10282-32-3

Upstream product

• 17224-21-4 1-(4-cyanophenyl)-N-phenylmethanimine 
• 100-39-0 benzyl bromide 
• 873-74-5 4-Aminobenzonitrile 
• 10278-46-3 N-(4-cyanophenyl)benzamide 
• 100-52-7 benzaldehyde 
• 623-00-7 4-bromobenzenecarbonitrile 
• 100-46-9 benzylamine 
• 3058-39-7 4-iodobenzonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 18523-41-6 4-azidobenzonitrile 
• 108-88-3 toluene 
• 626201-15-8 4-cyanophenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 830325-00-3 3-(4-cyano-phenyl)-4-oxo-3,4-dihydro-quinazoline-2-carboxylic acid ethyl ester 
• 767-00-0 4-cyanophenol 

Downstream Products

• 153982-19-5 N-trifluoroacetyl-4-benzylaminobenzonitrile 
• 143490-33-9 Benzyl-(4-cyano-phenyl)-dithiocarbamic acid methyl ester 
• 143490-24-8 4-(Benzyl-trifluoromethyl-amino)-benzonitrile 
• 849806-04-8 N-(4-aminomethyl-phenyl)-benzylamine 
• 518071-13-1 p-(benzylamino)benzaldehyde 
• 1254190-55-0 [(4-cyanophenylamino)phenylmethyl]phosphonic acid diethyl ester 
• 17224-21-4 1-(4-cyanophenyl)-N-phenylmethanimine 

Relevant academic research and scientific papers

d-Glucose: An Efficient Reducing Agent for a Copper(II)-Mediated Arylation of Primary Amines in Water

A copper-catalyzed Ullmann-type amination with primary amines in water with a combination of copper(II) triflate [Cu(OTf)2], dipivaloylmethane, and d-glucose is reported. The mild conditions and the use of an inexpensive catalyst as well as a renewable feedstock (d-glucose and the surfactant TPGS-750-M, which is derived from vitamin E) make this protocol a safe and convenient strategy for efficient C?N bond formation. This easy-to-handle procedure is extremely competitive compared to palladium-based reactions and may be used to synthesize N-containing molecules, such as drugs or organic light-emitting diodes (OLEDs).

Photocatalytic secondary amine synthesis from azobenzenes and alcohols on TiO2 loaded with Pd nanoparticles

Photoirradiation (λ > 300 nm) of TiO2 loaded with Pd nanoparticles (ca. 2 wt%, 5 nm diameter) in water containing alcohols and azobenzene derivatives at room temperature successfully produces the corresponding secondary amines with high yields.

Mechanistic investigation of the iridium-catalysed alkylation of amines with alcohols

The [Cp*IrCl2]2-catalysed alkylation of amines with alcohols was investigated using a combination of experimental and theoretical methods. A Hammett study involving a series of para-substituted benzyl alcohols resulted in a line with a negative slope. This clearly documents that a positive charge is built up in the transition state, which in combination with the measurement of a significant kinetic isotope effect determines hydride abstraction as being the selectivity-determining step under these conditions. A complementary Hammett study using para-substituted anilines was also carried out. Again, a line with a negative slope was obtained suggesting that nucleophilic attack on the aldehyde is selectivity-determining. A computational investigation of the entire catalytic cycle with full-sized ligands and substrates was performed using density functional theory. The results suggest a catalytic cycle where the intermediate aldehyde stays coordinated to the iridium catalyst and reacts with the amine to give a hemiaminal which is also bound to the catalyst. Dehydration to the imine and reduction to the product amine also takes place without breaking the coordination to the catalyst. The fact that the entire catalytic cycle takes place with all the intermediates bound to the catalyst is important for the further development of this synthetic transformation. The Royal Society of Chemistry 2012.

