476148-85-3

Upstream product

• 108-91-8 cyclohexylamine 
• 536-74-3 phenylacetylene 
• 823-76-7 Cyclohexyl methyl ketone 
• 62-53-3 aniline 

Downstream Products

• 58008-17-6 N-phenyl-1-cyclohexylethylamine 

Relevant academic research and scientific papers

Highly efficient and selective photocatalytic hydroamination of alkynes by supported gold nanoparticles using visible light at ambient temperature

The direct hydroamination of alkynes driven by visible light can be achieved in high yield and selectivity at ambient temperature using supported gold nanoparticles (AuNPs) as photocatalysts. Aniline molecules interact with visible light activated AuNPs m

Development of highly enantioselective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile

l-Pipecolinic acid derived N-formamides have been developed as new Lewis basic organocatalysts that promote the asymmetric reduction of N-aryl ketimines using trichlorosilane as the reducing agent. The substituent on N4 of the piperazinyl backbone and the

Rationally-designed S-chiral bissulfinamides as highly enantioselective organocatalysts for reduction of ketimines

We recently reported the first example of S-chiral organocatalysts, that are highly efficient and enantioselective in substoichometric amounts, and which use a chiral monosulfinamide group as Lewis base to activate trichlorosilane (HSiCl3) to reduce N-arylketimines. Aplausible mechanism involving two molecules of the monosulfinamde catalyst for the activation of HSiCl 3 prompted us to design S-chiral bissulfinamides as new catalysts. We herein describe our findings that an easily prepared S-chiral bissulfinamide bearing a five-methylene linkage not only inherited the excellent substrate generality from the monosulfinamide catalysts, but also exhibited further improved enantioselectivity.

Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane

Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by a new N-methyl L-valine derived Lewis basic organocatalyst, such as 4d, with high enantioselectivity. The structure-reactivity investigation suggests hydrogen bonding and arene-arene interactions between the catalyst and the incoming imine as the main factor determining the enantiofacial selectivity.

Ruthenium-catalyzed transfer hydrogenation of imines by propan-2-ol in benzene

Transfer hydrogenation of a variety of different imines to the corresponding amines by propan-2-ol in benzene catalyzed by [Ru2(CO)4(μ H)(C4Ph4COHOCC4Ph4)] (1) has been studied. The reaction is highly efficient with turnover frequencies of over 800 per hour, and the product amines were obtained in excellent yields. A remarkable concentration dependence of propan-2-ol was observed when the reaction was run in benzene as cosolvent. An optimum was obtained at 24 equivalents of propan-2-ol to imine, and further increase of the propan-2-ol led to a dramatic decrease in rate. Also the use of polar cosolvents with 24 equivalents of propan-2-ol gave a low rate. It was found that ketimines react faster than aldimines and that electron-donating substituents on the imine increase the rate of the catalytic transfer hydrogenation. Electron-withdrawing substituents decreased the rate. An isomerization was observed with imines having an α-hydrogen at the N-alkyl substituent, which is in accordance with a mechanism involving a ruthenium-amine intermediate. It was demonstrated that the ruthenium-amine complex from α-methylbenzylamine, corresponding to the postulated intermediate, can replace 1 as catalyst in the transfer hydrogenation of imines. A primary deuterium isotope effect of kCH/CD = 2.7 ± 0.25 was observed when 2-deuterio-propan-2-ol vas used in place of propan-2-ol in the ransfer hydrogenation of N-phenyl-(1-phenylethylidene)amine.

A method for the asymmetric hydrosilylation of N-aryl imines

graph presented The asymmetric reduction of N-aryl imines to yield chiral amines with enantiomeric excesses above 90% was achieved. Ethylenebis(η5-tetrahydroindenyl)titanium difluoride ((EBTHI)TiF2,1) was employed as the precatalyst