22643-14-7

Upstream product

• 111-83-1 1-bromo-octane 
• 108-91-8 cyclohexylamine 
• 20667-16-7 N,N-dicyclopentylamine 
• 89231-76-5 N-chloro-1-octylamine 
• 124-13-0 Octanal 
• 1217269-17-4 N-cyclohexyl-N-octylmethanesulfonamide 
• 111-86-4 n-Octylamine 
• 108-94-1 cyclohexanone 
• 108-93-0 cyclohexanol 
• 108-95-2 phenol 
• 101-84-8 diphenylether 
• 98-95-3 nitrobenzene 
• 100-61-8 N-methylaniline 
• 62-53-3 aniline 

Downstream Products

• 101-81-5 Diphenylmethane 
• 110426-41-0 C₁₄H₂₈N^(1-)*Li⁽¹⁺⁾ 
• 110426-47-6 C₁₄H₂₈N^(1-)*K⁽¹⁺⁾ 
• 108-88-3 toluene 

Relevant academic research and scientific papers

Highly Selective Reductive Cross-Amination between Aniline or Nitroarene Derivatives and Alkylamines Catalyzed by Polysilane-Immobilized Rh/Pt Bimetallic Nanoparticles

Reductive cross-amination between imine intermediates generated through partial hydrogenation of aniline or nitroarene derivatives and alkylamines is an ideal method for obtaining N-alkylated cyclohexylamine derivatives; however, no such transformations have hitherto been established. Here, we report a highly selective reductive cross-amination using aniline derivatives and alkylamines catalyzed by heterogeneous Rh/Pt bimetallic nanoparticles under mild conditions. The catalyst was recovered and reused for five runs, keeping high activity. In this reaction, imine intermediates generated during the course of partial hydrogenation of aniline derivatives were trapped immediately by strongly interacting primary alkylamines with the catalyst, which caused a highly selective transformation to give the desired products, while suppressing dicyclohexylamine formation.

Rh-PVP Catalyzed Reductive Amination of Phenols by Ammonia or Amines to Cyclohexylamines under Solvent-free Conditions

Colloidal metal nanoparticles were examined for reductive amination of phenol by ammonia under mild reaction conditions. The results showed that Rh-PVP was the most active catalyst for reductive amination reaction. Linear, cyclic, and amino alcohols were used as nucleophiles and converted to primary/secondary/tertiary amines. Using this strategy, the synthesis of an industrially important chemical, N-cyclohexyl- 2-pyrrolidone was explored.

High-Throughput Screening of Reductive Amination Reactions Using Desorption Electrospray Ionization Mass Spectrometry

This study describes the latest generation of a high-throughput screening system that is capable of screening thousands of organic reactions in a single day. This system combines a liquid handling robot with desorption electrospray ionization (DESI) mass spectrometry (MS) for a rapid reaction mixture preparation, accelerated synthesis, and automated MS analysis. A total of 3840 unique reductive amination reactions were screened to demonstrate the throughputs that are capable with the system. Products, byproducts, and intermediates were all monitored in full-scan mass spectra, generating a complete view of the reaction progress. Tandem mass spectrometry experiments were conducted to verify the identity of the products formed. The amine and electrophile reactivity trends represented in the data match what is expected from theory, indicating that the system accurately models the reaction performance. The DESI results correlated well with those generated using more traditional mass spectrometry techniques like liquid chromatography-mass spectrometry, validating the data generated by the system.

Ni-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines

Phenol and its derivatives, which naturally occur in lignocellulose, can be considered as a renewable feedstock not only for aromatic, but also for alicyclic compounds, such as primary and N-substituted cyclohexylamines. So far, the latter are mostly produced from non-renewable starting materials like benzene via problematic nitration/reduction or cross-coupling routes. Herein, an efficient reductive amination of phenol with ammonia or amines is demonstrated, for the first time without the need for rare and expensive noble metals and without using any additives. Various supported Ni catalysts were screened and we elucidated the influence of the key parameters, including the acid-base properties of the supporting material. Acquired knowledge was then applied to different phenol-ammonia/amine combinations, resulting in the synthesis of various primary, secondary and tertiary cyclohexylamines in fair to very high yields.

Synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compound

The invention discloses a synthesis method for converting lignin 4-O-5 model compound diaryl ether into a nitrogen-containing compound. According to the synthesis method, a diaryl ether compound andan amine compound are subjected to a heating reaction in a certain amount of a solvent (containing a certain amount of water) in an argon atmosphere (containing a certain amount of air) under the actions of a metal catalyst and sodium borohydride, such that the drug with the important physiological activity or the compound with the natural product skeleton containing nitrogen is formed by directlycoupling the C-O bond cut and the amine compound cross while the corresponding aromatic hydrocarbon is obtained. According to the present invention, the synthesis method has characteristics of simpleand easily-available raw materials, high conversion rate, important product and good yield, and has broad application prospects in the degradation and deep development and utilization of lignin.

Palladium-Catalyzed Formal Cross-Coupling of Diaryl Ethers with Amines: Slicing the 4-O-5 Linkage in Lignin Models

Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (α-O-4, β-O-4, and 4-O-5 linkages) and other C?C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)?O bond cleavages form valuable nitrogen-containing derivatives.

Selective Activation of Alcohols in the Presence of Reactive Amines over Intermetallic PdZn: Efficient Catalysis for Alcohol-Based N-Alkylation of Various Amines

Pd-based intermetallic compounds supported on Al2O3 (PdxMy/Al2O3, where M = Bi, Cu, Fe, Ga, In, Pb, Sn, or Zn) were prepared and tested as catalysts for the selective activation of alcohols in the presence of reactive amines, which is highly challenging and is the key strategy for alcohol-based N-alkylation of amines. Although the Pd/Al2O3 catalyst exhibited a high catalytic activity, undesired side reactions such as amine dimerization (via amine activation) and C-O bond scission occurred, resulting in a poor yield of the N-alkylation product. In contrast, the PdZn/Al2O3 catalyst acted as an efficient catalyst for this reaction, displaying high catalytic activities, selectivities, and atom efficiencies and a wide substrate scope. Detailed kinetic and computational studies revealed that the relative affinity of Pd for alcohol and amine drastically changes by the formation of a PdZn intermetallic phase. On monometallic Pd, the adsorption and activation of amines are preferred over those of alcohols in terms of thermodynamic and kinetic aspects, respectively. However, this trend is inverted on PdZn, allowing preferential adsorption and activation of alcohols and, hence, selective N-alkylation.

An efficient heterogenized palladium catalyst for N-alkylation of amines and α-alkylation of ketones using alcohols

A silica supported palladium-NiXantphos complex is reported as an efficient and a high turnover heterogeneous catalyst for the N-alkylation of amines and the α-alkylation of ketones using readily available alcohols under neat conditions at 120-140 °C following hydrogen borrowing strategy. The catalyst is easily separable and offers negligible amount of palladium leaching (0.01 ppm). A high turnover number of about 46000 for the N-alkylation of amines and 4400 for the α-alkylation of ketones were achieved in the respective single batch reactions. The catalyst is recyclable up to four times without appreciable change in catalytic performance.

Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines

Phenols, being readily available from naturally abundant lignins, are important future feedstocks for the renewable production of fuels, chemicals, and energy. Herein, a highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using cheap and safe sodium formate as hydrogen donor is described. A variety of secondary and tertiary substituted cyclohexylamines can be synthesized under convenient conditions in moderate to excellent yields.

PROCESS FOR PREPARING AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION IN THE PRESENCE OF A COMPLEX CATALYST COMPRISING IRIDIUM AND AN AMINO ACID

The invention relates to a process for preparing amines (A) by alcohol amination of alcohols (Al) by means of an aminating agent (Am) with elimination of water, wherein the alcohol amination is carried out in the presence of a complex catalyst comprising iridium and an amino acid.