117555-73-4

Upstream product

• 66-25-1 hexanal 
• 98-95-3 nitrobenzene 
• 821-41-0 5-Hexen-1-ol 
• 62-53-3 aniline 
• 928-94-9 (Z)-2-hexen-1-ol 
• 928-95-0 (E)-2-Hexen-1-ol 
• 111-27-3 hexan-1-ol 
• 693-02-7 hex-1-yne 

Downstream Products

• 30189-89-0 N-methyl-N-hexylaniline 

Relevant academic research and scientific papers

Titanium-Catalyzed Hydroamination and Multicomponent Coupling with a Simple Silica-Supported Catalyst

Hydroamination and multicomponent coupling reactions catalyzed by homogeneous Ti(IV) complexes can produce valuable imines, amines, and other nitrogen-containing organic building blocks. Typically catalysts for this transformation are very sensitive to an

Activated Carbon Supported Ruthenium Nanoparticles Catalyzed Synthesis of Imines from Aerobic Oxidation of Alcohols with Amines

Abstract: Imines were synthesized from the cross-coupling of alcohols with amines catalyzed by activated carbon (AC) supported ruthenium nanoparticles under atmospheric molecular oxygen without aid of any additives. The readily prepared catalyst 5%Ru/AC showed good to excellent (yield > 90%) performances in the reaction of aromatic and heterocyclic alcohols with various amines, such as aromatic, aliphatic and heterocyclic amines. This protocol is simple, efficient, and environmentally friendly, and the catalyst can be easily recovered without major ruthenium loss. Graphical Abstract: Imines were synthesized from the cross-coupling of alcohols with amines catalyzed by activated carbon (AC) supported ruthenium nanoparticles under atmospheric molecular oxygen without aid of any additives. This protocol is simple, efficient, and environment friendly, and the readily prepared catalyst 5%Ru/AC showed good to excellent performances in the reaction of aromatic and heterocyclic alcohols with various amines, such as aromatic, and aliphatic amines. [Figure not available: see fulltext.]

A bifunctional PdVMgO solid catalyst for the one-pot selective N-monoalkylation of amines with alcohols

It has been found that a bifunctional metal Pd/base (MgO) catalyst performs the selective monoalkylation of amines with alcohols. The reaction goes through a series of consecutive steps in a cascade mode that involves: 1) the abstraction of hydrogen from the alcohol that produces the metal hydride and the carbonyl compound; 2) condensation of the carbonyl with the amine to give an imine, and 3) hydrogenation of the imine with the surface hydrogen atoms from the metal hydride. Based on isotopic and spectroscopic studies and on the rate of each elementary step, a global reaction mechanism has been proposed. The controlling step of the process is the hydride transfer from the metal to the imine. By changing the crystallite size of the Pd, it is demonstrated that this is a structure-sensitive reaction, whereas the competing processes that lead to subproducts are not. On these bases, a highly selective catalyst has been obtained with Pd crystallite size below 2.5 nm in diameter. The high efficiency of the catalytic system has allowed us to extend the process to the one-pot synthesis of piperazines.

A general study of [(η5-Cp′)2Ti(η 2-Me3SiC2SiMe3)]-catalyzed hydroamination of terminal alkynes: Regioselective formation of Markovnikov and anti-Markovnikov products and mechanistic explanation (Cp′=C (5)H(5), C(5)H(4)Et, C(5)Me(5))

A general study of the regioselective hydroamination of terminal alkynes in the presence of [(η5-Cp)2Ti(η2-Me 3SiC2SiMe3)] (1), [(η5-CpEt) 2Ti(η2-Me3SiC2SiMe3)] (CpEt= ethylcyclopentadienyl) (2), and [(η5-Cp*) 2Ti(η2-Me3SiC2SiMe3)] (Cp=pentamethylcyclopentadienyl) (3) is presented. While aliphatic amines give mainly the anti-Markovnikov products, anilines and aryl hydrazines yield the Markovnikov isomer as main products. Interestingly, using aliphatic amines such as n-butylamine and benzylamine the different catalysts lead to a significant change in the observed regioselectivity. Here, for the first time a highly selective switch from the Markovnikov to the anti-Markovnikov product is observed simply by changing the catalyst. Detailed theoretical calculations for the reaction of propyne with different substituted anilines and tert-butylamine in the presence of [(η5-C5H5)Ti(= NR)(NHR)] (R=4-C6H4X; X=H, F, Cl, CH3, 2,6-dimethylphenyl) reveal that the experimentally observed regioselectivity is determined by the relative stability of the corresponding π-complexes 10. While electrostatic stabilization favors the Markovnikov performance for aniline, the steric repulsive destabilization disfavors the Markovnikov performance for tert-butylamine.

Anti-Markovnikov hydroamination of terminal alkynes

Titanocene-η-alkyne complexes such as 1 are efficient catalysts for the hydro-amination of terminal alkynes to imines (see scheme; R = alkyl, R′ = SiMe3 or Ph). Excellent yields of imines and good to excellent regioselectivities for the anti-Markovnikov products were obtained.

SYNTHESIS OF ALIPHATIC-AROMATIC AMINES IN THE PRESENCE OF THE COMPLEXES OF PALLADIUM IONS WITH POLYTRIMETHYLOLMELAMINE

The complexes of palladium ions with polytrimethylolmelamine effectively catalyze the hydrogenation amination of aldehydes with nitrobenzene under mild conditions (1 atm of hydrogen, 18-50 deg C).The intermediate products in the amination of aldehydes with nitro-, azo-, and azoxybenzene are phenylhydroxylamine, aniline, and the corresponding azomethine.