56249-61-7

Upstream product

• 123-72-8 butyraldehyde 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 71-36-3 butan-1-ol 
• 100-52-7 benzaldehyde 
• 109-73-9 N-butylamine 

Downstream Products

• 874491-74-4 3,5-diethyl-1-benzyl-2-propyl-1,2-dihydro-pyridine 
• 130412-87-2 1-phenyl-4-ethyl-2-aza-2,4-octadiene 
• 56249-49-1 2-(N-benzylamino)pentanenitrile 
• 25881-46-3 (1-Benzylamino-butyl)-ethyl-phosphinic acid 
• 25881-43-0 N-Benzyl-α-aminobutanphenylphosphinsaeure 
• 25881-33-8 (1-benzylamino-butyl)-phosphonic acid 
• 55-21-0 benzamide 
• 74926-39-9 1-phenyl-4-ethyl-2-aza-1,3-octadiene 
• 123-72-8 butyraldehyde 
• 1077-18-5 N-benzylidenebutan-1-amine 
• 90496-20-1 Benzyl-(1-propyl-pentyl)-amine 
• 24764-97-4 2-bromobutanal 

Relevant academic research and scientific papers

Mechanical Force for the Transformation of Aziridine into Imine

Force-selective mechanochemical reactions may be important for applications in polymer mechanochemistry, yet it is difficult to achieve such reactions. This paper reports that cis-N-phthalimidoaziridine incorporated into a macromolecular backbone undergoes migration of N-phthalimido group to afford imine under mechanochemical condition and not thermal one. The imine is further hydrolyzed by water bifurcating into amine and aldehyde. These structural transformations are confirmed by 1H NMR and FT-IR spectroscopic analyses. Computational simulations are conducted for the aziridine mechanophore to propose the mechanism of reaction and define the substrate scope of reaction.

Base-Free Oxidative Coupling of Amines and Aliphatic Alcohols to Imines over Au–Pd/ZrO2 Catalyst under Mild Conditions

Abstract: The base-free synthesis of imines from amines and aliphatic alcohols over Au–Pd alloy catalysts under ambient conditions was developed. A series of Au–Pd/ZrO2 bimetallic catalysts with varying metal loadings and Au?:?Pd molar ratios were prepared and their catalytic performance was investigated. The 3.0?wt?% Au–Pd/ZrO2 alloy catalyst with Au?:?Pd molar ratio of 1?:?1 showed the best catalytic performance. Under air atmosphere, various imines were obtained from coupling of amines and aliphatic alcohols without any additives or promoters. The performance of alloy NPs was superior to that of monometallic catalysts due to the synergistic effect which was demonstrated by TEM, XPS, and UV–Vis characterization. Our work suggested this transformation differed slightly from those reactions between amine and benzyl alcohol and a possible mechanism was proposed. Moreover, the Au–Pd/ZrO2 catalyst could be easily separated and reused for at least five successive runs with high catalytic activity.

Fe2Mn(μ3-O)(COO)6 Cluster Based Stable MOF for Oxidative Coupling of Amines via Heterometallic Synergy

The direct catalytic oxidative coupling of amines is one of the attracting methods for the synthesis of a variety of pharmaceutical or industrial needed imines. Numerous earth-abundant manganese based salts, oxides, and complexes have been applied in this reaction. However, these compounds suffered from difficult separation, large catalyst loading, complicated reactivation or indeterminate activity. Considering the facts that metal-organic frameworks (MOFs) with crystalline structure, precise composition, and enormous surface area have superior performance in heterogeneous catalytic reactions, herein, we introduced Mn into [Fe3(μ3-O)(CH3COO)6], one of the precursors for the preparation of stable MOFs, and got [Fe2Mn(μ3-O)(CH3COO)6] cluster. After ligand replacement with biphenyl-3,4’,5-tricarboxylic acid (BPTC), heterometallic cluster-based [Fe2Mn(μ3-O)(BPTC)2(DMF)2(H2O)] (1) was obtained. As expected, 1 is stable and able to catalyze the homo- or cross-coupling of amines effectively and selectively with 0.9 mol% catalyst loading at room temperature. Control experiments indicated that the catalytic activity of 1 mainly stems from Mn sites and that Fe synergistically contributes to the stability. Additionally, 1 is recyclable and can be reused easily for at least 8 runs without obvious decrease in catalytic ability. To our knowledge, 1 should be the first heterometallic cluster-based MOF with defined structure suitable for the synthesis of diverse imines from oxidative coupling of amines under mild conditions, which may shed light on the easy preparation of effective heterogeneous catalysts for organic synthesis.

Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4

An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.

Metal-Ligand Cooperation Facilitates Bond Activation and Catalytic Hydrogenation with Zinc Pincer Complexes

A series of PNP zinc pincer complexes capable of bond activation via aromatization/dearomatization metal-ligand cooperation (MLC) were prepared and characterized. Reversible heterolytic N-H and H-H bond activation by MLC is shown, in which hemilability of the phosphorus linkers plays a key role. Utilizing this zinc pincer system, base-free catalytic hydrogenation of imines and ketones is demonstrated. A detailed mechanistic study supported by computation implicates the key role of MLC in facilitating effective catalysis. This approach offers a new strategy for (de)hydrogenation and other catalytic transformations mediated by zinc and other main group metals.

Activation of primary amines by copper(i)-based lewis acid promoters in the solventless synthesis of secondary propargylamines

Primary amines are activated by copper(I)-based Lewis acid promoters in an A 3 -coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO 4 /NaI system, a practical precursor of the in situ generated effective CuI/I 2 system, that worked well, but only in a restricted number of examples. Substitution of I 2 with CeCl 3 ·7H 2 O in a one-pot two-step reaction provided good yields and a wider applicability, with the added value given by a safer procedure.

Aerobic oxidative coupling of alcohols and amines towards imine formation by a dicopper(I,I) catalyst

A dicopper(I,I) complex [Cu2(L1) (Cl)2] (1), bearing a Cu2Cl2 core spanned by a naphthyridine–diimine ligand is synthesized by the treatment of CuCl with 2,7–bis(N–mesitylmethylimino)–1,8–naphthyridine (L1). The catalytic efficacy of 1 is assessed for aerobic oxidative synthesis of imines from alcohols and amines. The title complex is found to be an excellent catalyst for a wide variety of alcohols and amines. Kinetic experiments revealed the involvement of both copper ions in the aerobic oxidation process. The general utility of naphthyridine based ligands to favour a possible bimetallic pathway for a catalytic reaction is demonstrated here.

Synthesis of imines from amines in aliphatic alcohols on Pd/ZrO2 catalyst under ambient conditions

Synthesis of imines from amines and aliphatic alcohols (C 1-C6) in the presence of base on supported palladium nanoparticles has been achieved for the first time. The catalytic system shows high activity and selectivity in open air at room temperature.

Synthesis and pharmacological properties of 5-alkyl substituted nicotine analogs

This paper describes a concise and practical route to enantiomerically enriched 5-alkyl substituted nicotine analogs. The Vilsmeier reaction was used to construct the nicotinaldehydes ring followed by the introduction of the chiral homoallylic alcohol by organic boron reagent and the cyclization of the pyrrolidine ring through the reduction of a chiral azide. 17 analogs have been synthesized and their corresponding biological activities were tested, in which compounds 10d and 10g exhibit excellent IC50 values against RD and SY-SY5Y. Copyright

Efficient Iridium-thioether-dithiolate catalyst for β-alkylation of alcohols and selective imine formation via N-alkylation reactions

An Ir-thioether-dithiolate complex, [Cp*Ir(η3-tpdt)] (Cp* = η5-C5Me5, tpdt = S(CH 2CH2S-)2), is evaluated for its catalytic potential in the β-alkylation of secondary alcohols and the N-alkylation of amines with alcohols. The β-alkylation reaction proceeded efficiently under low catalyst loading and in the absence of any sacrificial hydrogen additive with only water being formed as the coproduct. The same complex also proved to be efficient in the synthesis of imines via the N-alkylation reaction. The predominant formation of imines, rather than amines, in this reaction is a deviation from the product selectivity usually observed in similar N-alkylation reactions involving organometallic catalysts.