One-pot reductive amination of carbonyl compounds with nitro compounds with CO/H2O as the hydrogen donor over non-noble cobalt catalyst

The one-pot reductive amination of carbonyl compounds with nitro compounds over heterogeneous non-noble metal catalysts was developed for the first time by transfer hydrogenation with CO/H2O as the hydrogen donor. Nitrogen-doped carbon supported cobalt nanoparticles were observed to be active toward this reaction, affording structurally-diverse secondary amines with high yields. Kinetic studies revealed that the transfer hydrogenation of imines (C[dbnd]N bonds) was the rate-determining step. Reaction mechanism studies indicated that both nitrogen and cobalt nanoparticles were important for the transfer hydrogenation with CO/H2O to generate the proton (N[sbnd]H+) and hydride (Co[sbnd]H?) as the active species. Furthermore, the heterogeneous cobalt catalyst was highly stable without the loss of its catalytic activity during the recycling experiments.

Heterogeneous cobalt catalysts for reductive amination with H2: General synthesis of secondary and tertiary amines

Heterogeneous Co@NC catalysts were prepared, characterized and applied for the reductive amination of aldehydes and ketones with H2 gas. The Co catalyst Co@NC (800-2 h) was found to be active and selective for the reductive amination of aldehydes and ketones using H2 gas. Thus, general synthesis of secondary and tertiary amines was developed by the Co-catalyzed reductive amination with H2 gas, and various secondary and tertiary amines can be obtained in high yields. Moreover, a practical synthesis of N-substituted isoindolinones was also presented by a one step process with the Co@NC (800-2 h) catalyst. The Co@NC (800-2 h) catalyst is reusable at least five times without evident loss of activity.

Copper-catalyzed coupling of alkylamines and aryl iodides: an efficient system even in an air atmosphere.

[reaction: see text] A mild method for the copper-catalyzed amination of aryl iodides is reported. This operationally simple C-N bond-forming protocol uses CuI as the catalyst and ethylene glycol as ligand in 2-propanol. A variety of functionalized aryl iodides as well as several amines were efficiently coupled using this method. This catalytic amination procedure is relatively insensitive to moisture and can be performed under an air atmosphere with comparable yield. Preliminary results on the amination of aryl bromides are also described.

Amination of alcohols catalyzed by copper-aluminium Hydrotalcite: A green synthesis of amines

Copper-aluminium hydrotalcite (CuAl-HT)/K2CO3 has been employed in the activation of various benzyl alcohols with benzylamines to afford the corresponding amines in good to high yields. Experimentation showed that the reaction takes place through sequential transformations: the oxidation of alcohols into carbonyl compounds, imine formation between amines and carbonyl compounds, and then reduction of imines to amines, heterogeneously catalyzed by non-noble Cu-Al HT catalyst in a one-pot and straightforward fashion. The process was further extended to amination of alcohols with anilines, which are often resistant to alkylation reactions when substituted with strong electron-withdrawing groups.

Cobalt encapsulated in N?doped graphene sheet for one-pot reductive amination to synthesize secondary amines

To develop an efficient base-metal reductive amination catalyst for synthesis of secondary amines is still a major challenge. In this study, an efficient N-doped graphene sheet-coated cobalt catalyst (Co@CN-800) was developed through a simple pyrolysis process, which could gave 99.5 % yield of N-benzylaniline by one-pot reductive amination of nitrobenzene with benzaldehyde during at least 5 cycles. Catalyst characterization and control experiments confirmed that the robust catalytic performance of the catalyst is probably due to the synergy effect of in situ generated Co-Nx encapsulated in N?doped graphene layer and appropriate meso-pore structure. Additionally, The substrate adaptability of the catalyst was proved since a variety of corresponding secondary amines were smoothly obtained under relatively mild conditions, which makes the secondary amine synthesis strategy based on Co@CN-800 shows excellent application prospect.

Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines

A novel intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-one derivatives induced by base treatment and its application to the expeditious synthesis of secondary aryl amines, including diaryl amines, are descri

A recyclable Cu/Al-HT catalyst for amination of aryl chlorides

A simple Cu/Al-HT catalyzed amination of aryl chlorides with primary and secondary aromatic amines has been developed. This ligand-free heterogeneous Cu/Al-HT catalyst, in conjunction with base, also efficiently works for the amination of aryl chlorides with cycloalkylamines. This method tolerates a variety of functional groups and does not require an expensive additive.