345224-80-8

Upstream product

• 91-22-5 quinoline 
• 857780-56-4 2-cyclohexylamino-4-phenyl-butyric acid 
• 15286-54-1 N-(3-phenylallylidene)cyclohexanamine 
• 64-19-7 acetic acid 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 108-91-8 cyclohexylamine 
• 626-62-0 Cyclohexyl iodide 
• 2038-57-5 3-Phenylpropan-1-amine 
• 62-53-3 aniline 
• 104-53-0 3-phenyl-propionaldehyde 
• 1738-99-4 N-(3-phenylpropyl)aniline 
• 100-60-7 N-methylcyclohexylamine 
• 122-97-4 3-Phenyl-1-propanol 

Downstream Products

• 1438886-23-7 N-cyclohexyl-N-(3-phenylpropyl)-4-methylbenzenesulfonamide 
• 104-53-0 3-phenyl-propionaldehyde 

Relevant academic research and scientific papers

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

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.

Polysilane-Immobilized Rh-Pt Bimetallic Nanoparticles as Powerful Arene Hydrogenation Catalysts: Synthesis, Reactions under Batch and Flow Conditions and Reaction Mechanism

Hydrogenation of arenes is an important reaction not only for hydrogen storage and transport but also for the synthesis of functional molecules such as pharmaceuticals and biologically active compounds. Here, we describe the development of heterogeneous Rh-Pt bimetallic nanoparticle catalysts for the hydrogenation of arenes with inexpensive polysilane as support. The catalysts could be used in both batch and continuous-flow systems with high performance under mild conditions and showed wide substrate generality. In the continuous-flow system, the product could be obtained by simply passing the substrate and 1 atm H2 through a column packed with the catalyst. Remarkably, much higher catalytic performance was observed in the flow system than in the batch system, and extremely strong durability under continuous-flow conditions was demonstrated (>50 days continuous run; turnover number >3.4 × 105). Furthermore, details of the reaction mechanisms and the origin of different kinetics in batch and flow were studied, and the obtained knowledge was applied to develop completely selective arene hydrogenation of compounds containing two aromatic rings toward the synthesis of an active pharmaceutical ingredient.

Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light

Although the alkylation of an amine by an alkyl halide serves as a textbook example of a nucleophilic substitution reaction, the selective mono-alkylation of aliphatic amines by unactivated, hindered halides persists as a largely unsolved challenge in organic synthesis. We report herein that primary aliphatic amines can be cleanly mono-alkylated by unactivated secondary alkyl iodides in the presence of visible light and a copper catalyst. The method operates under mild conditions (-10 °C), displays good functional-group compatibility, and employs commercially available catalyst components. A trapping experiment with TEMPO is consistent with C-N bond formation via an alkyl radical in an out-of-cage process.

Ruthenium-catalyzed N-alkylation of amines with alcohols under mild conditions using the borrowing hydrogen methodology

Using a simple amino amide ligand, ruthenium-catalyzed one-pot alkylation of primary and secondary amines with simple alcohols was carried out under a wide range of conditions. Using the alcohol as solvent, alkylation was achieved under mild conditions, even as low as room temperature. Reactions occurred with high conversion and selectivity in many cases. Reactions can also be carried out at high temperatures in organic solvent with high selectivity using stoichiometric amounts of the alcohol.

A 2,6-bis(phenylamino)pyridinato titanium catalyst for the highly regioselective hydroaminoalkylation of styrenes and 1,3-butadienes

The C-C bond forming catalytic hydroaminoalkylation of terminal alkenes, 1,3-dienes, or styrenes allows a direct and highly atom efficient (100 %) synthesis of amines which can result in the formation of two regioisomers, the linear and the branched product. We present a new titanium catalyst with 2,6-bis(phenylamino)pyridinato ligands for intermolecular hydroaminoalkylation reactions of styrenes and 1-phenyl-1,3-butadienes that delivers the corresponding linear hydroaminoalkylation products with excellent regioselectivities. Linear progress: A new Ti complex with 2,6-bis(phenylamino) pyridinato ligands catalyzes highly regioselective hydroaminoalkylation reactions of styrenes. The process that directly gives access to the corresponding linear hydroaminoalkylation products offers a new and flexible synthetic approach towards pharmaceutically important 3-arylpropylamines. It is also possible to convert (E)-1-phenyl-1,3-butadienes into the corresponding linear products.

A convenient and general reduction of amides to amines with low-valent titanium

Low-valent titanium readily prepared in situ from TiCl4 and Mg powder in THF is found to be an active agent for the reduction of amides which were previously considered to be inert towards low-valent titanium. The reaction proceeds under very mild conditions, and is applicable to all types of amides, primary, secondary and tertiary, to produce the corresponding amines in good to excellent yields. This new finding provides a practical, convenient and general method for the important transformation of amides to amines. A plausible reaction mechanism is proposed.

A simple protocol for direct reductive amination of aldehydes and ketones using potassium formate and catalytic palladium acetate

A method for direct reductive amination of aldehydes and ketones, including α,β-unsaturated carbonyl compounds, has been developed, which requires potassium formate as reductant and palladium acetate as catalyst. Suitable amines include both primary and secondary aliphatic and aromatic amines.

Oxidative deamination of various primary amines to the corresponding carbonyl compounds by using N-tert-butylphenylsulfinimidoyl chloride

Various linear and non-linear primary amines were oxidatively deaminated to afford the corresponding carbonyl compounds in good to excellent yields by the following procedure: (i) initial formation of their N-cyclohexylated or N-mesylated derivatives, (ii) subsequent oxidation of these derivatives by using N-tert-butylphenylsulfinimidoyl chloride (1) and DBU, (iii) one-pot acid-hydrolysis of thus formed imines to carbonyl compounds.

Zwitterionic rhodium complex catalyzed hydroaminomethylation of arylethylenes

The hydroaminomethylation of arylethylenes can be achieved in high regioselectivity using the zwitterionic rhodium complex [Rh+(cod)(η6-PhBPh3)-] (1) as the catalyst under relatively mild conditions.