5877-55-4

Usage

InChI:InChI=1/C14H13N/c1-12-7-5-6-10-14(12)15-11-13-8-3-2-4-9-13/h2-11H,1H3

Upstream product

• 100-52-7 benzaldehyde 
• 95-53-4 o-toluidine 
• 92-29-5 hydrobenzamide 
• 10421-79-1 benzaldehyde o-tolylhydrazone 
• 88-72-2 1-methyl-2-nitrobenzene 
• 108-88-3 toluene 
• 100-51-6 benzyl alcohol 
• 100-46-9 benzylamine 
• 614-77-7 N-(2-methylphenyl)urea 
• 94-41-7 benzalacetophenone 
• 93-58-3 benzoic acid methyl ester 
• 13381-65-2 α-Bromobenzyl benzoate 

Downstream Products

• 609-72-3 N,N-dimethyl-o-toluidine 
• 606-46-2 N,N-diethyl-o-toluidine 
• 5405-13-0 N-benzyl-2-methylaniline 
• 588-64-7 benzaldehyde phenylhydrazone 
• 16552-02-6 α-Cyan-zimtsaeure-o-toluidid 
• 142888-66-2 3-o-tolyl-2-styryl-3,4-dihydro-4-quinazolone 
• 2004-80-0 2-styryl-3-(o-tolyl)quinazolin-4(3H)-one 
• 88252-49-7 (3R,4R)-3-(4-Chloro-phenoxy)-4-phenyl-1-o-tolyl-azetidin-2-one 
• 948-65-2 2-phenyl-indole 
• 100-52-7 benzaldehyde 
• 95-53-4 o-toluidine 
• 108-88-3 toluene 
• 100-47-0 benzonitrile 
• 71-43-2 benzene 

Relevant academic research and scientific papers

Copper-Catalyzed Intramolecular Amination of C(sp3)-H Bond of Secondary Amines to Access Azacycles

The cross-coupling of C-N bond directly from inert C-H bonds is an ideal approach to synthesize saturated azacycles due to its high efficiency and atom economy. In this article, a copper-catalyzed intramolecular amination via the cross coupling of C(sp3)-H and N-H bonds of secondary amine has been reported, which exhibit excellent chemo- and regioselectivity, extensive substrate scope, and functional group tolerance in good to excellent yield, offering an efficient pathway to build nitrogen-containing heterocycle skeletons.

Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles

A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.

One-Pot Synthesis of Schiff Bases by Defect-Induced TiO2- x-Catalyzed Tandem Transformation from Alcohols and Nitro Compounds

Schiff bases that are generally formed from condensation reactions of aldehydes (or ketones) and amino groups could also be produced by a photodriven one-pot tandem reaction between alcohols and nitro compounds, in our case. Herein, TiO2-x porous cages derived from NH2-MIL-125 by a self-sacrificing template route are used to study the organic transformation and exhibit 100% conversion efficiency of nitrobenzene and 100% selectivity for Schiff bases in the system of benzyl alcohol (5 mL) and nitrobenzene (41 μL) upon light irradiation, but hydrogen by dehydrogenation of benzyl alcohol cannot be detected. Successful occurrence of the organic transformation is mainly attributed to Ti(III)-oxygen vacancy associates. Surface oxygen vacancy-related Ti(III) sites are responsible for binding with nitro groups, and low-coordinated Ti5c sites selectively adsorb hydroxyl groups of benzyl alcohol. The Ti(III) and oxygen vacancy associates capture photogenerated electrons for achievement of multielectron reduction of nitrobenzene and the subsequent Schiff base condensation reaction with the as-formed benzaldehyde.

Photocatalytic one-pot multidirectional N-alkylation over Pt/D-TiO2/Ti3C2: Ti3C2-based short-range directional charge transmission

Visible-light-induced one-pot, multistep, and chemoselectivity adjustable reactions highlight the economical, sustainable, and green process. Herein, we report Pt nanoparticles dispersed on S and N co-doped titanium dioxide/titanium carbide (MXene) (3%Pt/

Direct synthesis of imines from nitro compounds and biomass-derived carbonyl compounds over nitrogen-doped carbon material supported Ni nanoparticles

The selective synthesis of imines from biomass-derived chemicals over heterogeneous non-noble metal catalysts is of great importance for organic transformation. Herein, non-noble heterogeneous nitrogen-doped carbon supported Ni catalysts (abbreviated as Ni/CN-MgO-T, whereTrepresents the pyrolysis temperature) have been facilely prepared from the simple pyrolysis of Ni precursors and biomass, and Ni/CN-MgO-600 with the smallest size of Ni nanoparticles demonstrated the highest catalytic activity. The reductive coupling of nitroarenes and carbonyl compounds could be performed under mild conditions (80 °C, and 10 bar H2), affording structurally-diverse imines with high to excellent yields (84.2-98.1%). Thanks to the mild reaction conditions, the developed method showed good tolerance to other functional groups such as nitriles, halogen and vinyl groups.

