79344-29-9

Upstream product

• 42070-98-4 1-(p-tolyl)ethylamine 
• 79344-38-0 1-phenyl-N-(1-(p-tolyl)ethylidene)methanamine 

Relevant academic research and scientific papers

Iron-catalyzed transfer hydrogenation of imines assisted by an iron-based Lewis acid

An iron-catalyzed transfer hydrogenation of N-aryl and N-alkyl imines using isopropanol as the hydrogen donor is reported for the first time. A combination of two iron complexes serving different roles is the key for the success of this catalytic system. As a result, an environmentally friendly and precious metal-free transfer hydrogenation of imines has been developed. The use of a suitable co-catalyst as an activator not only led to efficient transfer hydrogenation, but also showed potential in enantioselective transformation.

Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: The counteranion and solvent effects, and substrate scope

Asymmetric hydrogenation of N-alkyl and N-aryl ketimines catalyzed by chiral cationic η6-arene-(N-monosulfonylated diamine) Ru(II) complexes has been investigated. Strong counteranion and solvent effects on the enantioselectivity were observed. The ruthenium catalyst bearing non-coordinating BArF- anion was found to be particularly effective for the hydrogenation of acyclic and exocyclic N-alkyl ketimines in the presence of (Boc)2O in dichloromethane or even under solvent-free conditions, providing chiral amines with up to >99% ee and full conversions. Alternatively, the ruthenium catalyst bearing achiral phosphate anion together with corresponding phosphoric acid as the additive was also efficient for the hydrogenation of N-alkyl ketimines in the absence of (Boc)2O with excellent enantioselectivities and full conversions. For N-aryl ketimines lower enantiomeric excesses were observed by using the ruthenium catalyst bearing BArF- anion. This catalytic protocol thus provides a facile and practical access to optically active amines and has been successfully employed in the gram-scale synthesis of enantiomerically pure (+)-sertraline.

Preparation of N-benzylamines

N-Benzylamines are prepared by a process in which (i) in a first step, a benzaldehyde is reacted with a primary amine to give the imine and (ii) in a second step, the imine is hydrogenated with hydrogen in the presence of a catalyst containing one or more metals of groups 8 to 10 of the Periodic Table of the Elements to give the N-benzylamine, wherein the iminization (i) is carried out in a water-miscible solvent and the resulting water of reaction is not removed, and the hydrogenation (ii) is carried out in the imine solution obtained in the iminization (i) and containing water of reaction.