87884-66-0

Upstream product

• 103-49-1 dibenzylamine 
• 100-47-0 benzonitrile 

Downstream Products

• 780-25-6 N-benzylidene benzylamine 

Relevant academic research and scientific papers

Highly efficient aerobic oxidation of various amines using Pd3Pb intermetallic compounds as catalysts

Intermetallic Pd3Pb supported on Al2O3 can act as a highly efficient heterogeneous catalyst for the oxidation of various amines including primary, secondary, aromatic, aliphatic, and cyclic amines. The Royal Society of Chemistry 2014.

Chemoselective transfer hydrogenation of nitriles to secondary amines with nickel(II) catalysts

Herein we report the selective transfer hydrogenation (TH) of nitriles to secondary (2°) amines with simple Ni(II)-catalysts using ammonia borane (AB) as a source of hydrogen (H2). A bis(pyrazolylmethyl)pyridine (L1) or ethylenediamine (L4) ligated Ni(II) pre-catalyst, created in situ, could hydrogenate several aromatic- and aliphatic nitriles in full conversions and isolated yields of up to 88% under ambient temperature and in very short reaction times. Deuterium labelling experiments illustrated the incorporation of a proton on the nitrogen and hydride on the α-carbon of dibenzylamine. Using α-picoline borane, containing no dissociable protons, assisted with the postulation of a two-step TH mechanism of benzonitrile. AB was subjected to dehydrogenation and it was observed that a maximum of 2.96 equivalents of H2 gas could be generated from NiCl2?6H2O/L1.

Enantioselective Formal Vinylogous N-H Insertion of Secondary Aliphatic Amines Catalyzed by a High-Spin Cobalt(II) Complex

Vinylcarbene insertion into the nitrogen-hydrogen (N-H) bond of amines allows direct access to α,β-unsaturated γ-amino acid derivatives, meeting a marked challenge in the control of regio- and enantioselectivities. Here, we report a highly γ-selective and enantioselective insertion into N-H bonds of aliphatic or aromatic secondary amines with vinyl substituted α-diazo pyrazoleamides using a high-spin chiralN,N′-dioxide/cobalt(II) complex catalyst. The method affords a wide variety of valuable optically activeZ- andE-type vinyl γ-amino amides. Calculation reveals a spin state change from the quartet cobalt(II) complex to a doublet Co(II)-carbene species for facileZ-selective and enantioselective nucleophilic addition.

Substrate-Controlled Divergent Synthesis of Enaminones and Pyrroles from Indolizines and Nitroso Compounds

It is imperative to learn new synthetic transformations to succeed in drug discovery and development. We report the substrate-driven synthesis of β-enaminones and N-aryl pyrroles from indolizines and nitrosoarenes; aryl-substituted indolizines lead to β-enaminones in a regio- and diastereoselective manner, whereas alkyl-substituted indolizines produce tetrasubstituted pyrroles. All products contain a pyridine unit, the second most abundant ring (after phenyl) in the FDA Orange Book. In both cases, the reactions proceed at room temperature without any catalyst. Moreover, both types of products can be obtained in one pot from commercial materials as well as at a gram scale. It is worthy of note that the regioselectivity of the β-enaminones is inaccessible by the standard literature methods and their utility has been exemplified in the synthesis of diverse heterocycles. We have made every endeavor to put forward the corresponding reaction mechanisms based on thorough experimental work. (Figure presented.).

Mechanistic study on aerobic oxidation of amine over intermetallic Pd3Pb: Concerted promotion effects by Pb and support basicity

A mechanistic study on aerobic oxidation of amine to imine over Pd3Pb/MOx (MOx = SiO2, TiO2, Al2O3, and MgO) intermetallic catalysts was performed to clarify the role of Pb and the support in enhancing catalytic activity. Results from X-ray absorption and photoelectron spectroscopies revealed that formation of the Pd3Pb phase made Pd electron-rich compared to pure Pd, whereas the electronic states of Pd in Pd3Pb/MOx were identical and independent of the nature of the support. Kinetic studies indicated that desorption of imine was promoted by Pb and that adsorption of amine was accelerated by basic sites on the support. Infrared temperature programmed desorption (IR-TPD) experiments demonstrated that desorption of imine was indeed promoted on Pd3Pb compared to Pd. The support effect only appears on Pd3Pb catalysts and not on pure Pd due to change in the rate-determining step from imine desorption to amine adsorption. The combination of Pb and the support basicity provides a unique and highly efficient bifunctional catalysis. (Chemical Equation Presented).