123330-53-0

Upstream product

• 372-19-0 meta-fluoroaniline 
• 100-44-7 benzyl chloride 
• 72595-18-7 3-fluoro-N-[phenylmethylidene]aniline 
• 100-52-7 benzaldehyde 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 100-46-9 benzylamine 
• 164362-52-1 N-benzylidene-m-fluoroaniline 
• 768-35-4 3-fluorophenylboronic acid 
• 622-79-7 benzyl azide 
• 100-51-6 benzyl alcohol 
• 1073-06-9 3-fluorobromobenzene 
• 108-88-3 toluene 

Downstream Products

• 263340-19-8 3-[(3-fluorophenyl)[phenylmethyl]amino]-1,1,1-trifluoro-2-propanol 
• 1436432-47-1 1-benzyl-7-fluoro-3-hydroxy-4-methylquinolin-2(1H)-one 
• 1436432-57-3 N-benzyl-N-(3-fluorophenyl)-3-oxobutanamide 
• 1436432-66-4 (Z)-N-benzyl-N-(3-fluorophenyl)-3-hydroxybut-2-enamide 
• 880256-29-1 2-{[benzyl-(3-fluoro-phenyl)-carbamoyl]-methylene}-malonic acid diethyl ester 
• 263347-01-9 3-[3-fluorophenyl[3-(trifluoromethyl)benzoyl]amino]-1,1,1-trifluoro-2-propyl benzoate 
• 263349-58-2 3-[(3-fluorophenyl)amino]-1,1,1-trifluoro-2-propanol 

Relevant academic research and scientific papers

Iron-Catalyzed Oxidative Amination of Benzylic C(sp3)–H Bonds with Anilines

Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr4] showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr4] was more efficient for EDG-substituted anilines. This work provides alternative access to benzylamines with the advantages of both a wide substrate scope and iron catalysis.

Convenient and Reusable Manganese-Based Nanocatalyst for Amination of Alcohols

The development of new sustainable nanocatalytic systems for green chemical synthesis is a growing area in chemical science. Herein, a reusable heterogeneous N-doped graphene-based manganese nanocatalyst (Mn@NrGO) for selective N-alkylation of amines with alcohols is described. Mechanistic studies illustrate that the catalytic reaction follows a domino dehydrogenation-condensation-hydrogenation sequence of alcohols and amines with the formation of water as the sole by-product. The scope of the reaction is extended to the synthesis of pharmaceutically important N-alkylated amine intermediates. The heterogeneous nature of the catalyst made it easy to separate for long-term performance, and the recycling study revealed that the catalyst was robust and retained its activity after several recycling experiments.

Thiazoline-Iridium (III) Complexes and Immobilized Nanomaterials as Selective Catalysts in N-Alkylation of Amines with Alcohols

In this research, a new series of thiazoline-iridium (III) complexes (4–7) derived from cysteine were prepared and fully characterized by conventional methods. The molecular structure of complex 5 was also determined by single-crystal X-ray diffraction. These complexes were evaluated as catalysts for hydrogen-borrowing reactions of amines with alcohols. In particular, complex 5 showed the best activity as catalyst. Various amines have been alkylated with alcohols affording moderate to good yield (33–99%). Moreover, the immobilized nanomaterials (M1,2) were fabricated by sonication process from the best catalyst 5 with the multi-walled carbon nanotubes (MWCNTs) and graphene oxide (GO), respectively, and characterized by X-ray diffraction (XRD), Fourier transform infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) spectroscopy, and inductively coupled plasma-mass spectrometry (ICP-MS). The M1,2 nanomaterials were also tested as catalysts in model catalytic reaction for N-alkylation. The M1 nanomaterial showed significantly higher activity than the M2 nanomaterial. The M1 catalyst was recovered by filtration and reused for four catalytic cycles with high conversion (99%, 97%, 96%, and 86%).

