85614-82-0

Upstream product

• 696-62-8 para-iodoanisole 
• 108-44-1 1-amino-3-methylbenzene 
• 620-25-7 N-(3-methylphenyl)hydroxylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 99-08-1 1-methyl-3-nitrobenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 108-39-4 3-methyl-phenol 
• 17933-03-8 m-tolylboronic acid 
• 104-94-9 4-methoxy-aniline 
• 591-24-2 3-Methylcyclohexanone 
• 108-41-8 1-chloro-3-methylbenzene 
• 591-17-3 meta-bromotoluene 

Downstream Products

• 220716-53-0 N-(4'-bromo-1,1'-biphenyl-4-yl)-N-(4-methoxyphenyl)-N-(3-methylphenyl)amine 
• 433716-28-0 3-[4-(4-methoxy{4'-[4-methoxy(3-methylphenyl)anilino][1,1'-biphenyl]-4-yl}anilino)phenoxy]propyl methacrylate 
• 464216-90-8 3-[4-(4-methoxy{4'-[4-methoxy(3-methylphenyl)anilino][1,1'-biphenyl]-4-yl}anilino)phenoxy]propan-1-ol 
• 865479-92-1 (4-methoxy-phenyl)-m-tolyl-(4-vinyl-phenyl)-amine 

Relevant academic research and scientific papers

Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines

The development and study of a simple copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic investigations established that the cross-coupling reaction proceeds via a nitrosoarene intermediate and that copper is required to catalyze both the deoxygenation of the nitroarene to afford the nitrosoarene and C-NAr bond formation of the nitrosoarene with the aryl boronic acid.

METHOD FOR PRODUCING AROMATIC AMINE COMPOUNDS FROM PHENOLS

PROBLEM TO BE SOLVED: To provide a method for producing an aromatic amine compound from phenols and amines with a high yield and a high selectivity, which includes ones subjected to polyfunctionalization, under relatively low temperature and relatively low pressure, without using an additive which gives a co-product having high environmental load. SOLUTION: Phenols and hydrogen are introduced into a first catalyst cartridge receiving a solid catalyst containing platinum group elements and continuously hydrogenated into cyclohexanones. The resultant cyclohexanones, along with amines selected from ammonia, primary amines and secondary amines, and hydrogen trapping agents are subsequently introduced into a second catalyst cartridge receiving a solid catalyst containing platinum group elements to continuously produce aromatic amine compounds by dehydration condensation and dehydrogenation with amines. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2021,JPOandINPIT

Continuous Synthesis of Aryl Amines from Phenols Utilizing Integrated Packed-Bed Flow Systems

Aryl amines are important pharmaceutical intermediates among other numerous applications. Herein, an environmentally benign route and novel approach to aryl amine synthesis using dehydrative amination of phenols with amines and styrene under continuous-flow conditions was developed. Inexpensive and readily available phenols were efficiently converted into the corresponding aryl amines, with small amounts of easily removable co-products (i.e., H2O and alkanes), in multistep continuous-flow reactors in the presence of heterogeneous Pd catalysts. The high product selectivity and functional-group tolerance of this method allowed aryl amines with diverse functional groups to be selectively obtained in high yields over a continuous operation time of one week.

Cu-ACP-Am-Fe3O4@SiO2: an efficient and recyclable heterogeneous catalyst for the Chan–Lam coupling reaction of boronic acids and amines

Abstract: We have developed an efficient method for Cu-ACP-Am-Fe3O4@SiO2 catalyzed Chan–Lam coupling of phenylboronic acid with primary amine furnished secondary amines. The catalyst offered virtues like mild reaction conditions, magnetically separable, and reusable and exhibits excellent performance in terms of good product yield and high turnover number. Graphic abstract: [Figure not available: see fulltext.]

Palladium-catalyzed aerobic dehydrogenative aromatization of cyclohexanone imines to arylamines

Dehydrogenative aromatization of cyclohexanone imines to arylamines has been achieved using a palladium catalyst under aerobic conditions. The reaction is applicable to a variety of imines that are either preformed or generated in situ from cyclohexanone derivatives and aryl or alkylamines.

Smiles rearrangement for the synthesis of diarylamines

A protocol for the one-pot synthesis of diarylamines via Smiles rearrangement under microwave irradiation has been developed. Various diarylamines were effectively synthesized starting from readily available substituted phenols, arylamines and chloroacetyl chloride in moderate to good yields (58-92%). ARKAT-USA, Inc.

Synthesis of diarylamines catalyzed by iron salts

A study was conducted to demonstrate the synthesis of diarylamines catalyzed by iron salts. The study evaluated the influence acetyl as an N-protecting group. The coupling of acetanilide and iodobenzene was selected as a model reaction, to optimize the reaction conditions. It was observed that a considerable amount of the N-deprotected compound was obtained along with the desired N-acetyl diarylamine. It was also observed that diphenylamine was isolated in a significant yield, by performing a basic hydrolysis with NaOMe after the iron-catalyzed arylation. A one-pot synthesis of diphenylamine was performed by adding NaOMe to the N-arylation reaction mixture, after the acetanilide was consumed completely. It was demonstrated that the strategy overcomes the synthetic limitations associated with poor reactivity of aromatic amines under iron catalysis and serves as an alternative approach for the preparation of diarylamines.

Synthesis of oxygenated carbazoles by palladium-mediated oxidative double C-H activation of diarylamines assisted by microwave irradiation

Microwave irradiation in the presence of palladium acetate and traces of dimethylformamide allows the fast and efficient cyclodehydrogenation of diphenylamines into carbazoles. The scope of the microwave-assisted reaction is broader than that of the one using conventional conditions in that it allows the preparation of oxygenated carbazoles without apparent loss in yield. The applicability of the method to the preparation of carbazole alkaloids has been demonstrated by the development of a total synthesis of murrayafoline A, which proceeds in 50% overall yield from commercially available materials and is the shortest and most efficient route for the preparation of this alkaloid to date. Georg Thieme Verlag Stuttgart.

Unexpected multicomponent reaction of 2/4-methoxyarylaldehydes with arylhydroxylamines and maleic anhydride: a novel synthesis of unsymmetrical diarylamines

Unsymmetrical diarylamines have been synthesized by a novel, unexpected multicomponent reaction between methoxyarylaldehydes, N-arylhydroxylamine and maleic anhydride. A possible mechanism for the formation of the product is proposed. The reaction was also carried out under microwave irradiation.

Designing interfaces that function to facilitate charge injection in organic light-emitting diodes

Layer-by-layer (LbL) assembly of triarylamine (TAA)-containing polymers has been applied for anode functionalizations in organic light-emitting diodes (OLEDs). Surface work function of the ITO electrodes was significantly altered with the functionalizatio