92645-93-7

Upstream product

• 62-53-3 aniline 
• 122-00-9 para-methylacetophenone 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 114200-12-3 1-(p-methylphenyl)ethyl p-nitrobenzenesulfonate 
• 114200-11-2 1-(p-methylphenyl)ethyl p-chlorobenzenesulfonate 
• 82925-34-6 1-(4-methylphenyl)ethyl 4-methylbenzenesulfonate 
• 114200-10-1 1-(p-methylphenyl)ethyl benzenesulfonate 
• 4209-16-9 N-phenyl-1-(p-tolyl)ethan-1-imine 
• 1157634-93-9 1-phenyl-1-(p-tolyl)ethan-1-amine 
• 86767-25-1 1-phenyl-1-(4-methylphenyl)ethanol 
• 76154-06-8 N-phenyl-(1-(4-methylphenyl)ethylidene)amine 
• 766-97-2 4-n-methylphenylacetylene 
• 671-14-7 N-(1-(4-fluorophenyl)ethylidene)aniline 

Downstream Products

• 4209-16-9 N-phenyl-1-(p-tolyl)ethan-1-imine 

Relevant academic research and scientific papers

Internal acidity scale and reactivity evaluation of chiral phosphoric acids with different 3,3′-substituents in Br?nsted acid catalysis

The concept of hydrogen bonding for enhancing substrate binding and controlling selectivity and reactivity is central in catalysis. However, the properties of these key hydrogen bonds and their catalyst-dependent variations are extremely difficult to dete

Iodine-mediated 1,2-aryl migration of primary benzhydryl amines

An iodine-mediated 1,2-aryl migration reaction of primary benzhydryl amines under transition metal-free conditions has been achieved. The crude imines generated by this rearrangement reaction can be directly transformed into various aromatic secondary ami

Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride

A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.

Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones

Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.

Lithium bromide: an inexpensive and efficient catalyst for imine hydroboration with pinacolborane at room temperature

An efficient protocol for the hydroboration of imines is reported. Lithium halide salts are effective catalysts to convert aldimines and ketimines to their corresponding amines. Here, we report excellent isolated yield of secondary amines (>95%) using 3 mol% lithium bromide in THF at room temperature. In addition, DFT calculations for a plausible reaction pathway are reported.

Atomic Pt-Catalyzed Heterogeneous Anti-Markovnikov C-N Formation: Pt10Activating N-H for Pt1δ+-Activated C-C Attack

C-N formation is of great significance to synthetic chemistry, as N-containing products are widely used in chemistry, medicine, and biology. Addition of an amine to an unsaturated carbon-carbon bond is a simple yet effective route to produce new C-N bonds. But how to effectively conduct an anti-Markovnikov addition with high selectivity has been a great challenge. Here, we proposed a strategy for highly regioselective C-N addition via hydroamination by using supported Pt. It has been identified that atomic-scale Pt is the active site for C-N addition with Pt12+ for Markovnikov C-N formation and atomic Pt (Pt1δ+ and Pt10) contributing to anti-Markovnikov C-N formation. A selectivity of up to 92% to the anti-Markovnikov product has been achieved with atomic Pt in the addition of styrene and pyrrolidine. A cooperating catalysis for the anti-Markovnikov C-N formation between Pt1δ+ and Pt10 has been revealed. The reaction mechanism has been studied by EPR spectra and in situ FT-IR spectra of adsorption/desorption of styrene and/or pyrrolidine. It has been demonstrated that Pt10 activates amine to be electrophilic, while Pt1δ+ activates C-C by π-bonding to make β-C nucleophilic. The attack of nucleophilic β-C to electrophilic amine affords the anti-Markovnikov addition. This strategy proves highly effective to a variety of substrates in anti-Markovnikov C-N formation, including aromatic/aliphatic amines reacting with aromatic olefins, aromatic/aliphatic olefins with aromatic amines, and linear aliphatic olefins with secondary aliphatic amines. It is believed that the results provide evidence for the function of varied chemical states in monatomic catalysis.

Development of [3]ferrocenophane-derived N/B frustrated Lewis pairs for the metal-free catalytic hydrogenation of imines

A series of novel [3]ferrocenophane-derived N/B frustrated Lewis pairs (FLPs) were synthesized and successfully applied to the catalytic hydrogenation of imines in 71–93% yields. This approach could be easily conducted on gram scale and provided versatile synthetic route for the key intermediate of sertraline hydrochloride without heavy metal residues.

Synthesis and application of axially chiral biscarbolines with functional N-O and sulfone for 1,2-transfer hydrogenations of ketimines

A series of axially chiral biscarboline-based sulfones were synthesized from L-tryptophane and applied for enantioselective 1,2-transfer hydrogenations of ketimines using trichlorosilane. The catalyst 4e, which had a tertiary butyl group, exhibited a good conversion and high enantioselectivities up to 96%ee in the series of reactions.

Catalyst-Free and Solvent-Free Facile Hydroboration of Imines

A facile process for the catalyst-free and solvent-free hydroboration of aromatic as well as heteroaromatic imines is reported. This atom-economic methodology is scalable, compatible with sterically and electronically diverse imines, displaying excellent tolerance towards various functional groups, and works efficiently at ambient temperature in most of the cases, affording secondary amines in good to excellent yield after hydrolysis.

N,N-coordination Rh complex as well as synthesis method and application thereof

The invention belongs to the technical field of synthesis of organic metal compounds and particularly relates to an N,N-coordination Rh complex as well as a synthesis method and an application thereof. Firstly, a ligand is synthesized from methyl 1H-pyrrole-2-carboxylate as an initial raw material and further reacts with Rh(COD)2Cl, and a metal complex with Rh as a central atom is obtained. The synthesis method is simple, the complex as a catalyst can be used for catalyzing a series of reductive amination reactions of derivatives of acetophenone and aniline, and the product yield is good and is 90% or above.