64309-86-0

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 77287-34-4 formamide 
• 121238-82-2 tris(benzotriazol-1-ylmethyl)amine 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 4484-74-6 4-methylbenzyl iodide 
• 17271-89-5 4-methylphenylmethylazide 
• 589-18-4 4-Methylbenzyl alcohol 
• 104-84-7 para-methylbenzylamine 
• 811-98-3 d⁽⁴⁾-methanol 
• 55-21-0 benzamide 
• 67-56-1 methanol 

Downstream Products

• 104-85-8 para-methylbenzonitrile 

Relevant academic research and scientific papers

Dichotomy of Atom-Economical Hydrogen-Free Reductive Amidation vs Exhaustive Reductive Amination

Rh-catalyzed one-step reductive amidation of aldehydes has been developed. The protocol does not require an external hydrogen source and employs carbon monoxide as a deoxygenative agent. The direction of the reaction can be altered simply by changing the solvent: reaction in THF leads to amides, whereas methanol favors formation of tertiary amines.

Rapid Multialkylation of Aqueous Ammonia with Alcohols by Heterogeneous Iridium Catalyst under Simple Conditions

This paper reports the synthesis of tertiary and secondary amines from aqueous ammonia and benzylic alcohols by titania-supported iridium catalyst. It is a successful example of heterogeneous systems at moderate temperature without either additional solvent or high pressure. The catalytic system showed good tolerance to the atmosphere condition and performed rapidly to give tribenzylamine a yield of over 99 % within 6 hours in argon. The crystal structure of titania supports for iridium catalysts strongly affected their activity. The catalysis smoothly proceeded on larger scales. The catalyst could be easily reused and run at least for 5 cycles without significant loss of activity. The highly-dispersed iridium species of less than 2 nm in diameter would be responsible for the excellent catalytic activity. This catalyst is well applicable in multialkylation of aqueous ammonia with various primary and secondary benzylic alcohols.

One-Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant

Rh-catalyzed one-step synthesis of tertiary and secondary amines from aldehydes and ketones, ammonium carbonate serving as nitrogen source, and carbon monoxide as a reducing agent has been developed. Aliphatic and aromatic aldehydes lead to the corresponding tertiary symmetrical amines in 69–83 % yields. Aromatic and aliphatic ketones lead to the corresponding secondary symmetrical amines which were obtained in 62–79 % yields.

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.

Simple Metal-Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

This work describes the use of cheap, safe, and easy-to-handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal-free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability. (Figure presented.).

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.

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.

In-water dehydrative alkylation of ammonia and amines with alcohols by a polymeric bimetallic catalyst

An in-water dehydrative alkylation with a novel heterobimetallic polymeric catalyst is described. Thus, a boron-iridium heterobimetallic polymeric catalyst was prepared by ionic convolution of a poly(catechol borate) and an iridium complex. The alkylation of ammonia and amines with alcohols, alkylating agents, was performed with 1 mol % Ir of the heterogeneous catalyst in water without the use of organic solvents under aerobic conditions to give the corresponding alkylated amines.

Preparation of secondary and tertiary amines from nitroarenes and alcohols

Various secondary amines were obtained selectively from the reaction of nitroarenes with primary alcohols in the presence of ruthenium(ii) complexes having phosphine-amine ligands as the catalyst. Secondary amines could be further alkylated with a primary alcohol using the same catalyst, but different conditions.