Highly chemoselective synthesis of imine over Co/Zn bimetallic MOFs derived Co3ZnC-ZnO embed in carbon nanosheet catalyst

One-pot direct synthesis of imines via reductive amination of nitroarenes with aromatic aldehydes remains a great challenge due in part to its over-hydrogenation of imines to secondary amines. Herein, a novel Co3ZnC and ZnO supported on N-doped carbon nanosheet catalyst with the thickness of ca. 5.0 nm was fabricated through the direct pyrolysis of a Co/Zn bimetallic MOFs at 500 °C (named as Co3ZnC-ZnO/NC-500). Surprisingly, the developed Co3ZnC-ZnO/NC-500 catalyst delivers 99.9 % conversion of nitrobenzene and 98.5 % selectivity to N-benzylideneaniline in one-pot reductive amination of nitrobenzene with benzaldehyde. Various characterizations (including as SEM, XRD, TEM, AFM, XPS, Raman and N2 adsorption–desorption) have revealed that the generated small size of Co3ZnC alloy, abundant structural defects, larger specific surface area (105.5 m2·g?1) as well as more basic sites are responsible for the outstanding catalytic activity of Co3ZnC-ZnO/NC-500 catalyst for tandem reaction. Moreover, the Co3ZnC-ZnO/NC-500 catalyst exhibits high stability during the recycling experiments without the loss of its catalytic activity. Notably, the results of contrast experiments have demonstrated that the intentional introduction of ZnO in Co3ZnC-ZnO/NC-500 catalyst plays a key role in the selectivity to N-benzylideneaniline in the tandem reaction. This study provides a new guideline for designing tandem catalysts with high selectivity.

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Efficient Imine Formation by Oxidative Coupling at Low Temperature Catalyzed by High-Surface-Area Mesoporous CeO2 with Exceptional Redox Property

High-surface-area mesoporous CeO2 (hsmCeO2) was prepared by a facile organic-template-induced homogeneous precipitation process and showed excellent catalytic activity in imine synthesis in the absence of base from primary alcohols and amines in air atmosphere at low temperature. For comparison, ordinary CeO2 and hsmCeO2 after different thermal treatments were also investigated. XRD, N2 physisorption, UV-Raman, H2 temperature-programmed reduction, O2 temperature-programmed desorption, EPR spectroscopy, and X-ray photoelectron spectroscopy were used to unravel the structural and redox properties. The hsmCeO2 calcined at 400 °C shows the highest specific surface area (158 m2 g?1), the highest fraction of surface coordinatively unsaturated Ce3+ ions (18.2 %), and the highest concentration of reactive oxygen vacancies (2.4×1015 spins g?1). In the model reaction of oxidative coupling of benzyl alcohol and aniline, such an exceptional redox property of the hsmCeO2 catalyst can boost benzylideneaniline formation (2.75 and 5.55 mmol (Formula presented.) h?1 based on >99 % yield at 60 and 80 °C, respectively) in air with no base additives. It can also work effectively at a temperature of 30 °C and in gram-scale synthesis. These are among the best results for all benchmark ceria catalysts in the literature. Moreover, the hsmCeO2 catalyst shows a wide scope towards primary alcohols and amines with good to excellent yield of imines. The influence of reaction parameters, the reusability of the catalyst, and the reaction mechanism were investigated.

Efficient imine synthesisviaoxidative coupling of alcohols with amines in an air atmosphere using a mesoporous manganese-zirconium solid solution catalyst

Direct oxidative coupling of alcohols with amines using a non-precious metal oxide catalyst under mild conditions is highly desirable for imine synthesis. In this work, a mesoporous Mn1ZrxOysolid solution catalyst prepared by a co-precipitation method showed excellent catalytic performance in imine synthesis from primary alcohols and amines without base additives in an air atmosphere. XRD, N2physisorption, H2-TPR, O2-TPD, EPR and XPS were comprehensively used to unravel its structural, redox and amphoteric properties that closely depended on the interaction between MnOyand ZrO2with a variable Zr ratio. The Mn1Zr0.5Oycatalyst presented the highest fractions of Mn3+ions and reactive oxygen species on the surface, and the highest concentrations of acidic-basic sites, which were disclosed to play important roles in activating alcohols and molecular O2in the rate-determining step. In the model reaction of oxidative coupling of benzyl alcohol with aniline, such enhanced features of the Mn1Zr0.5Oycatalyst can promote the intrinsic catalytic activity (iTOF of 1.87 h?1) and boost benzylideneaniline formation (5.56 mmol gcat.?1h?1) based on a >99% yield at 80 °C respectively at a fast response. It can also work effectively at a room temperature of 30 °C, as well as for the gram-grade synthesis. This is one of the best results among all the MnOy-based catalysts in the literature. Moreover, this catalyst showed good stability and a wide substrate scope with good to excellent yields of imines.

Catalyst- And Solvent-Free Synthesis of α-Amino Polyfluoroalkylphosphonates from Bis(fluoroalkyl) Phosphonates and Aldimines

The catalyst- and solvent-free reaction between bis(fluoroalkyl) phosphonates and aldimines occurs under mild conditions (20-22 °C, 0.25-4 h) to afford a new family of α-amino polyfluoroalkylphosphonates in up to quantitative yields.