1738-99-4

Upstream product

• 953-21-9 N-phenylcinnamaldimine 
• 37056-75-0 cinnamaldehyde-(N-phenyl oxime ) 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 62-53-3 aniline 
• 172027-15-5 Phenyl-[3-phenyl-prop-(E)-ylidene]-amine 
• 64-17-5 ethanol 
• 3271-81-6 hydrocinnamanilide 
• 104-53-0 3-phenyl-propionaldehyde 
• 98-95-3 nitrobenzene 
• 100-61-8 N-methylaniline 
• 104-54-1 3-Phenylpropenol 
• 122-97-4 3-Phenyl-1-propanol 
• 953-21-9 N-(3-phenylallylidene)benzenamine 

Downstream Products

• 345224-80-8 N-(3-phenylpropyl)cyclohexanamine 

Relevant academic research and scientific papers

An improved protocol for the selective hydroaminomethylation of arylethylenes

The hydroaminomethylation of arylethylenes with anilines proceeds under mild conditions in the presence of [Rh(cod)2BF4] and dppf as catalyst system to give the corresponding branched amphetamine derivatives in good selectivity and y

A Sustainable Palladium-Intercalated Montmorillonite Clay Catalytic System for Imine Hydrogenation under Mild Conditions

A series of palladium nanoparticles (Pd NPs) intercalated montmorillonite clay catalysts is reported for hydrogenation of 3-diphenyl prop-2-en-1-imine under mild reaction conditions. Pd/clay catalyst was prepared by a simple wet-impregnation method, and t

Reaction of (1-azabuta-1,3-diene)tricarbonyliron(0) complexes with sodium borohydride under microwave conditions

Reaction of (1-azabuta-1,3-diene)tricarbonyliron(0) complexes with sodium borohydride under microwave irradiation leads to formation of saturated secondary amines. When sodium borodeuteride is used for the reaction the products are 1,2,3-trideutero second

Heterogeneous Ru/TiO2for hydroaminomethylation of olefins: multicomponent synthesis of amines

Synthesizing aminesviathe hydroaminomethylation (HAM) reaction of olefins, a multicomponent reaction, has been regarded as one of the most attractive methods compared with the traditional methods considering the atom economy and environmental friendliness. However, the use of homogeneous catalysts, complex ligands containing diphosphine or nitrogen, and base or acid additives has severely hampered the utilization of these methods. Herein, an efficient heterogeneous Ru/TiO2-catalyzed HAM reaction of olefins is developed without any additives. Various amines, including secondary and tertiary amines, can be successfully obtained from olefins including aromatic and aliphatic olefins. Systematic studies demonstrate the lower electron density of Ruδ+and the higher number of acid sites of Ru/TiO2, leading to the high HAM reaction activity of olefins. Most importantly, nitrobenzene derivatives can also be transformed to the corresponding products over Ru/TiO2in excellent yields.

Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols

A series of air-stable N-heterocyclic carbene (NHC) Ir(III) complexes (Ir1-6), bearing various combinations of chlorine, pyridine and NHC ligands, were assayed for the N-alkylation of amines with alcohols. It was found that Ir3, with two monodentate 1,3-bis-methyl-imidazolylidene (IMe) ligands, emerged as the most active complex. A large variety of amines and primary alcohols were efficiently converted into mono-N-alkylated amines in 53–96% yields. As a special highlight, for the challenging MeOH, selective N-monomethylation could be achieved using KOH as a base under an air atmosphere. Moreover, this catalytic system was successfully applied to the gram-scale synthesis of some valuable compounds.

Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols

Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.

Tungsten-Catalyzed Direct N-Alkylation of Anilines with Alcohols

The implementation of non-noble metals mediated chemistry is a major goal in homogeneous catalysis. Borrowing hydrogen/hydrogen autotransfer (BH/HA) reaction, as a straightforward and sustainable synthetic method, has attracted considerable attention in the development of non-noble metal catalysts. Herein, we report a tungsten-catalyzed N-alkylation reaction of anilines with primary alcohols via BH/HA. This phosphine-free W(phen)(CO)4 (phen=1,10-phenthroline) system was demonstrated as a practical and easily accessible in-situ catalysis for a broad range of amines and alcohols (up to 49 examples, including 16 previously undisclosed products). Notably, this tungsten system can tolerate numerous functional groups, especially the challenging substrates with sterically hindered substituents, or heteroatoms. Mechanistic insights based on experimental and computational studies are also provided.

Ureate Titanium Catalysts for Hydroaminoalkylation: Using Ligand Design to Increase Reactivity and Utility

Hydroaminoalkylation describes the atom-economical catalytic synthesis of amines by forming new Csp3-Csp3 bonds using readily available amine and alkene feedstocks. Herein, we describe an earth-abundant and cost-efficient titanium catalyst generated in si

Direct, Catalytic α-Alkylation of N-Heterocycles by Hydroaminoalkylation: Substrate Effects for Regiodivergent Product Formation

Saturated N-heterocycles are prevalent in pharmaceutical and agrochemical industries, yet remain challenging to catalytically alkylate. Most strategies for C-H activation of these challenging substrates use protected amines or high loadings of precious me

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.