15383-71-8

Upstream product

• 100-52-7 benzaldehyde 
• 104-86-9 4-chlorobenzylamine 
• 100-46-9 benzylamine 
• 100-51-6 benzyl alcohol 
• 100-42-5 styrene 
• 100-47-0 benzonitrile 
• 50777-76-9 (2-formylphenyl)(diphenyl)phosphine 
• 622-95-7 4-chlorobenzyl bromide 
• 17332-59-1 N-(4-chloro-benzyl)-phthalamic acid 
• 130517-96-3 N-(4-chlorobenzylidene)benzylamine 
• 141-52-6 sodium ethanolate 
• 623-03-0 4-Cyanochlorobenzene 

Downstream Products

• 87419-19-0 3,4-diphenyl-1-(p-chlorobenzyl)-3-hydroxyazetidin-2-one 
• 87419-19-0 3,4-diphenyl-1-(p-chlorobenzyl)-3-hydroxyazetidin-2-one 
• 104-88-1 4-chlorobenzaldehyde 
• 104-86-9 4-chlorobenzylamine 
• 183963-74-8 [(4-Chloro-benzylamino)-phenyl-methyl]-phosphonic acid diethyl ester 
• 130517-96-3 N-(4-chlorobenzylidene)benzylamine 
• 20441-11-6 N-benzyl-1-(4-chlorophenyl)-N-methylmethanamine 

Relevant academic research and scientific papers

Iridium(I) Complexes Bearing a Noninnocent PNP-Pincer-Type Phosphaalkene Ligand: Catalytic Application in the Base-Free N-Alkylation of Amines with Alcohols

A series of IrI complexes [Ir(L)(PPEP?)] [L = Cl- (3), CO (4), tBuNC (5), PMe3 (6), PPh3 (7)], coordinated with a PNP-pincer-type phosphaalkene ligand bearing a dearomatized pyridine ring (PPEP?), have been prepared and their catalytic properties for the dehydration/condensation of amines with alcohols has been examined. The catalytic reactions successfully proceed under base-free conditions to give N-alkylated amines and their dehydrogenation derivatives (imines). The product selectivity is dependent on L coordinated with Ir(PPEP?). Complexes 4 and 5 that contain π-accepting ligands (CO, tBuNC) form N-alkylated amines as the major products in a closed system using a nitrogen-gas-filled Schlenk tube. In contrast, complex 7 that contain PPh3 as L produces imines as the major products under a nitrogen-gas flow. The reason for the selectivity change depending on L is discussed based on stoichiometric reactions using model compounds of presumed catalytic intermediates. PNP-pincer-type phosphaalkene complexes of IrI bearing a dearomatized pyridine ring have been found to catalyze the dehydration/condensation of amines with alcohols under base-free conditions to afford N-alkylated amines and imines in high yields. The product selectivity can be controlled by the choice of auxiliary ligands (L) as well as the reaction conditions.

Formation of 2-Azaallyl Cobalt(I) Complexes by Csp3-H Bond Activation

Three novel unsymmetrical η3-2-azaallyl cobalt(I) complexes, [(2-PPh2)C6H4]CHN[CHC6H4(4-R)]Co(PMe3)2 (4-6) (R = H (4); Cl (5); and OMe (6)), were synthesized by the r

Polyoxometalate-Supported Aminocatalyst for the Photocatalytic Direct Synthesis of Imines from Alkenes and Amines

Developing efficient photocatalysts for direct oxidative coupling of alkenes and amines with O2 under mild conditions is very significant. Herein, ZnW-PYI is well-designed by assembling a [PZnW11O39(H2O)]5- photooxidation catalyst and chiral aminocatalyst pyrrolidine-2-ylimidazole (PYI) via a coordination model. ZnW-PYI efficiently catalyzed the synthesis of imines from alkenes and amines using O2 as the oxidant through nucleophilic catalysis by employing pyrrolidine as an organocatalyst. Combining a polyoxometalate and PYI within one single framework is an effective approach not only for stabilization and heterogenization of the redox-active catalyst and aminocatalyst but also for realization of compatibility between the reaction intermediates and synergy of multiple catalytic cycles.

Highly efficient microwave assisted synthesis of magnetically separable GO-CoFe2O4 nanocomposite for visible light induced oxidative coupling of benzyl amines

The present paper describes an efficient microwave-assisted synthesis of magnetic CoFe2O4 and its nanocomposite with graphene oxide (GO-CoFe2O4) for photocatalytic oxidative coupling of benzylamines to the corresponding imines using molecular oxygen. The surface morphologies and structures of both CoFe2O4 and GO-CoFe2O4 nanocomposites were investigated by various spectroscopic techniques including powder X-ray diffraction (XRD), Transmission electron microscopy (HR-TEM), Fourier transform infrared spectroscopy (FTIR), nitrogen adsorption–desorption isotherms, X-ray photoelectron spectroscopy (XPS) and Raman Spectroscopy. Photocatalytic oxidative coupling experiments demonstrated that GO-CoFe2O4 exhibited significantly higher efficiency than CoFe2O4 nanoparticles, suggesting that GO played an important role in the reaction. Moreover, the magnetic nature of the synthesized nanocomposite provided facile recovery of the material by the influence of an external magnet.

Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines

Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.

Half-Sandwich Ruthenium Complexes Bearing Hemilabile κ2-(C,S)?Thioether-Functionalized NHC Ligands: Application to Amide Synthesis from Alcohol and Amine

Amide synthesis is one of the most crucial transformations in chemistry and biology. Among various catalytic systems, N-heterocyclic carbene (NHC)-based ruthenium (Ru) catalyst systems have been proven to be active for direct synthesis of amides by sustainable acceptorless dehydrogenative Coupling of primary alcohols with amines. Most often, these catalytic systems usually use monodentate NHC and thus require an additional ligand to obtain high reactivity and selectivity. In this work, a series of cationic Ru(II)(η6-p-cymene) complexes with thioether-functionalized N-heterocyclic carbene ligands (imidazole and benzimidazole-based) have been prepared and fully characterized. These complexes have then been used in the amidation reaction and the most promising one (i. e. 3 c) has been applied on a large range of substrates. High conversions albeit with moderate yields have generally been obtained.

Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines

The commercially available and bench-stable Co(acac)2/dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.

A Resin-Bound Peptoid as a Recyclable Heterogeneous Catalyst for Oxidation Reactions

Reusable solid-grafted catalysts have environmental and economical advantages over soluble catalysts. Numerous catalysts, including peptides, were immobilized on solid supports to enable their recyclability. Nevertheless, the few catalytic peptoids – N-substituted glycine oligomers – reported to date were only used off-resin. The soluble peptoids BT and DI, a trimer and dimer having two catalytic side-chains, were developed as bio-inspired oxidation catalysts. BT has an additional structure-directing group, which enables intramolecular cooperativity between the two catalytic groups (“intra-peptoid” mode). Thus, it catalyzes the oxidation of primary alcohols with much higher efficiency than DI. Herein, we present resin-bound BT and DI (TG-BT and TG-DI) as the first insoluble and recyclable catalytic peptoids. We discovered that though TG-BT also operates through the intra-peptoid cooperativity mode, it is less efficient than BT, even after several cycles. On the other hand, TG-DI is far more active than DI and can be recycled several times to enable a much higher turn-over-number. Our studies revealed that TG-DI operates through an intra-resin cooperativity mode, and this enables its high activity compared with DI, BT and TG-BT.

Synthesis of Secondary Aldimines from the Hydrogenative Cross-Coupling of Nitriles and Amines over Al2O3-Supported Ni Catalysts

A heterogeneous Ni catalyst was discovered to be active in the synthesis of secondary cross-imines via hydrogenative coupling of nitriles and amines. The mesoporous Al2O3-supported Ni nanoparticles (abbreviated as Ni/m-Al2O3-600, where 600 represents the reduction temperature) were active in hydrogenative coupling of nitriles and amines reaction at 80 °C and 1 bar H2, affording corresponding cross-imines with yields in the range 64.1-98.1%. Density functional theory calculations reveal the hydrogenation of benzonitrile (PhCN) to benzylamine (PhCH2NH2) has higher activation energy than that for hydrogenative cross-coupling of PhCN and RNH2 on the Ni/m-Al2O3-600 catalyst, suggesting the latter reaction is more favorable. The theoretical calculations are in good agreement with our experimental results.

Hydrogenated Cu2OAu@CeO2 Z-scheme catalyst for photocatalytic oxidation of amines to imines

The design and fabrication of highly active visible light photocatalysts for organic synthesis reactions are particularly challenging for solar energy utilization and conversion. Herein, hydrogenated Z-scheme yolk-shell Cu2OAu@CeO2 (H-Cu2OAu@CeO2) photocatalysts were synthesized using cubic Cu2O as the starting core material via surface Au deposition and oxidation etching process, followed by hydrogenation treatment. When compared with CeO2, Cu2O@CeO2, and Cu2O@CeO2Au nanocomposites, optimized H-Cu2OAu@CeO2 showed remarkably higher visible light oxidation activity for the synthesis of imines from amines at ambient pressure and room temperature. The remarkably enhanced photoactivity of the H-Cu2OAu@CeO2 composite mainly derives from the enhanced photoinduced charge separation efficiency, porous yolk-shell structure, proper surface defects, and well-maintained strong oxidation/reduction capabilities. The Z-scheme charge transfer process and photocatalytic reaction mechanism of the H-Cu2OAu@CeO2 composites were also provided through spectral and photoelectrochemical analyses together with the investigation of structure and photocatalytic oxidation reactions. This study provides a probable approach for designing unique Z-scheme catalysts.