6940-30-3

Usage

Uses

N,N-Diphenylnaphthalen-2-amine is used as a reactant in the synthesis of biaryl diamines.

InChI:InChI=1/C22H17N/c1-3-11-20(12-4-1)23(21-13-5-2-6-14-21)22-16-15-18-9-7-8-10-19(18)17-22/h1-17H

Upstream product

• 135-88-6 N-Phenyl-2-naphthylamine 
• 637-88-7 1,4-Cyclohexanedione 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 580-13-2 2-bromonaphthalene 
• 122-39-4 diphenylamine 
• 90-11-9 1-Bromonaphthalene 
• 1145-08-0 naphthalen-2-yl N,N-dimethylsulfamic acid 
• 7385-85-5 naphthalen-2-yl tosylate 
• 108-90-7 chlorobenzene 
• 17425-91-1 N-(trimethylsilyl)-diphenylamine 
• 91-58-7 2-chloronaphthalene 
• 5856-90-6 sodium diphenylamine 
• 612-55-5 2-iodonaphthalene 

Downstream Products

• 1048378-07-9 N,N,N′,N′-tetraphenyl-1,1′-binaphthalene-2,2′-diamine 
• 1293999-27-5 7-phenyl-benzo[a]acridinium perchlorate 

Relevant academic research and scientific papers

SOLVENT-FREE CROSS-COUPLING REACTION, AND PRODUCTION METHOD USING SAID REACTION

Disclosed is a cross-coupling reaction method which forms a chemical bond selected from C—N, C—B, C—C, C—O and C—S bonds, the method comprising: preparing an aromatic compound (1) having a leaving group;preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic amino compound (2-1), a diboronic acid ester or the like (2-2), an aromatic boronic acid or the like (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; andperforming a cross-coupling reaction of the compound (1) with the compound (2) in the presence of a palladium catalyst, a base and a compound (4) having a carbon-carbon double bond or a carbon-carbon triple bond, in the absence of a solvent.

Electron-Catalyzed Coupling of Magnesium Amides with Aryl Iodides

An electron was found to catalyze the coupling of magnesium diarylamides with aryl iodides giving triarylamines through a radical-anion intermediate. The transformation requires no transition metal catalysts or additives, and a wide array of products are formed in good-to-excellent yields.

Production of the triarylamine

PROBLEM TO BE SOLVED: To provide a method for producing a triarylamine compound by coupling an N, N-dialkyl sulfamate compound and a diaryl amide compound in the presence of a nickel catalyst.SOLUTION: A triarylamine is produced by allowing an N, N-dialkyl sulfamate represented by formula (1) (in the formula, Arrepresents a phenyl group or the like, and Rand Reach independently represents a 1-4C alkyl group that may be substituted with a fluorine atom) to react with a diarylamide in the presence of a nickel catalyst.

Pd-indenyl-diphosphine: An effective catalyst for the preparation of triarylamines

A new Buchwald-type diphosphine ligand has been developed for applications in Pd-catalyzed amination reactions towards the preparation of triarylamines. The catalyst can be used to perform the amination of a diverse array of aryl and heteroaryl chlorides.

Catalytic carbon-nitrogen bond-forming cross-coupling using N-trimethylsilylamines

Carbon-nitrogen bond-forming cross-coupling reaction of haloarenes with N-trimethylsilyl (TMS)-substituted secondary and primary arylamines proceeded with the aid of a palladium catalyst and a fluoride activator. Various TMS-N(aryl)2, TMS-NH(aryl), and TMS-N(alkyl)2 reacted to give the corresponding coupled products in high yields. Multi-TMS-amine nucleophiles such as N,N-(TMS)2-aniline and N,N′-Ph2-N,N′-(TMS)2-p-phenylenediamine also participated in this C-N coupling to give multiply C-N coupled products in high yields. The novel C-N cross-coupling reaction was successfully applied to C-N bond-forming polymerization. Relative rates of the cross-coupling of p-bromotoluene with N-TMS-substituted primary and secondary amines showed that N-TMS-diphenylamine reacted faster than N-TMS-N-methylaniline or N-TMS-aniline, and N-TMS-morpholine was the least reactive, indicating that the low basicity of the nitrogen nucleophile is the key for the smooth coupling.

Silicon-based CN cross-coupling reaction

Palladium-catalyzed CN bond-forming cross-coupling reaction of N-trimethylsilylamines with aryl bromides and chlorides is found to proceed in the presence of a fluoride activator in 1,3-dimethyl-2-imidazolidinone (DMI), giving triarylamines in excellent yields. When aryl bromide and bis(silyl)amine were used in this reaction, double CN bondforming products were obtained in high yields. The present reaction was successfully applied to CN bond-forming polymerization.

Nickel-catalyzed triarylamine synthesis: Synthetic and mechanistic aspects

An improved protocol was described for the amination of chloroarenes with diarylamines under NiCl2(PCy3)2 catalysis in the presence of a Grignard reagent as base. This method fully suits bromo-/iodoarene substrates as well, and even is expanded to certain aryl tosylates. A preliminary investigation into the mechanism suggests that this amination reaction might proceed through NiI and NiIII intermediates rather than via the usually expected Ni0-Ni II cycle.

Simple and convenient methods for N-arylation of heterocycles and diphenylamine

N-Arylation of NH-heterocycles and diphenylamine with various aryl halides, using a readily accessible ligand-free potassium tert-butoxide/iron(III) oxide/dimethyl sulfoxide reagent system, gives the corresponding N-aryl derivatives in 47-97% yields. Georg Thieme Verlag Stuttgart . New York.

Ni-catalyzed arylation of bromomagnesium diarylamides with aryl N,N-dimethylsulfamates

The combination use of Ni(cod)2 and N,N-1,3-bis(2,6- diisopropylphenyl)-4-imidazoline-2-ylidene as a catalyst successfully gave unsymmetrical N,N-diaryl-N′,N′-diphenyl-1,1′-biphenyl-4, 4′-diamines through the arylation of bromomagnesium diarylamide with 1-(4′-diphenylamino-1,1′-biphenylyl) N,N-dimethylsulfamate. This Ni catalyst and Grignard reagents of diaryl or monoarylamides were also useful in the syntheses of various triarylamines and diarylamines from corresponding aryl N,N-dimethylsulfamates. 2012 Elsevier Ltd. All rights reserved.

Iron-catalyzed aromatic amination for nonsymmetrical triarylamine synthesis

Novel iron-catalyzed amination reactions of various aryl bromides have been developed for the synthesis of diaryl- and triarylamines. The key to the success of this protocol is the use of in situ generated magnesium amides in the presence of a lithium halide, which dramatically increases the product yield. The present method is simple and free of precious and expensive metals and ligands, thus providing a facile route to triarylamines, a recurrent core unit in organic electronic materials as well as pharmaceuticals.