

ortho-Amino difunctionalization of aryl triflates has been achieved via a three-component reaction. The cascade reaction proceeds through a zincate base-mediated deprotonative formation of a reactive aryne intermediate, in situ nucleophilic addition, and coupling with electrophilic partners. This strategy leverages the advantageous reactivity of organozincate intermediates, enabling the installation of various functionalities such as amine, azide, oxygen, sulfur, halide, alkynyl, aryl, vinyl, and alkyl groups in a modular manner for the synthesis of diverse aniline skeletons.

Method for catalyzing nitro-arene and amine compound to be synthesized into aromatic amine compounds through palladium/imidazolium salt

The invention discloses a method for catalyzing nitro-arene and an amine compound to be synthesized into aromatic amine through palladium/imidazolium salt. The method comprises the steps that in an organic solvent, the palladium/imidazolium salt is taken as a catalyst, the nitro-arene and the amine compound are subjected to a coupling reaction under the function of alkali, and then the aromatic amine compounds are obtained through aftertreatment. The method is simple in ligand synthesis, storage is facilitated, the price is low, the use quantity of ligands is low, the yield of the product is high, and the substrates have high applicability and are suitable for preparing diarylamine and N-alkylated arylamine. The method can be used for synthesizing a series of aromatic amine compounds, andthe aromatic amine compounds have high application value in the fields of pesticides, medicines, materials and the like.

Well-Designed N-Heterocyclic Carbene Ligands for Palladium-Catalyzed Denitrative C-N Coupling of Nitroarenes with Amines

The C-N bond formation is one of the fundamental reactions in organic chemistry, because of the widespread presence of amine moieties in pharmaceuticals and biologically active compounds. Palladium-catalyzed C-N coupling of haloarenes represents one of the most efficient approaches to aromatic amines. Nitroarenes are ideal alternative electrophilic coupling partners, since they are inexpensive and readily available. The denitration and cross-coupling using nitroarenes as the electrophilic partners is challenging, because of the low reactivity of the Ar-NO2 bond toward oxidative addition. We report here the C-N coupling of nitroarenes and amines using palladium/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily available from commercial chemicals. The reaction shows broad substrate scope and functional group tolerance. The method is applicable to both aromatic and aliphatic amines, and many secondary and tertiary aromatic amines bearing various functional groups were obtained in high yields.

Palladium-catalyzed c(sp2)-n bond cross-coupling with triaryl phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

Palladium-Catalyzed C(sp2)-N Bond Cross-Coupling with Triaryl Phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(?-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

Solvent-free mechanochemical Buchwald-Hartwig amination of aryl chlorides without inert gas protection

A solvent-free Buchwald-Hartwig amination had been developed under high-speed ball-milling conditions, which afforded the desired products with moderate to high yields. The addition of sodium sulfate was found to be crucial for improving both the performance and the reproducibility. Comparative solvent-free stirring experiments implicated the importance of mechanical interaction for the transformation, and the inert gas was proved to be unnecessary for this amination.

1,4-Dioxane-Tuned Catalyst-Free Methylation of Amines by CO2 and NaBH4

A catalyst-free reductive functionalization of CO2 with amines and NaBH4 was developed. The N-methylation of amines was carried out with CO2 as a C1 building block and 1,4-dioxane as the solvent. Notably, the six-electron reduction of CO2 to form the methyl group occurred simultaneously with formation of the C?N bond to give the N-methylated amine.

Biphenyl sulfonic acid ligands for catalytic C-N cross coupling of aryl halides with anilines and secondary amines

The use of two biphenyl sulfonic acid ligands for the catalytic C-N cross coupling of aryl halides with anilines, 3-aminopyridine, and secondary amines is reported. Our results represent a significant improvement compared to state of the art methods especially with regards to the removal of palladium.

A mechanical to urge the enters the carbon - [...] forming method (by machine translation)

The invention discloses a mechanical to urge the enters the carbon - [...] forming method, said method comprising: in order to type 2 shown in formulae of organic amine 3 shown the chlorinated aromatic hydrocarbon as the raw material, the catalyst, ligand, in the presence of alkali and additive, the reaction is carried out by the mechanical grinding method, after the reaction mixture after the separation and purification, obtains the type 1 compound shown; in the present invention relates to mechanical grinding promotion to the chlorinated aromatic hydrocarbon as the substrate of the Buchwald - Hartwig reaction mainly adopts the organic phosphonate ligands, in the palladium catalyst under the action of the organic amine compound with the chlorinated aromatic hydrocarbon of the between the coupling, so as to obtain high yield of the target product, the majority of the reaction can be 90% or more yield. The mild reaction conditions, can be in the 1 - 2 H to complete the reaction. (by machine translation)

Solvent-free Buchwald-Hartwig reaction of aryl and heteroaryl halides with secondary amines

A highly efficient solvent-free protocol for the Buchwald-Hartwig amination of (hetero)aryl halides by secondary amines was developed. The reaction is mediated by a Pd(OAc)2/RuPhos catalytic system in air. Various (hetero)aryl halides were coupled with diaryl, alkyl-aryl, and dialkylamines in good to excellent yields (51 examples, 50-99% yield). Copyright