28059-49-6

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 100-61-8 N-methylaniline 
• 920-39-8 isopropylmagnesium bromide 
• 50-00-0 formaldehyd 
• 6921-34-2 benzylmagnesium chloride 
• 40669-47-4 N-methyl-N,2-diphenylacetamide 
• 103-70-8 Formanilid 
• 103-82-2 phenylacetic acid 
• 62-53-3 aniline 
• 17376-04-4 2-phenethyl iodide 
• 60-12-8 2-phenylethanol 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 108-90-7 chlorobenzene 
• 589-08-2 N-Methyl-N-phenethylamine 

Downstream Products

• 92645-89-1 1-phenyl-2-(2-methylaminophenyl)ethane 
• 33383-97-0 p-(β-phenethyl)-N-methylaniline 
• 104903-68-6 N-methyl-4-(1-phenylethyl)aniline 
• 55116-81-9 N-methyl-N-[1-phenyl-2-(phenyl)ethyl]amine 
• 6068-87-7 Phenyl-2-phenylaethyldimethylammoniumbromid 
• 74-83-9 methyl bromide 
• 103-63-9 1-phenyl-2-bromoethane 
• 1309568-63-5 2-{4-[methyl(phenethyl)amino]phenyl}ethene-1,1,2-tricarbonitrile 

Relevant academic research and scientific papers

Base-Mediated Site-Selective Hydroamination of Alkenes

We present a base-mediated hydroamination protocol, using substoichiometric amounts of a hydrosilane and potassium tertbutoxide, that operates under mild conditions at 30 °C. Many aryl- and heteroatom-substituted olefins as well as arylamines are tolerated, affording the desired products with complete regioselectivity. Preliminary mechanistic investigations reveal a non-radical pathway for hydroamination. A sequential remote hydroamination strategy involving an initial Fe-catalysed olefin isomerisation followed by our base-mediated hydroamination was also developed to directly access-arylamines from terminal aliphatic alkenes.

Visible light-induced N-methyl activation of unsymmetric tertiary amines

In the presence of methylene group, selective N-methyl activation of tertiary amines has been accomplished with the aid of visible light using organic photocatalyst under air. This protocol explores numerous aliphatic and aromatic substituted tetra-hydroquinoline analogues from various tertiary amines and maleimides. Furthermore, this approach was applied to activate the methyl group of N-methyl carbazole to generate the biologically active molecule.

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

Robust Buchwald-Hartwig amination enabled by ball-milling

An operationally simple mechanochemical method for the Pd catalysed Buchwald-Hartwig amination of arylhalides with secondary amines has been developed using a Pd PEPPSI catalyst system. The system is demonstrated on 30 substrates and applied in the context of a target synthesis. Furthermore, the performance of the reaction under aerobic conditions has been probed under traditional solution and mechanochemical conditions, the observations are discussed herein.

A Catalyst-Free Amination of Functional Organolithium Reagents by Flow Chemistry

Reported is the electrophilic amination of functional organolithium intermediates with well-designed aminating reagents under mild reaction conditions using flow microreactors. The aminating reagents were optimized to achieve efficient C?N bond formation without using any catalyst. The electrophilic amination reactions of functionalized aryllithiums were successfully conducted under mild reaction conditions, within 1 minute, by using flow microreactors. The aminating reagent was also prepared by the flow method. Based on stopped-flow NMR analysis, the reaction time for the preparation of the aminating reagent was quickly optimized without the necessity of work-up. Integrated one-flow synthesis consisting of the generation of an aryllithium, the preparation of an aminating reagent, and their combined reaction was successfully achieved to give the desired amine within 5 minutes of total reaction time.

Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids

A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three commercial medicinal compounds, Butenafine, Cinacalcet. and Piribedil, in a one-pot manner without using any metal catalysts.

Catalytic N-Alkylation of Amines Using Carboxylic Acids and Molecular Hydrogen

A convenient, practical and green N-alkylation of amines has been accomplished by applying readily available carboxylic acids in the presence of molecular hydrogen. Applying an in situ formed ruthenium/triphos complex and an organic acid as cocatalyst, a broad range of alkylated secondary and tertiary amines are obtained in good to excellent yields. This novel method is also successfully applied for the synthesis of unsymmetrically substituted N-methyl/alkyl anilines through a direct three-component coupling reaction of the corresponding amines, carboxylic acids, and CO2 as a C1 source.

Formal anti-Markovnikov hydroamination of terminal olefins

A new strategy to access linear amines from terminal olefin precursors is reported. This two-step, one-pot hydroamination methodology employs sequential oxidation and reduction catalytic cycles. The formal hydroamination transformation proceeds with excellent regioselectivity, and only the anti-Markovnikov product is observed. Up to 70% yield can be obtained from styrenes or aliphatic olefins and either primary or secondary aromatic amines. Additionally, the scope is broad with respect to the olefin and accommodates a variety of functionalities; we demonstrate that amines with removable aryl protecting groups may be utilized to allow access to a more diverse array of hydroamination adducts.

Potassium hydroxide catalyzed addition of arylamines to styrenes

Potassium hydroxide is a competent and cheap catalyst for the intermolecular addition of arylamines to styrenes. The reactions are performed in nontoxic dimethyl sulfoxide and can be used for the large-scale synthesis of β-phenylethylamines. Georg Thieme Verlag Stuttgart - New York.

Base-catalyzed anti-Markovnikov hydroamination of vinylarenes - Scope, limitations and computational studies

The hydroamination of vinylarenes with primary and secondary amines was studied with catalytic amounts as low as 2 mol-% of LiN(SiMe3) 2/TMEDA. Reactions proceeded readily at 120°C in the absence of solvent to give selective anti-Markovnikov addition. Slow addition was observed at 25°C with either electron-deficient p-chlorostyrene or secondary cyclic amines such as pyrrolidine, piperidine, or morpholine. Primary amines were prone to a second hydroamination reaction to form tertiary amine byproducts. The selectivity for the mono(hydroamination) products could be improved with a two-fold excess of the amine. KN(SiMe3)2 showed higher catalytic activity but lower selectivity in comparison to that of LiN(SiMe 3)2, resulting in undesired C-H-activation by-products. The mechanism of the lithium-catalyzed hydroamination and the influence of TMEDA was studied with density functional theory. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.