56644-01-0

Upstream product

• 2272-45-9 benzal-p-toluidine 
• 1613-92-9 (E)-N-benzylidene-4-toluidine 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 27549-67-3 dl-N,N'-bis(4-methylphenyl)-1,2-diphenyl-1,4-ethanediamine 
• 34143-86-7 N-((E)-benzylidene)-o-toluidine 
• 2362-77-8 (4-methylbenzylidene)phenylamine 

Downstream Products

• 134-81-6 benzil 
• 1613-92-9 (E)-N-benzylidene-4-toluidine 
• 27549-67-3 (+)-N,N'-di-p-tolyl-bibenzyl-α,α'-diyldiamine 

Relevant academic research and scientific papers

Reductive self-coupling reaction of imines and aldehydes induced by strontium metal

Aromatic aldimines reacted with Sr in the presence of a catalytic amount of iodine to give self-coupling products in good yields, whereas aromatic and aliphatic aldehydes underwent a similar reaction effected by the combined use of Sr and Al(OEt)3. Copyright

Indium-catalyzed reductive coupling of aromatic carbonyl compounds and imines in the presence of aluminum and chlorosilanes

Reductive homocoupling of aromatic aldehydes, ketones, and imines has been achieved in tetrahydrofuran (THF) at room temperature using a catalytic amount of InCl3 (0.5-3.0 mol %) under a nitrogen atmosphere in the presence of chlorotrimethylsilane (TMSCl) and aluminum metal (Al) to provide the corresponding 1,2-diols and 1,2-diamines, respectively, in good to moderate yields. Other indium compounds such as In(NO3)3, cyclopentadienylindium, and indium metal have also been revealed to be effective as catalysts. The catalytic effect of the indium compound is remarkable, and, thus, without it, no reaction occurs in the case of aromatic aldehydes and aldimines, and an induction period is quite long in the case of aromatic ketones. Without either TMSCl or Al, no reaction proceeds even in the presence of the catalyst. Unfortunately, the diastereoselectivity of the products (dl and meso) is not high. Although the precise reaction scheme is not yet clear, we tentatively propose that a redox-active In-Al alloy might be formed on the surface of aluminum in the presence of TMSCl, and an electron transfer from the alloy to substrate might occur.

Organic reaction in water. Part 1. A convenient method for reduction of imines using zinc powder

Reduction of imines was performed with zinc powder in 5% aqNaOH solution without any organic solvents under mild conditions, and the corresponding amines were obtained in good yields.

Novel reductive coupling of aldimines to vicinal diamines

Reductive coupling of aldimines into vicinal diamines has been performed by the action of aluminium/bismuth powder and potassium hydroxide in methanol at ambient temperature in high yields.

Reductive dimerization of anils and regeneration of ketone from oximes and hydrazones by zinc dust and ammonium chloride

Treatment of benzylideneanilines 1a-e with zinc dust and ammonium chloride gives the corresponding diamines 2a-e.A mixture of dl- and meso isomers is obtained in the case of benzylideneaniline 1a.Benzophenone is obtained quantitatively, when benzophenone

Samarium Diiodide-Promoted Reductive Coupling of Imines

Aromatic aldimines are reductively coupled to 1,2-diamines by treatment with samarium diiodide.Cross-coupling of aromatic ketimines with ketones to 2-aminoalcohols is also promoted by the same reagent.

Electrosynthesis of N-Substituted DL-Arylglycineesters and 1,2-Diarylamino-1,2-diarylethanes by Cathodic Reduction of Azomethines in the Presence of Carbon Dioxide

The electroreduction of the N-arylidene-arylamines 1-12 in CO2-saturated solvents of low proton availability as DMF at markedly more positive potentials than carbon dioxide end up in carboxylating the C-atom and hydrogenating the nitrogen of the C=N-double bond.The resulting N-arylsubstituted DL-arylglycines and traces of carbamates may be isolated as esters, adding ethylchloride during the electrolysis.A competing pathway of the electrocarboxylation is the C-C-hydrodimerisation and the hydrogenation of the C=N-double bond, whose importance increases with the water content of the solvent.Based on cyclic-voltametric evidence and product analysis the mechanism of the reductive electrocarboxylation reaction is discussed in terms of nucleophilic attack of the azomethine anion radical on a proton or CO2.