16035-83-9

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 106-49-0 p-toluidine 
• 64-17-5 ethanol 
• 4450-68-4 4-nitrobenzyl tosylate 
• 100-42-5 styrene 
• 33442-37-4 N-(4-nitrobenzylidene)-4-methylaniline 
• 555-16-8 4-nitrobenzaldehdye 
• 845777-08-4 2-(1,3-dithian-2-ylidene)but-3-ynoic acid 
• 730-39-2 N-(4-nitrobenzylidene)-4-methylaniline 

Downstream Products

• 118072-35-8 3-(2-Dimethylaminomethyl-4-methyl-phenylamino)-propionitrile 
• 555-16-8 4-nitrobenzaldehdye 
• 6421-27-8 bis-[4-(p-tolylimino-methyl)-phenyl]-diazene-N-oxide 
• 723293-39-8 4-methyl-2,6,N-trinitro-N-(4-nitro-benzyl)-aniline 
• 4389-35-9 N-(4-amino-benzylidene)-p-toluidine 
• 127598-76-9 N-(2-cyanoethyl) N-(4-nitrobenzyl)-4-methylaniline 

Relevant academic research and scientific papers

Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds

A strategy based on the cooperation between metal and bonded cofactor mimics was applied to the transfer hydrogenation of CN bonds. We designed and synthesized a rhodium complex containing a 1,3-dimethylbenzoimidazole moiety, which could transfer hydride from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations and isotope experiments, a plausible mechanism for this biomimetic reduction of CN bonds were proposed.

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.

Imidazolium-based ionic liquid-catalyzed hydrosilylation of imines and reductive amination of aldehydes using hydrosilane as the reductant

The first imidazolium-based ionic liquid-catalyzed hydrosilylation of imine and reductive amination of aldehydes with primary amines using a catalytic amount of 1-butyl-3-methylimidazolium tetrachloride iron [BMIm][FeCl4] and Ph2SiH2 as a reductant were performed under mild conditions. Good yields of secondary amines with high chemoselectivity and a tolerance for a wide range of functional groups were obtained.

Efficient Ruthenium(II)-Catalyzed Direct Reductive Amination of Aldehydes under Mild Conditions Using Hydrosilane as the Reductant

A direct reductive amination of aldehydes with anilines is performed with a ruthenium(II)-(arene) catalyst. The [RuCl2(p-cymene)]2/Ph2SiH2 catalytic system is very efficient for the synthesis of secondary amines and tertiary amines in good yields, and is highly chemoselective, tolerating a wide range of functional groups, such as NO2, CN, CO2Me, F, Cl, Br, OMe, Me, furyl and alkyl. We also report an interesting direductive amination of 2-ethylbutanal.

A Highly Efficient Base-Metal Catalyst: Chemoselective Reduction of Imines to Amines Using An Abnormal-NHC-Fe(0) Complex

A base-metal, Fe(0)-catalyzed hydrosilylation of imines to obtain amines is reported here which outperforms its noble-metal congeners with the highest TON of 17000. The catalyst, (aNHC)Fe(CO)4, works under very mild conditions, with extremely low catalyst loading (down to 0.005 mol %), and exhibits excellent chemoselectivity. The facile nature of the imine reduction under mild conditions has been further demonstrated by reducing imines towards expensive commercial amines and biologically important N-alkylated sugars, which are difficult to achieve otherwise. A mechanistic pathway and the source of chemoselectivity for imine hydrosilylation have been proposed on the basis of the well-defined catalyst and isolable intermediates along the catalytic cycle.

Halogen-bonding-induced hydrogen transfer to C=N bond with hantzsch ester

Several bidentate dihydroimidazolines were prepared and investigated as catalysts for hydrogen transfer reduction of C=N bond with Hantzsch ester. Highly efficient reactions were observed for quinolines and imines with low catalyst loading of 2 mol %. The presence of halogen bonding was elucidated using NMR studies and isothermal calorimeric titrations. Binding constants of the XB donors were also measured using isothermal calorimeric titrations (ITC).

Bio-inspired catalytic imine reduction by rhodium complexes with tethered hantzsch pyridinium groups: Evidence for direct hydride transfer from dihydropyridine to metal-activated substrate

Inspired by Nature: A conceptually new design for a catalyst, combining a metal center abutted to an organic hydride donor, is demonstrated for the formate-driven transfer hydrogenation of imines under ambient conditions. A key step, transfer of hydride from the organohydride donor to the metal-polarized substrate, mirrors that in metallo-(de)hydrogenase enzymes.

Amine synthesis through mild catalytic hydrosilylation of imines using polymethylhydroxysiloxane and [RuCl2(arene)]2 catalysts

Tolerate silicone! The stable [RuCl2(p-cymene]2 complex is an efficient catalyst for the direct chemoselective hydrosilylation of functionalized aldimines and ketimines into amines, using polymethylhydroxysiloxane as an inexpensive, stable, and safe hydrosilane source. The catalysis operates in ethanol, under air at room temperature, and tolerates the ketone ester and alkene functionality. Copyright

Ethynyl ketene-S,S-acetals: The highly reactive electron-rich dienophiles and applications in the synthesis of 4-functionalized quinolines via a one-pot three-component reaction

(Chemical Equation Presented) An efficient synthetic method for 4-functionalized quinoline derivatives, 4-((1,3-dithian-2-ylidene)methyl) quinolines, has been developed. Mediated by trifluoromethanesulfonic acid, ethynyl ketene-S,S-acetals can react in a one-pot procedure with various arylamines and aldehydes under mild conditions to give the corresponding quinoline derivatives in good to high yields via a consecutive arylimine formation, regiospecific aza-Diels-Alder (Povarov) reaction, and reductive amination.

Solvent-free mechanochemical and one-pot reductive benzylizations of malononitrile and 4-methylaniline using Hantzsch 1,4-dihydropyridine as the reductantt

The properties of Hantzsch 1,4-dihydropyridine, which possesses excellent reducibility, were investigated. The synthesis of benzyl malononitriles and anilines were also studied. Direct reductive benzylizations of malononitrile and 4-methylaniline by aromatic aldehydes were achieved using a Hantzsch 1,4-dihydropyridine as the reductant. It was observed that there is no need for the separation of the in situ generated benzylidene malononitriles and p-tolylamines.