5459-79-0

Upstream product

• 106-49-0 p-toluidine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 100-51-6 benzyl alcohol 
• 106-43-4 para-chlorotoluene 
• 103-49-1 dibenzylamine 
• 106-38-7 para-bromotoluene 
• 100-52-7 benzaldehyde 
• 99-99-0 1-methyl-4-nitrobenzene 
• 5405-15-2 N-benzyl-N-(4-methylphenyl)amine 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 380481-66-3 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane 
• 5720-05-8 4-methylphenylboronic acid 
• 620-05-3 iodomethylbenzene 

Downstream Products

• 139399-33-0 3-benzyl-6-methylbenzo[d]thiazol-2(3H)-imine 
• 1266679-84-8 N,N-dibenzyl-5-methylbiphenyl-2-amine 
• 100-52-7 benzaldehyde 
• 582-78-5 N-(4-methylphenyl)benzamide 
• 1355025-49-8 N,N-dibenzyl-4-methyl-2-((triisopropylsilyl)ethynyl)aniline 

Relevant academic research and scientific papers

Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- And Dialkylated Amines

Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested that the Ir(III)-H was the active intermediate in this reaction. KIE study revealed that the breaking of the C-H bond of alcohol might be the rate-limiting step. Notably, this solvent-free strategy disclosed a high TON of around 5600. Based on kinetic studies and control experiments, a metal-ligand cooperative mechanism was proposed.

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions

Herein, an efficient and green method for the selective synthesis of tertiary amines has been developed that involves iridium-catalyzed alkylation of various primary amines with aromatic or aliphatic alcohols. Notably, the catalytic protocol enables this transformation in the absence of additional base and solvent. Furthermore, the alkylation of nitrobenzene with primary alcohol to tertiary amine has also been achieved by the same catalytic system. Deuterium-labeling experiments and a series of control experiments were conducted, and the results suggested that an intermolecular borrowing hydrogen pathway might exist in the alkylation process.

Balancing Bulkiness in Gold(I) Phosphino-triazole Catalysis

The syntheses of a series of 1-phenyl-5-phosphino 1,2,3-triazoles are disclosed, within which, the phosphorus atom (at the 5-position of a triazole) is appended by one, two or three triazole motifs, and the valency of the phosphorus(III) atom is completed by two, one or zero ancillary (phenyl or cyclohexyl) groups respectively. This series of phosphines was compared with tricyclohexylphosphine and triphenylphosphine to study the effect of increasing the number of triazoles appended to the central phosphorus atom from zero to three triazoles. Gold(I) chloride complexes of the synthesised ligands were prepared and analysed by techniques including single-crystal X-ray diffraction structure determination. Gold(I) complexes were also prepared from 1-(2,6-dimethoxy)-phenyl-5-dicyclohexyl-phosphino 1,2,3-triazole and 1-(2,6-dimethoxy)-phenyl-5-diphenyl-phosphino 1,2,3-triazole ligands. The crystal structures thus obtained were examined using the SambVca (2.0) web tool and percentage buried volumes determined. The effectiveness of these gold(I) chloride complexes to serve as precatalysts for alkyne hydration were assessed. Furthermore, the regioselectivity of hydration of but-1-yne-1,4-diyldibenzene was probed.

Direct reductive coupling of nitroarenes and alcohols catalysed by Co-N-C/CNT@AC

A non-noble heterogeneous catalyst-a Co, N and C composite encapsulated carbon nanotube grown in situ on the surface of activated carbon (Co-N-C/CNT@AC)-was fabricated via the pyrolysis-reduction process. Co-N-C/CNT@AC catalyzed the reductive coupling of structurally diverse nitroarenes and alcohols to imines and secondary amines under exogenous base- and solvent-free conditions. BET, TEM, SEM, XRD and XPS characterization showed that the exceptional catalytic property of Co-N-C/CNT@AC could be explained by its nanostructure, Co-N and basic N species. Our protocol had advantages of low cost, environment-friendliness, and good applicability. Furthermore, a reaction route of nitroarenes, amines and alcohols as the starting materials was proposed to improve the atom economy of the reductive coupling of nitroarenes with alcohols.

Copper-catalyzed electrophilic amination using: N -methoxyamines

Copper-catalyzed electrophilic amination of a triarylboroxin using an N-methoxyamine to give quick access to a variety of anilines was reported. The reaction was especially useful for syntheses of functionalized anilines when combined with our previously reported nucleophilic addition to N-methoxyamides.

Method of producing higher amine (by machine translation)

PROBLEM TO BE SOLVED: To provide a method of producing a secondary or tertiary higher amine. SOLUTION: The method of producing a higher amine comprises allowing a primary or secondary amine to react with an alcohol in the presence of at least one species of hydrogen halide selected from hydrogen chloride, hydrogen bromide and hydrogen iodide, or in the presence of a compound capable of producing a hydrogen halide (such as 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-chloride). If the raw material amine is a primary amine, a secondary higher amine and a tertiary higher amine can be produced. If the raw material amine is a secondary amine, a tertiary higher amine can be produced. COPYRIGHT: (C)2012,JPO&INPIT

Metal-free reductive amination of aldehydes for the synthesis of secondary and tertiary amines

Reductive amination of aldehydes to produce secondary amines at room-temperature by in situ generated benzimidazoline is discussed. The bonus of the reaction is the formation of pharmaceutically important benzimidazole as a by-product in good yield, which can be recovered from the reaction mixture by simple filtration. The product, secondary amine, is transformed to tertiary amine in the same pot.

Copper-Catalyzed Electrophilic Amination of Organoaluminum Nucleophiles with O -Benzoyl Hydroxylamines

A copper-catalyzed electrophilic amination of aryl and heteroaryl aluminums with N,N-dialkyl-O-benzoyl hydroxylamines that affords the corresponding anilines in good yields has been developed. The catalytic reaction proceeds very smoothly under mild conditions and exhibits good substrate scope. Moreover, the developed catalytic system is also well suited for heteroaryl aluminum nucleophiles, providing facile access to heteroaryl amines.

An expeditious N,N-dibenzylation of anilines under ultrasonic irradiation conditions using low loading Cu(II)-clay heterogeneous catalyst

A simple one-pot procedure for the direct N,N-dibenzylation of anilines using a catalytic amount of Cu modified montmorillonite-KSF is described. Cu modified montmorillonite-KSF has been proven to be a simple, efficient, mild, convenient, and effective catalyst for the selective benzylation of anilines with benzyl bromide. Cu loading plays a significant role in product yield and solvents were found to control the selectivity. The catalyst is easy to prepare, heterogeneous, stable, and easy to recover.