2879-66-5

Upstream product

• 4553-59-7 2-anilino-2-phenylacetonitrile 
• 925-90-6 ethylmagnesium bromide 
• 67-56-1 methanol 
• 139212-76-3 methyl trans-3-(p-methoxyphenyl)-5-(trans-1,3,4,5-tetraphenylperhydro-2-imidazolyl)-2-isoxazoline-4-carboxylate 
• 75-77-4 chloro-trimethyl-silane 
• 538-51-2 benzylidene phenylamine 
• 75-00-3 chloroethane 
• 124-38-9 carbon dioxide 
• 95-14-7 1,2,3-Benzotriazole 
• 91-01-0 1,1-Diphenylmethanol 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 74-96-4 ethyl bromide 
• 100-52-7 benzaldehyde 
• 151257-56-6 1,2-Bis-benzotriazol-1-yl-N,N'-diphenyl-ethane-1,2-diamine 

Downstream Products

• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 2879-66-5 (+)-N,N'-diphenyl-bibenzyl-α,α'-diyldiamine 
• 135075-62-6 (4RS,5RS)-(E)-3-(1,3,4,5-Tetraphenylimidazolidin-2-yl)propenoate 
• 135075-66-0 (2S,3S,4S,5R)-5-Phenyl-3-((4S,5S)-1,3,4,5-tetraphenyl-imidazolidin-2-yl)-pyrrolidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester 
• 135075-66-0 (2S,3S,4S,5R)-5-Phenyl-3-((4R,5R)-1,3,4,5-tetraphenyl-imidazolidin-2-yl)-pyrrolidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester 
• 60644-40-8 (4S,5S)-1,3,4,5-Tetraphenyl-imidazolidine 
• 60644-40-8 1,3-cis-4,5-Tetraphenyl-imidazolidin 

Relevant academic research and scientific papers

A Metal-Free Approach to 1,2-Diamines via Visible Light-Driven Reductive Coupling of Imines with Perylene as a Photoredox Catalyst

A simple, metal-free, and versatile approach to 1,2-diamines has been developed based on reductive coupling reactions of various imines, where perylene, an aromatic hydrocarbon, was used as a photoredox catalyst under visible light irradiation using a white light-emitting diode. The use of 1 mol % perylene enabled almost complete conversion of the imines, leading to the formation of their corresponding 1,2-diamines, which were isolated in good yields. The ratios between dl and meso diamines ranged from 31:69 to 82:18 depending on the substituents of the imines.

A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the Synthesis of Cis -Vicinal Diamines

A highly stereoselective metal-free hydrogenation of vicinal diimines has been successfully realized for the first time using 5-10 mol % of Piers borane as a catalyst under mild conditions, and a variety of cis-1,2-diamines were obtained in 92-99% yields.

Titanium promoted reduction of imines with Grignards, silanes, and zinc: Identification of a new mechanism with silanes

Aldimines react with reducing agents, such as Grignards, phenylsilane or zinc in the presence of titanium(IV) isopropoxide to form amines and reductively coupled imines (diamines). Using deuterium labeled reagents, the mechanism of reduction to form amine

Use of electrochemistry to provide efficient SmI2 catalytic system for coupling reactions.

Samarium metal has been used for the first time as electrode material to perform as an efficient and versatile SmI2 catalytic system assisted by electrochemistry. The established electrocatalytic procedure that excludes any metal additives was successfully applied in various transformations mediated by this useful reagent.

Computational tools for mechanistic discrimination in the reductive and metathesis coupling reactions mediated by titanium(IV) isopropoxide

A theoretical study has been carried out at the B3LYP/LANL2DZ level to compare the reactivity of phenyl isocyanate and phenyl isothiocyanate towards titanium(IV) alkoxides. Isocyanates are shown to favour both mono insertion and double insertion reactions. Double insertion in a head-to-tail fashion is shown to be more exothermic than double insertion in a head-to-head fashion. The head-to-head double insertion leads to the metathesis product, a carbodiimide, after the extrusion of carbon dioxide. In the case of phenyl isothiocyanate, calculations favour the formation of only mono insertion products. Formation of a double insertion product is highly unfavourable. Further, these studies indicate that the reverse reaction involving the metathesis of N,N ′-diphenyl carbodiimide with carbon dioxide is likely to proceed more efficiently than the metathesis reaction with carbon disulphide. This is in excellent agreement with experimental results as metathesis with carbon disulphide fails to occur. In a second study, multilayer MM/QM calculations are carried out on intermediates generated from reduction of titanium(IV) alkoxides to investigate the effect of alkoxy bridging on the reactivity of multinuclear Ti species. Bimolecular coupling of imines initiated by Ti(III) species leads to a mixture of diastereomers and not diastereoselective coupling of the imine. However if the reaction is carried out by a trimeric biradical species, diastereoselective coupling of the imine is predicted. The presence of alkoxy bridges greatly favours the formation of the d,l (±) isomer, whereas the intermediate without alkoxy bridges favours the more stable meso isomer. As a bridged trimeric species, stabilized by bridging alkoxy groups, correctly explains the diastereoselective reaction, it is the most likely intermediate in the reaction.

A samarium "soluble" anode: A new source of SmI2 reagent for electrosynthetic application

An electrochemical method to prepare solutions of samarium diiodide in THF is reported. The simple electrolysis of a samarium rod provides a rapid and straightforward in situ synthesis of SmI2. The electrogenerated complex catalyzes various C-C bond formations. The reagent is produced continuously (see scheme) and leads to efficient organic electrosynthesis with significantly smaller amounts of solvent than usually required. Copyright

Autocatalysis and surface catalysis in the reduction of imines by SmI 2

The reduction of the three imines, N-benzylidene aniline (BAI), N-benzylidenemethylamine (BMI), and benzophenone imine (BPI), with SmI 2 gives the reduced as well as coupled products. The reactions were found to be autocatalytic due to the formation of the trivalent samarium in the course of the reaction. When preprepared SmI3 was added to the reaction mixture, the reaction rate increased significantly. However, the kinetics were found to be of zero order in SmI2. This type of behavior is typical of surface catalysis with saturation of the catalytic sites. Although no solids are visible to the naked eye, the existence of microcrystals was proven by light microscopy as well as by dynamic light scattering analysis. Although HRTEM shows the existence of quantum dots in the solid, we were unable to make a direct connection between the existence of the quantum dots and the catalytic phenomenon. In the uncatalyzed reaction, the order of reactivity is BPI > BMI > BAI. This order does not conform to the electron affinity order of the substrates but rather to the nitrogen lone pair accessibility for complexation. This conclusion was further supported by using HMPA as a diagnostic probe for the existence of an inner sphere electron transfer reaction.

Diastereospecific coupling of imines by low-valent titanium: An experimental and Computational study

The reaction of phenylsilane (PhSiH3) and titanium(IV) isopropoxide [Ti(OiPr)4] generates low-valent titanium alkoxides that reduce and reductively couple imines. The C-C coupling reaction is diastereospecific, with exclusive formati

Homocoupling of aldimines mediated by zirconocene: Synthesis of vicinal diamines and imidazolidines

The reductive coupling of imines in the presence of the lanthanide-originated zirconocene equivalent allows the synthesis of vicinal diamines or imidazolidines under mild conditions in good yields with high diastereoselectivity.

A new Yb3+-catalyzed pinacol and imine-coupling reaction

Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.