A Highly Active PN3 Manganese Pincer Complex Performing N-Alkylation of Amines under Mild Conditions

A highly active Mn(I) catalyst based on a nonsymmetric PN3-ligand scaffold for the N-alkylation of amines with alcohols utilizing the borrowing hydrogen methodology is reported. A broad range of anilines and the more challenging aliphatic amines were alkylated with primary and secondary alcohols. Moreover, the combination of low catalyst loadings and mild reaction conditions provides high efficiency for this atom-economic transformation.

A nanoscale iron catalyst for heterogeneous direct: N - And C -alkylations of anilines and ketones using alcohols under hydrogen autotransfer conditions

Here, we report a commercially available nanoscale Fe catalyst for heterogeneous direct N- and C-alkylation reactions of anilines and methyl ketones with alcohols. A hydrogen autotransfer mechanism has been found to operate in these reactions by deuterium labelling studies. In addition, dehydrogenative quinoline synthesis has been demonstrated from amino benzyl alcohols and acetophenones.

Direct access to: N -alkylated amines and imines via acceptorless dehydrogenative coupling catalyzed by a cobalt(ii)-NNN pincer complex

A simple, phosphine-free Co(ii)-NNN pincer complex catalyzed direct N-alkylation of anilines with alcohols via hydrogen auto-transfer (HA) and selective acceptorless dehydrogenative coupling (ADC) of benzylamines with alcohols affording imines with the liberation of molecular hydrogen and water is reported.

Manganese catalyzed N-alkylation of anilines with alcohols: Ligand enabled selectivity

Ligand enabled Earth-abundant manganese catalyzed N-alkylation of amines with alcohols via a hydrogen auto-transfer strategy is reported. The choice of the ligand plays a significant role in the alcohol reactivity (aliphatic or aromatic) toward N-alkylation reactions.

Copper-catalyzed radical reactions of 2-azido-N-arylacrylamides with 1-(trifluoromethyl)-1,2-benziodoxole and 1-azidyl-1,2-benziodoxole

The reactions of 2-azido-N-arylacrylamides with trifluoromethyl radicals and azidyl radicals were investigated by using Togni's reagent and Zhdankin's reagent as the source of these radicals. Under the catalysis of CuI, Togni's reagent was firstly converted into the trifluoromethyl radical, which then reacted with 2-azido-N-arylacrylamides to afford the corresponding α-(arylaminocarbonyl)iminyl radicals. The cyclization of the iminyl radicals delivered quinoxalin-2(1H)-one products in moderate yields. A similar reaction took place between 2-azido-N-arylacrylamides and the azidyl radical. In the latter cases, the reaction produced 3-azidomethyl and 3-cyano-subsituted quinoxalin-2(1H)-ones. This study not only helps elucidate the factors influencing the cyclization of α-(arylaminocarbonyl)iminyl radicals, but also provides a new approach towards quinoxalin-2-ones.

d-Glucose: An Efficient Reducing Agent for a Copper(II)-Mediated Arylation of Primary Amines in Water

A copper-catalyzed Ullmann-type amination with primary amines in water with a combination of copper(II) triflate [Cu(OTf)2], dipivaloylmethane, and d-glucose is reported. The mild conditions and the use of an inexpensive catalyst as well as a renewable feedstock (d-glucose and the surfactant TPGS-750-M, which is derived from vitamin E) make this protocol a safe and convenient strategy for efficient C?N bond formation. This easy-to-handle procedure is extremely competitive compared to palladium-based reactions and may be used to synthesize N-containing molecules, such as drugs or organic light-emitting diodes (OLEDs).

Pd@[nBu4][Br] as a simple catalytic system for N-alkylation reactions with alcohols

Palladium nanoparticles, simply and briefly generated in commercial and cheap onium salts using supercritical carbon dioxide, have been found to be an effective catalytic system for additive free N-alkylation reaction using alcohols via cascade oxidation/condensation/reduction steps.