94533-51-4

Upstream product

• 13880-55-2 N,N,N',N'-tetramethyl-C-phenylmethanediamine 
• 100-52-7 benzaldehyde 
• 124-40-3 dimethyl amine 
• 109-89-7 diethylamine 
• 52853-20-0 benzylidene dimethyl ammonium chloride 
• 103-83-3 N,N'-dimethylbenzylamine 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 50-00-0 formaldehyd 
• 951-87-1 (+)-stilbenediamine 
• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 611-74-5 N,N-dimethylbenzamide 
• 623-26-7 terephthalonitrile 
• 97-94-9 triethyl borane 

Downstream Products

• 103-83-3 N,N'-dimethylbenzylamine 
• 100-52-7 benzaldehyde 
• 622-29-7 N-Benzylidenemethylamine 

Relevant academic research and scientific papers

Dual-Role Catalysis by Thiobenzoic Acid in Cα-H Arylation under Photoirradiation

Thiobenzoic acid (TBA) can serve as a single-electron reducing agent under photoirradiation from a blue light-emitting diode, in the presence of appropriate electron acceptors, and the resulting sulfur-centered radical species undergoes hydrogen atom abstraction. This dual-role catalysis by TBA enables regioselectivie Cα-H arylation of benzylamines, benzyl alcohols, and ethers, as well as dihydroimidazoles, with cyano(hetero)arenes in good yield, without the need for a transition-metal photocatalyst and/or synthetically elaborated organic dyes.

Oxidative and Redox-Neutral Approaches to Symmetrical Diamines and Diols by Single Electron Transfer/Hydrogen Atom Transfer Synergistic Catalysis

Homocoupling reactions of benzylamines and benzyl alcohols were examined under synergistic catalysis conditions with a photoredox catalyst and thiobenzoic acid as a hydrogen atom abstractor. When pivalaldehyde was used as an electron acceptor, oxidative dimerization proceeded selectively, whereas the use of benzaldehydes or iminium ions as electron acceptors resulted in redox-neutral coupling. These reactions afforded symmetrical 1,2-diamines and 1,2-diols in good yields.

Visible light mediated homo- and heterocoupling of benzyl alcohols and benzyl amines on polycrystalline cadmium sulfide

The oxidative coupling of sp3 hybridized carbon atoms by photocatalysis is a valuable synthetic method as stoichiometric oxidation reagents can be avoided and dihydrogen is the only byproduct of the reaction. Cadmium sulfide, a readily available semiconductor, was used as a visible light heterogeneous photocatalyst for the oxidative coupling of benzyl alcohols and benzyl amines by irradiation with blue light. Depending on the structure of the starting material, good to excellent yields of homocoupling products were obtained as mixtures of diastereomers. Cross-coupling between benzyl alcohols and benzyl amines gave product mixtures, but was selective for the coupling of tetrahydroisoquinolines to nitromethane. The results demonstrate that CdS is a suitable visible light photocatalyst for oxidative bond formation under anaerobic conditions.

Reductive coupling of aromatic N,N-acetals using zinc and chlorotrimethylsilane

The reductive coupling of aromatic N,N-acetals and N,O-acetal activated by chlorotrimethylsilane proceeded smoothly in the presence of zinc to give the corresponding diamines in good yields.

Radical fixation of functionalized carbon resources: α-sp 3C - H carbamoylation of tertiary amines with aryl isocyanates

A new carbamoylation of tertiary amines is reported. This rare C - H transformation features the direct generation of α-aminoalkyl radicals from tertiary amines, followed by the addition of the resultant nucleophilic radicals to isocyanates, enabling unique access to N,N-dialkylated amino acid derivatives. The authors put forward a mechanistic proposal that is based on the isolation of borinamides produced by capturing nitrogen radical intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.

Formation of meso-1,2-bis(dimethylamino)-1,2-diphenylethane by oxidative C-C coupling reaction

The title compound was obtained from the reaction of N,N- dimethylbenzylamine with n-butyl lithium and sulfur in tetrahydrofuran at room temperature. Its molecular structure was investigated by means of single crystal X-ray diffraction and quantum chemica

Titanocene-catalyzed coupling of aromatic amides in the presence of organosilanes: A novel route to vicinal diamines and a new class of amine-substituted oligomers

The title reaction has been surveyed for a number of substrates with differing substitution patterns. With a few exceptions, the methodology provides a one-pot synthesis of the 1,2-diamines from widely available and inexpensive starting materials, and in high yields. In addition, the coupling of 1,4-and 1,3-bis-(N,N,N′,N′-tetraalkyl)arylenediamides is shown, under the same experimental conditions, to yield oligomers: R2NC(O)C 6H4CH(NR2)-[CH(NR2)C 6H4CH(NR2)]n-CH(NR 2)C6H4C(O)-NR2 (R = methyl and ethyl; n = 0 to ca. 5). The chemical structures of these unprecedented oligomers are determined by comparison of NMR and MS spectra to those of vicinal diamines, prepared from the analogous N,N-dialkylbenzamides. The origin of the limitation of oligomer chain length is probably due to a specific effect of the internal benzylic amine group, since the substrate 4-Me2NCH 2C6H4C(O)NMe2 was found to be uniquely unreactive compared to the other 4-substituted N,N-dialkylbenzamides investigated. N-Methylphthalimide was briefly studied as a monomer and analysis by MS showed that oligomers are formed. Attempts to fully characterize these polymers were unsuccessful.

Iminopinacol coupling with lithium: Electron-transfer mediators

The addition of tert-butyl borate or ethyl formate to N-alkylbenzalimines directs the reaction pathway from the Birch reduction to the pinacol-type coupling with lithium in THF; an analogous reaction with a dimethylimmonium salt requires a trace titanium catalyst as the electron-transfer mediator.

Use of Carboxylic Acids as Chiral Solvating Agents for the Determination of Optical Purity of Chiral Amines by NMR Spectroscopy

Optically pure mandelic acid, Mosher's acid, and N-(3,5-dinitrobenzoyl)phenylglycine have been used as chiral solvating agents to induce nonequivalence in the 1H NMR spectra of several diamines, amino acid esters, amino alcohols, and other amines.The identity of the chiral solvating agent and the stoichiometry of the solvation complexes that yield the greatest nonequivalence varies with the nature of the substrate.