17224-21-4

Upstream product

• 100-52-7 benzaldehyde 
• 873-74-5 4-Aminobenzonitrile 
• 100-51-6 benzyl alcohol 
• 619-72-7 4-nitrobenzonitrile 
• 10282-32-3 4-(benzylamino)benzonitrile 
• 108-88-3 toluene 

Downstream Products

• 10282-32-3 4-(benzylamino)benzonitrile 
• 1037751-89-5 C₂₂H₁₇N₃O₃ 
• 1326705-18-3 (1S,2S)-N-(4-cyanophenyl)-1-phenyl-2-(methylsulfenyl)-2-{2-[(S)-p-tolylsulfinyl]phenyl}ethylamine 
• 1326705-19-4 (1S,2R)-N-(4-cyanophenyl)-1-phenyl-2-(methylsulfenyl)-2-{2-[(S)-p-tolylsulfinyl]phenyl}ethylamine 
• 1326705-25-2 (1S,2S)-N-(4-cyanophenyl)-2-(methylsulfenyl)-1,2-diphenylethylamine 
• 1326705-26-3 (1R)-N-(4-cyanophenyl)-1,2-diphenylethylamine 

Relevant academic research and scientific papers

Photocatalytic organic syntheses using a glass-milled microchip

Photocatalytic reactions, typically known as difficult to control due to secondary reactions and involvement of multiple radicals, were demonstrated to be controlled well by optimizing the reaction time and the microchip design. The glass-milled microchip has a good resistivity for the organic solutions and withstands multiple usage more than 100 times. The oxidization and reduction reactions were demonstrated and the flow considerably improved the conversion and yield. Furthermore, an imine synthesis was demonstrated as a multi-step reaction by combination of photocatalytic oxidation and reduction reactions.

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys

Direct synthesis of imines from nitro compounds and biomass-derived carbonyl compounds over nitrogen-doped carbon material supported Ni nanoparticles

The selective synthesis of imines from biomass-derived chemicals over heterogeneous non-noble metal catalysts is of great importance for organic transformation. Herein, non-noble heterogeneous nitrogen-doped carbon supported Ni catalysts (abbreviated as Ni/CN-MgO-T, whereTrepresents the pyrolysis temperature) have been facilely prepared from the simple pyrolysis of Ni precursors and biomass, and Ni/CN-MgO-600 with the smallest size of Ni nanoparticles demonstrated the highest catalytic activity. The reductive coupling of nitroarenes and carbonyl compounds could be performed under mild conditions (80 °C, and 10 bar H2), affording structurally-diverse imines with high to excellent yields (84.2-98.1%). Thanks to the mild reaction conditions, the developed method showed good tolerance to other functional groups such as nitriles, halogen and vinyl groups.

Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis

A visible-light-mediated process for dehydrogenation of amines has been described. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification. This process can be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biologically active molecules. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation.

4,4′-Bipyridyl-Catalyzed Reduction of Nitroarenes by Bis(neopentylglycolato)diboron

4,4′-Bipyridyl worked as an organocatalyst for the reduction of nitroarenes by bis(neopentylglycolato)diboron (B2nep2), followed by hydrolysis to give the corresponding anilines. This reduction proceeded under aerobic conditions without any prepurification of substrates and reagents. We found broad functional group tolerance and compatibility for O- A nd N-protecting groups under the reaction conditions. The key in this catalytic system was the addition of B2nep2 to 4,4′-bipyridyl to form N,N′-bis[(neopentylglycolato)boryl]-4,4′-bipyridinylidene as a deoxygenating reagent of nitroarenes.

Effect of linker and metal on photoreduction and cascade reactions of nitroaromatics by M-UiO-66 metal organic frameworks

The use of metal organic frameworks (MOFs) as photocatalysts is a promising and growing area of research. Given the diverse architectures, linkers, and metals, it is important to understand their effects on catalysis. Herein we compare six MOFs of the UiO-66 family towards photocatalytic reduction of nitro-aromatics to anilines. These MOFs differ in metal identity (Hf, Zr) and linker, and hence this systematic study provides insights to developing next generation MOFs. We found that Hf-based MOFs are superior to the more commonly studied Zr-analogues. Moreover, the linker identity also impact the photocatalysis, with pyridine-based linkers out-performing aniline based linkers and those that lack an embedded basic site. The MOFs studied have unique selectivities for the photoreduction and also allow for the one-pot synthesis of imines from aromatic aldehydes and nitro-aromatics.

CO2-Catalyzed Efficient Dehydrogenation of Amines with Detailed Mechanistic and Kinetic Studies

CO2-catalyzed dehydrogenation of amines has been achieved under photocatalytic conditions. With this concept, various amines have been selectively dehydrogenated to the corresponding imines in the presence of different functional groups such as nitrile, nitro, ester, halogen, ether, thioether, and carbonyl or carboxylic acid moieties. At the end, the CO2-catalyzed synthesis of pharmaceutical drugs has been achieved. The CO2 radical has been detected by EPR spectroscopy using DMPO, and the mechanism of this reaction is proposed on the basis of DFT calculations and experimental evidence.

Preparation method for imine compounds

The invention relates to a preparation method for imine compounds. The preparation method comprises the following concrete steps: with toluene or derivatives thereof and aminated compounds as reaction substrates, adding an oxygen source under the action of a catalyst; putting the above-mentioned substances into a pressure container, enclosing the pressure container and carrying out a stirring reaction at 50 to 150 DEG C for 6 to 24 h; and carrying out oxidative condensation so as to prepare the imine compounds. The method is characterized in that a metal oxide is used as the catalyst. According to the method, raw materials are cheap and easily available; the prepared imine compounds are easily separable from the catalyst; the catalyst can be cyclically used; reaction process is simple, controllable and easy to operate; and the yield of the imine compounds is as high as 90%.

Synthesis of optically pure vic-sulfanyl amines mediated by a remote sulfinyl group

Enantiomerically pure syn-1,2-diaryl-1,2-sulfanylamine derivatives can be obtained in a completely stereoselective manner by reaction of the benzylcarbanion Li-(S)-1 with N-phenyl (or PMP)-arylidene aldimines and further desulfinylation with t-BuLi. Theoretical studies at the DFT (mPW1PW91) level with the CPCM model, by using the Gaussian09 program, provide a good explanation for the stereochemical results.

Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions

Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of (het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Br?nsted acid.