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Upstream product

• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 1823-91-2 1-phenylethyl cyanide 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 103-63-9 1-phenyl-2-bromoethane 
• 530-44-9 4-(Dimethylamino)benzophenone 
• 22057-80-3 1-[4-(dimethylamino)phenyl]-1-phenylethene 
• 768295-58-5 1-[4-(dimethylamino)phenyl]-1-phenylethanol 
• 121-69-7 N,N-dimethyl-aniline 
• 618-36-0 rac-methylbenzylamine 
• 100-42-5 styrene 

Relevant academic research and scientific papers

Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction

The first electrochemical approach for nickel-catalyzed cross-electrophile coupling was developed. This method provides a novel route to 1,1-diarylalkane derivatives from simple and readily available alkyl and aryl halides in good yields and excellent regioselectivity under mild conditions. The procedure shows good tolerance for a broad variety of functional groups and both primary and secondary alkyl halides can be used. Furthermore, the reaction was successfully scaled up to the multigram scale, thus indicating potential for industrial application. Mechanistic investigation suggested the formation of a nickel hydride in the electroreductive chain-walking arylation, which led to the development of a new nickel-catalyzed hydroarylation of styrenes to provide a series of 1,1-diaryl alkanes in good yields under mild reaction conditions.

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

Bisoxazoline-pincer ligated cobalt-catalyzed hydrogenation of alkenes

The efficient and atom economical hydrogenation of alkenes using a novel bisoxazoline ligated cobalt complex has been developed. The hydrogenation of a variety of alkenes containing electron neutral and electron-donating groups proceeds in high yield, whi

Iridium-Catalyzed Highly Efficient and Site-Selective Deoxygenation of Alcohols

An iridium-catalyzed, highly efficient, and site-selective deoxygenation of primary, secondary, and tertiary alcohols has been realized, under the assistance of a 4-(N-substituted amino)aryl directing group. Only the hydroxyl adjacent to the directing group can be deoxygenated. The deoxygenation is performed in water, with formic acid as both the promoter and hydride donor. Excellent yields and functionality tolerance, as well as high efficiency (S/C up to 1000 000, TOF up to 445 000 h-1), are obtained. The kinetic isotope effect studies show that hydride formation is the rate-determining step, and the deoxygenation follows an SN1-type pathway. The deoxygenation protocol has been demonstrated useful in the structural modification of naturally occurring ketones and steroids.

Gold-catalyzed hydroarylation of alkenes with dialkylanilines

Anti-Bredt di(amino)carbene supported gold(I) chloride complexes are readily prepared in two steps from the corresponding isocyanide complexes. In the presence of KB(C6F5)4as chloride scavenger, they promote the unprecedented hydroarylation reaction of alkenes with N,N-dialkylanilines with high para-selectivity. The latter are challenging arenes for Friedel-Craft reactions, due to their high basicity.

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.

PHOTOINDUCED ELECTRON TRANSFER BETWEEN AROMATIC AMINES AND ALKYL NITRILES.

Irradiation of aromatic amines in the presence of alkyl nitriles leads to efficient electron-transfer reactions, resulting in amination or alkylation of the aromatic moieties.

Kinetics and Mechanism of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 10. Reactions of s-Alkyl Primary Amines with Pyryliums

2,4,6-Triphenylpyrylium with s-alkylamines gives isolatable pyridiniums (which undergo SN2 substitution with nucleophiles and elimination to olefins). 2,4,6-triphenylpyrilium with 1-phenylethylamine and α-phenylbenzylamine forms the corresponding carbonium ions which may be trapped by nucleophiles.Isolated 1-cycloalkylbenzoquinoliniums (2) solvolyse by the SN1 mechanism (for five-, six- and seven-membered rings): for the cyclobutyl case an Sn2 reaction is also found.