7476-71-3

Upstream product

• 100-42-5 styrene 
• 142-04-1 aniline hydrochloride 
• 62-53-3 aniline 
• 779-54-4 phenyl(1-phenylethyl)amine 
• 1520-21-4 4-vinyl benzylamine 
• 71-43-2 benzene 
• 98-85-1 1-Phenylethanol 
• 103-63-9 1-phenyl-2-bromoethane 
• 106-40-1 4-bromo-aniline 
• 4426-21-5 oxybis(diphenylborane) 
• 123077-39-4 N'-(1-(4-aminophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 
• 76716-27-3 N-(α-Phenethyl)-aniline hydrochloride 

Downstream Products

• 7476-72-4 N-(4-(1-phenylethyl)phenyl)acetamide 

Relevant academic research and scientific papers

Zeolite catalyzed hydroarylation of alkenes with aromatic amines under organic ligand-free conditions

The hydroarylation of alkenes with aromatic amines is recognized as the most atom-economical and straightforward approach to obtain functional aromatic amines, which are versatile building blocks in organic synthesis and material chemistry. However, controllable synthesis of single hydroarylation product is still a significant challenge because hydroarylation reaction often delivers four hydroarylation products and hydroamination products are also produced during the reaction. Herein, we report the first example of heterogeneous zeolite catalyzed hydroarylation of styrene and norbornene with aniline derivatives under organic ligand-free conditions. With the USY zeolite as catalyst, a wide scope of alkenes and aromatic amines with various functional groups are smoothly converted into the corresponding products in 48–95% yields with high regioselectivity. Detailed characterizations revealed that Lewis acid can promote Hofmann-Martius rearrangement of hydroamination products toward hydroarylation products, resulting in high selectivity for hydroarylation products. In addition, it could be found that the weak acid sites of zeolite play a key role in forming hydroarylation products. Furthermore, the catalyst can be reused at least 10 times without obvious deactivation. This work may promote the development of heterogeneous catalyst system for alkene hydroarylation.

Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides

A highly regioselective Ni-catalyzed electrochemical reductive relay cross-coupling between an aryl halide and an alkyl halide has been developed in an undivided cell. Various functional groups are tolerated under these mild reaction conditions, which pro

Synthesis of diarylmethanes via metal-free reductive cross-coupling of diarylborinic acids with tosyl hydrazones

This paper describes a practical and efficient procedure that takes advantage of diarylborinic acids as a cost-effective alternative to arylboronic acids for synthesis of diarylmethanes through metal-free reductive cross-coupling with N-tosylhydrazones of aromatic aldehydes and ketones. The procedure tolerates hydroxyl, halide, amine, and allyl functionality, complementary to the transition-metal catalyzed cross-coupling techniques.

Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Bronsted acids

(Chemical Equation Presented) We have developed an environmentally benign synthetic approach to nucleophilic substitution reactions of alcohols that minimizes or eliminates the formation of byproducts, resulting in a highly atom-efficient chemical process. Proton- and metal-exchanged montmorillonites (H- and Mn+-mont) were prepared easily by treating Na +-mont with an aqueous solution of hydrogen chloride or metal salt, respectively. The H-mont possessed outstanding catalytic activity for nucleophilic substitution reactions of a variety of alcohols with anilines, because the unique acidity of the H-mont catalyst effectively prevents the neutralization by the basic anilines. In addition, amides, indoles, 1,3-dicarbonyl compounds, and allylsilane act as nucleophiles for the H-mont-catalyzed substitutions of alcohols, which allowed efficient formation of various C-N and C-C bonds. The solid H-mont was reusable without any appreciable loss in its catalytic activity and selectivity. Especially, an Al3+-mont showed high catalytic activity for the α-benzylation of 1,3-dicarbonyl compounds with primary alcohols due to cooperative catalysis between a protonic acid site and a Lewis acidic Al3+ species in its interlayer spaces.

Dicationic electrophiles from olefinic amines in superacid

This paper describes the superacid-catalyzed chemistry of olefinic amines and related compounds. A variety of olefinic amines are found to react with benzene in CF3SO3H (triflic acid) to give addition products in good yields (75-99%), including the pharmaceutical agents fenpiprane and prozapine. A general mechanism is proposed that invokes the formation of reactive, dicationic electrophiles and the direct observation of a diprotonated species is reported from low-temperature NMR experiments. This chemistry is also used to conveniently prepare functionalized polystyrene beads having pendant amine groups.

Catalytic alkylation of aromatic amines with styrene in the presence of cationic rhodium complexes and acid

The first transition metal-catalyzed Friedel-Crafts alkylation of aromatic amines with styrene is reported. ortho-Alkylation of anilines occurs using catalytic amounts of [Rh(cod)2]BF4/4 PPh3 and HBF4.

REACTIONS OF STYRENE WITH AROMATIC AMINES

In alkylation with styrene N,N-dimethylaniline in the presence of aluminum phenoxide, and aniline and N-methylaniline, also in the presence of aluminum phenoxide, as also of the corresponding hydrochlorides, usually form mixtures of mono(α-methylbenzyl)anilines, in which ortho-substitution products predominate.When aluminum phenoxide is used as catalyst, the yields of o-aralkylanilines attain 92-94percent.In the alkylation of N-methyl- and N,N-dimethyl-anilines demethylation and disproportionation occur.

Molecular Rearrangements: Part XIII-Thermal Rearrangement of N-(α-Phenethyl)aniline and N-(β-Phenethyl)aniline

Thermolysis of N-(α-phenethyl)-(I)- and N-(β-phenethyl)-(II)-anilines for ca. 7 days in the absence of promotors, results in the migration of phenethyl group to the aniline nucleus.Thermal rearrangement of II produces ethylbenzene, 1,4-diphenylbutane, 2,3-diphenylbutane, 2-phenylindole, aniline and 2- and 4-(α-phenethyl)anilines.A similar thermal rearrangement of I results in the same neutral products together with 2,3-diphenyl-2-butene.Thermolysis of I and II in the presence of isoquinoline affords, in addition to the above products, 1-(α-phenethyl)-isoquinoline.In the presence of β-naphthol, besides the normal products, 2,2'-dinapthol is obtained together with some heterocyclic compounds of unknown nature.The results have been interpreted in terms of a free radical mechanism.