10479-24-0

Upstream product

• 84395-76-6 (E)-N-benzyl-N-methyl-2-phenylethen-1-amine 
• 100-44-7 benzyl chloride 
• 589-08-2 N-Methyl-N-phenethylamine 
• 93-58-3 benzoic acid methyl ester 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 141538-44-5 N,N-dibenzyl-N-methyl(trimethylsilyl)methylammonium iodide 
• 100-42-5 styrene 
• 103-67-3 benzyl-methyl-amine 
• 100-52-7 benzaldehyde 
• 103-63-9 1-phenyl-2-bromoethane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 100-39-0 benzyl bromide 
• 60-12-8 2-phenylethanol 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 

Downstream Products

• 589-08-2 N-Methyl-N-phenethylamine 

Relevant academic research and scientific papers

Reagent concentration effects in the REM resin solid phase synthesis of tertiary amines

The use of reagent concentration has resulted in increased rates for all stages of the REM resin synthesis of tertiary amines. These increases in rate translate into faster reaction times, higher yields and lower reagent consumption. Of the methods examin

Ir-Catalyzed Ligand-Free Directed C-H Borylation of Arenes and Pharmaceuticals: Detailed Mechanistic Understanding

An efficient method for Ir-catalyzed ligand free ortho borylation of arenes (such as, 2-phenoxypyridines, 2-anilinopyridines, benzylamines, benzylpiperazines, benzylmorpholines, benzylpyrrolidine, benzylpiperidines, benzylazepanes, α-amino acid derivatives, aminophenylethane derivatives, and other important scaffolds) and pharmaceuticals has been developed. The reaction underwent via an interesting mechanistic pathway, as revealed by the detailed mechanistic investigations by using kinetic isotope studies and DFT calculations. The catalytic cycle is found to involve the intermediacy of an Ir-boryl complex where the substrate C-H activation is the turnover determining step, intriguingly without any appreciable primary KIE. The method displays a broad range of substrate scope and functional group tolerance. Numerous late-stage borylation of various important molecules and drugs were achieved using this developed strategy. The borylated compounds were further converted into more valuable functionalities. Moreover, utilizing the benefit of the B-N intramolecular interaction of the mono borylated compounds, an operationally simple method has been developed for the selective diborylation of 2-phenoxypyridines and numerous functionalized arenes. Furthermore, the synthetic utility has been showcased with the removal of the pyridyl directing group from the borylated product to achieve ortho borylated phenol along with the ipso-borylation for the preparation of 1,2-diborylated benzene.

Synthesis of Arylethylamines via C(sp3)-C(sp3) Palladium-Catalyzed Cross-Coupling

Substituted arylethylamines represent a key structural motif in natural, pharmaceutical, and agrochemical compounds. Access to such scaffolds has been the subject of long-standing synthetic interest. Herein, we report the synthesis of such scaffolds via a palladium-catalyzed C(sp3)-C(sp3) coupling between (chloromethyl)aryls and air-/moisture-stable N,N-dialkylaminomethyltrifluoroborate salts. Rapid hit identification was achieved using microscale high-throughput experimentation and was followed by millimolar-scale reaction parameter optimization. A range of structurally and electronically varied arylethylamine products were obtained in moderate to excellent yields (27-96%, >60 examples). The reaction mechanism is proposed to proceed via formation of a trialkylbenzylammonium species prior to oxidative addition.

Lithium-Catalyzed anti-Markovnikov Intermolecular Hydroamination Reactions of Vinylarenes and Simple Secondary Amines

Various β-arylethylamine derivatives were straightforwardly obtained by the lithium-catalyzed anti-Markovnikov selective intermolecular hydroamination reaction of secondary aliphatic amines with vinylarenes. The use of only 1.5 mol % LiCH2TMS as a solid base in THF proved to be efficient to deliver the target products at room temperature with up to complete conversions. Both reaction partners were, moreover, used in equivalent amounts; thus, this protocol best respects the concepts of sustainable chemistry for the easy preparation of lead structures for pharmaceutically active compounds.

Mild Hydrogenation of Amides to Amines over a Platinum-Vanadium Bimetallic Catalyst

Hydrogenation of amides to amines is an important reaction, but the need for high temperatures and H2 pressures is a problem. Catalysts that are effective under mild reaction conditions, that is, lower than 30 bar H2 and 70 °C, have not yet been reported. Here, the mild hydrogenation of amides was achieved for the first time by using a Pt-V bimetallic catalyst. Amide hydrogenation, at either 1 bar H2 at 70 °C or 5 bar H2 at room temperature was achieved using the bimetallic catalyst. The mild reaction conditions enable highly selective hydrogenation of various amides to the corresponding amines, while inhibiting arene hydrogenation. Catalyst characterization showed that the origin of the catalytic activity for the bimetallic catalyst is the oxophilic V-decorated Pt nanoparticles, which are 2 nm in diameter.

Anti-markovnikov hydroamination of aromatic alkenes with secondary amines catalyzed by easily accessible yttrium complexes

Binaphthylamido alkyl yttrium complexes have been proven to promote the anti-Markovnikov addition between various styrene derivatives and secondary amines efficiently. Although the reaction has to be performed at high temperature, it is realized advantage

Formal anti-markovnikov hydroamination of terminal aryl alkynes with pinacolborane and hydroxylamines via Zr/Cu sequential catalysis

We have explored a novel dry plasma process for the fabrication of electrodes on Nafion surfaces. Nanosized pillar structures were prepared through argon ion (Ar+) plasma treatment. The shear strengths of Au electrodes on plasma-treated Nafion surfaces were investigated. We found that the maximum shear strength (1.08 MPa) of Au-Nafion was observed under the optimal conditions (8 min, 100 W, 5 Pa, Ar+). Finally, we successfully prepared strongly bonded Au electrodes on Nafion through plasma surface treatment without using a wet plating process.

Broadening the scope of group 4 hydroamination catalysis using a tethered ureate ligand

(Chemical Equation Presented) A broadly applicable group-4-based precatalyst for the hydroamination of primary and secondary amines was developed. Screening experiments involving a series of amide and urea proligands led to the discovery of a tethered bis(ureate) zirconium complex with unprecedented reactivity in the intermolecular hydroamination of alkynes and the intramolecular hydroamination of alkenes. This catalyst system is effective with primary and secondary amines, 1,2-disubstituted alkenes, and heteroatom-containing functional groups, including ethers, silanes, amines, and heteroaromatics. The gem-disubstituent effect is not required for cyclization. The catalyst is generally regioselective for the anti-Markovnikov product of intermolecular alkyne hydroamination, and chemoselective for hydroamination over C-alkylation when forming 6- and 7-membered rings from aminoalkenes.

Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines

A versatile and highly atom economical catalytic system consisting of [Cp*IrCl2]2/NaHCO3 (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of amines with primary and secondary alcohols as alkylating reagents has been developed. For example, the reaction of equimolar amounts of aniline and benzyl alcohol in the presence of [Cp*IrCl2]2 (1.0 mol % Ir) and NaHCO3 (1.0 mol %) in toluene at 110 °C gives N-benzylaniline in 94% yield. The present catalytic system is applicable to the N-alkylation of both primary and secondary amines, and only harmless water is produced as co-product. A wide variety of secondary and tertiary amines can be synthesized with high atom economy under mild and less-toxic conditions. One-pot sequential N-alkylation leading to tertiary amines bearing three different substituents is also described.

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.