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Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 77287-34-4 formamide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 100-47-0 benzonitrile 
• 638-14-2 2,4,6-trimethyl-[1,3,5]triazinane 
• 824-94-2 p-methoxybenzyl chloride 
• 2393-23-9 4-methoxy-benzylamine 
• 100-51-6 benzyl alcohol 
• 60-35-5 acetamide 

Relevant academic research and scientific papers

Polymeric bimetallic catalyst-promoted in-water dehydrative alkylation of ammonia and amines with alcohols

A dehydrative alkylation with three kinds of Ir/B heterobimetallic polymeric catalysts in water is reported. The polymeric heterobimetallic catalysts were readily prepared by ionic convolution of a poly(catechol borate) and iridium complexes. The N-alkylation of ammonia and amines with alcohols, as alkylating agents, was carried out with a heterogeneous catalyst (1 mol% Ir) at 100 °C without the use of organic solvents under aerobic and aqueous conditions to afford the corresponding alkylated amines in high yield. Georg Thieme Verlag Stuttgart New York.

Cu(II) mediated generation and spectroscopic study of the tris(4-anisyl)amine radical cation and dication. Unusually shielded chemical shifts in the dication

The reaction of tris(4-anisyl)amine (TAA) with Cu2+ ion leading to formation of the TAA radical cation and dication is described. Spectroscopic studies confirm the formation of the radical cation and dication. 1H and 13C N

Reductive Amidation without an External Hydrogen Source Using Rhodium on Carbon Matrix as a Catalyst

An efficient method for preparation of secondary amides from primary amides and aldehydes using rhodium on carbon matrix as catalyst was developed. The method does not require any external hydrogen source and carbon monoxide is used as a reducing agent. The most active rhodium catalysts were characterized by BET, TEM and XPS techniques. Unexpectedly, it was found that heterogeneous rhodium on carbon matrix works as precatalyst for homogenous active species due to leaching of rhodium to the solution. Various secondary amides were synthesized and checked for antifungal activity. 4-Methoxy-N-(4-methoxybenzyl)benzamide demonstrated promising activity against Rhizoctonia Solani.

Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions

Herein, an efficient and green method for the selective synthesis of tertiary amines has been developed that involves iridium-catalyzed alkylation of various primary amines with aromatic or aliphatic alcohols. Notably, the catalytic protocol enables this transformation in the absence of additional base and solvent. Furthermore, the alkylation of nitrobenzene with primary alcohol to tertiary amine has also been achieved by the same catalytic system. Deuterium-labeling experiments and a series of control experiments were conducted, and the results suggested that an intermolecular borrowing hydrogen pathway might exist in the alkylation process.

Triazolylidene-Iridium Complexes with a Pendant Pyridyl Group for Cooperative Metal–Ligand Induced Catalytic Dehydrogenation of Amines

Two iridium(III) complexes containing a C,N-bidentate pyridyl-triazolylidene ligand were prepared that are structurally very similar but differ in their pendant substituent. Whereas complex 1 contains a non-coordinating pyridyl unit, complex 2 has a phenyl group on the triazolylidene substituent. The presence of the basic pyridyl unit has distinct effects on the catalytic activity of the complex in the oxidative dehydrogenation of benzylic amines, inducing generally higher rates, higher selectivity towards formation of imines versus secondary amines, and notable quantities of tertiary amines when compared to the phenyl-functionalized analogue. The role of the pyridyl functionality has been elucidated from a set of stoichiometric experiments, which demonstrate hydrogen bonding between the pendant pyridyl unit and the amine protons of the substrate. Such Npyr???H?N interactions are demonstrated by X-ray diffraction analysis, 1H NMR, and IR spectroscopy, and suggest a pathway of substrate bond-activation that involves concerted substrate binding through the Lewis acidic iridium center and the Lewis basic pyridyl site appended to the triazolylidene ligand, in agreement with ligand–metal cooperative substrate activation.

Palladium nanoparticles stabilised by cinchona-based alkaloids in glycerol: Efficient catalysts for surface assisted processes

Palladium nanoparticles (PdNPs) were synthesised and fully characterised, both in solution and the solid state, using naturally-occurring cinchona-based alkaloids in neat glycerol. These nano-systems were stable under reaction conditions, finding applications in hydrogenation and hydrodehalogenation processes, as a result of their surface-like behaviour. Their reactivity was improved in relation to that involving PdNPs stabilised by phosphines and also by Pd/C as a heterogenous catalyst, mainly in terms of recyclability. In particular, the colloidal palladium catalyst stabilised by quinidine was highly efficient to promote the hydrodechlorination of aromatic compounds under low dihydrogen pressure. These original catalysts found applications in the synthesis of secondary and tertiary amines including N-substituted anilines, by means of one-pot tandem Pd-catalysed methodologies under smooth conditions. In all of these processes, glycerol performed a crucial function as a liquid support for the immobilisation of nanoparticle-based catalysts, allowing both the stabilisation of the nano-catalysts and easy recycling of the catalytic phase.

Tris(8-methoxy-2-quinolylmethyl)amine (8-MeOTQA) as a highly fluorescent Zn2+ probe prepared by convenient C3-symmetric tripodal amine synthesis

A convenient synthesis of C3-symmetric tribenzylamine (TBA) derivatives has been investigated. The reaction of benzyl chlorides with acetaldehyde ammonia trimer (1) in the presence of base afforded tribenzylamines in high yields. This efficient method allows the diverse synthesis of TPA (tris(2-pyridylmethyl)amine) and TQA (tris(2-quinolylmethyl)amine) derivatives. Among the TQA compounds prepared, tris(8-methoxy-2-quinolylmethyl)amine (8-MeOTQA, 4) exhibited superior properties as a fluorescent zinc probe with high quantum yield (Zn = 0.51) and high sensitivity (limit of detection (LOD) = 3.4 nM). The X-ray crystallographic analysis of [Zn(8-MeOTQA)]2+ revealed that the steric and electronic effect of 8-methoxy substituents kicks out the solvent and counterion molecules from the metal coordination sphere, resulting in short Zn-Nquinoline coordination distances (2.04-2.07 ?). The pseudo hexacoordinate complex of 6-methoxy derivative, [Zn(6-MeOTQA)(DMF)(ClO4)]+, exhibited longer Zn-Nquinoline distances (2.07-2.19 ?) and much smaller fluorescence intensity (Zn = 0.027). The replacement of one of the three 8-methoxyquinolines with pyridine also afforded much less fluorescent zinc complex (Zn = 0.095) due to the solvent coordination (Zn-Nquinoline = 2.05-2.18 ? for [Zn(8-MeOBQPA)(CH3OH)]2+).

Highly efficient heterogeneous gold-catalyzed direct synthesis of tertiary and secondary amines from alcohols and urea

Urea, the white gold: The efficient synthesis of tertiary and secondary amines is achieved by heterogeneous gold-catalyzed direct amination of stoichiometric alcohols with urea in good to excellent yields. Via a hydrogen autotransfer pathway, the reactions of primary alcohols with urea give tertiary amines exclusively, while secondary alcohols selectively afford secondary amines.

Ruthenium-catalyzed formation of tertiary amines from nitriles and alcohols

A ruthenium-catalyzed tertiary-amine formation was developed using the borrowing hydrogen strategy. Various tertiary amines were obtained efficiently from nitriles and primary alcohols. Two possible pathways were found for the tertiaryamine formation under RuCl3/dppf catalytic conditions. The nitriles mainly act as a nitrogen source in this kind of transformation.