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Upstream product

• 6749-54-8 1-phenylethyl p-toluenesulfonate 
• 106-47-8 4-chloro-aniline 
• 114200-14-5 1-phenylethyl p-nitrobenzenesulfonate 
• 113694-01-2 1-phenylethyl benzenesulfonate 
• 114200-13-4 1-phenylethyl p-chlorobenzenesulfonate 
• 672-65-1 (1-chloroethyl)benzene 
• 98-86-2 acetophenone 
• 100-42-5 styrene 
• 25287-19-8 N-(1-phenylethylidene)-4-chloroaniline 
• 536-74-3 phenylacetylene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 618-36-0 rac-methylbenzylamine 
• 100-41-4 ethylbenzene 
• 99421-72-4 1-phenylethyl 2,2,2-trichloroacetimidate 

Downstream Products

• 3159-01-1 4-chloro-2-(1-phenylethyl)benzenamine 

Relevant academic research and scientific papers

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

Chan-Lam Amination of Secondary and Tertiary Benzylic Boronic Esters

We report a Chan-Lam coupling reaction of benzylic and allylic boronic esters with primary and secondary anilines to form valuable alkyl amine products. Both secondary and tertiary boronic esters can be used as coupling partners, with mono-alkylation of the aniline occurring selectively. This is a rare example of a transition-metal-mediated transformation of a tertiary alkylboron reagent. Initial investigation into the reaction mechanism suggests that transmetalation from B to Cu occurs through a single-electron, rather than a two-electron process.

Diethylsilane as a Powerful Reagent in Au Nanoparticle-Catalyzed Reductive Transformations

Diethylsilane (Et2SiH2), a simple and readily available dihydrosilane, that exhibits superior reactivity, as compared to monohydrosilanes, in a series of reductive transformations catalyzed by recyclable and reusable Au nanoparticles (1 mol-%) supported on TiO2. It reduces aldehydes or ketones almost instantaneously at ambient conditions. It can be used in a one pot rapid reductive amination procedure, in which premixing of aldehyde and amine is required prior to the addition of the reducing agent and the catalyst, even in a protic solvent. An unprecedented method for the synthesis of N-arylisoindolines is also shown in the reductive amination between o-phthalaldehyde and anilines. In this transformation, it is proposed that the intermediate N,2-diphenylisoindolin-1-imines are reduced stepwise to the isoindolines. Finally, Et2SiH2 readily reduces amides into amines in excellent yields and shorter reaction times relative to previously known analogous nano Au(0)-catalyzed protocols.

In Water Markovnikov Hydration and One-Pot Reductive Hydroamination of Terminal Alkynes under Ruthenium Nanoparticle Catalysis

In the presence of Shvo's catalyst [2,3,4,5-tetraphenyl-1,3-cyclopentadien-1-ol, ruthenium(II) complex], a small quantity of aniline and TGPS-750-M surfactant, terminal alkynes were hydrated under microwave (MW) dielectric heating in water as solvent with high conversion and good yield. The reaction gives the Markovnikov product exclusively, unlike that commonly observed with ruthenium complexes. Under the influence of MWs, Ru nanoparticles embedded in the nanomicelle environment were formed, acting as the effective hydration catalyst. Introducing sodium formate in the aqueous phase and using a stoichiometric amount of amines, the Ru nanoparticle nanomicelle catalyst gave the first example of one-pot single-step hydroamination of alkynes with the formation of the corresponding secondary amines. The reaction is characterized by low environmental impact as TGPS-750-M is required in low amount, and organic solvents employed only for product separation or catalyst recycling.

Iron-catalyzed reductive coupling of nitroarenes with olefins: Intermediate of iron-nitroso complex

Using a single half-sandwich iron(II) compound, CpFe(1,2-Ph2PC6H4S)(NCMe) (Cp- = C5Me5-, 1) as a catalyst, reductive coupling of nitroarenes with olefins has been achieved by a well-defined iron(II)/(EtO)3SiH system. Through either inter- or intramolecular reductive coupling, various branched amines and indole derivatives have been directly synthesized in one-pot. Mechanistic studies showed that the catalysis is initiated by activation of nitroarenes by the iron(II) catalyst with silane, generating iron-nitrosoarene intermediate for the C-N bond coupling.

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.

Visible-Light-Induced Copper-Catalyzed Intermolecular Markovnikov Hydroamination of Alkenes

A visible-light-induced copper-catalyzed intermolecular hydroamination of alkenes using commercially accessible primary and secondary amines has been established. This effective method exhibits good tolerance of a broad range of functional groups and provides a facile access to an array of valuable amines with Markovnikov regioselectivity. The process can be positively expected to be used in bioactive amines, and it may provide new potential in the discovery of copper-catalyzed hydrofunctionalization reactions.

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.

Enhanced Catalytic Activity of Oxygen-Tethered IrIII NHC Complexes in Aqueous Transfer Hydrogenative Reductive Amination Reactions: Experimental Kinetic and Mechanistic Study

The synthesis and characterization of seven new IrIII complexes containing o-phenoxide or o-naphthoxide chelated N-heterocyclic carbene ligands is reported herein. The crystal structures of six of the complexes have been determined. These complexes efficiently catalyze the transfer hydrogenative reductive amination (RA) of carbonyls and amines in water. Amongst the complexes tested, the introduction of o-naphthoxide on a nitrogen atom of imidazole based NHC ligand greatly increased the catalytic activity. The catalytic system has a broad substrate scope, which allows the synthesis of a variety of amines in excellent yields and with high turnover numbers up to 490 (for ketones) and 14800 (for aldehydes). The mechanism of aqueous RA reaction with an o-aryloxide chelated NHC-IrIII catalyst has been investigated by NMR spectroscopy and kinetic measurements. These studies suggest that the transfer hydrogenation (TH) is turnover-limited by the hydride formation step. As a result of the 1H NMR studies, the higher catalytic activity of o-naphthoxide chelated catalyst (3 g) over o-phenoxide chelated one (3 b) can be attributed partly due to the faster formation of an iridium hydride, the key intermediate in the RA reactions.