23592-67-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 3111, 1987 DOI: 10.1016/S0040-4039(00)96298-1

Upstream product

• 68014-52-8 N-acetyl-2,4,6-trimethyldiphenylamine 
• 622-37-7 Phenyl azide 
• 108-67-8 1,3,5-trimethyl-benzene 
• 23592-65-6 2-(mesitylamino)benzoic acid 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 62-53-3 aniline 
• 108-90-7 chlorobenzene 
• 88-05-1 2,4,6-trimethylaniline 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 14213-00-4 2,4,6-trimethylaniline azide 
• 98-80-6 phenylboronic acid 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 591-50-4 iodobenzene 
• 108-95-2 phenol 

Downstream Products

• 79825-75-5 N-methyl-2,4,6-trimethyldiphenylamine 

Relevant academic research and scientific papers

Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions

Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Herein, we report the implementation of substoichiometric quantities of redox mediators to address limitations to Cu-catalyzed electrosynthesis. Mechanistic studies reveal that mediators serve multiple roles by (i) rapidly oxidizing low-valent Cu intermediates, (ii) stripping Cu metal from the cathode to regenerate the catalyst and reveal the active Pt surface for proton reduction, and (iii) providing anodic overcharge protection to prevent substrate oxidation. This strategy is applied to Chan-Lam coupling of aryl-, heteroaryl-, and alkylamines with arylboronic acids in the absence of chemical oxidants. Couplings under these electrochemical conditions occur with higher yields and shorter reaction times than conventional reactions in air and provide complementary substrate reactivity.

Continuous Synthesis of Aryl Amines from Phenols Utilizing Integrated Packed-Bed Flow Systems

Aryl amines are important pharmaceutical intermediates among other numerous applications. Herein, an environmentally benign route and novel approach to aryl amine synthesis using dehydrative amination of phenols with amines and styrene under continuous-flow conditions was developed. Inexpensive and readily available phenols were efficiently converted into the corresponding aryl amines, with small amounts of easily removable co-products (i.e., H2O and alkanes), in multistep continuous-flow reactors in the presence of heterogeneous Pd catalysts. The high product selectivity and functional-group tolerance of this method allowed aryl amines with diverse functional groups to be selectively obtained in high yields over a continuous operation time of one week.

PHOTOSENSITIVE RESIN COMPOSITION, PHOTOSENSITIVE RESIN LAYER USING THE SAME AND COLOR FILTER

A photosensitive resin composition, a photosensitive resin layer, and a color filter, the composition including a colorant including a first green dye having a core-shell structure and a second green dye in a weight ratio of about 1:9 to about 7:3; a binder resin; a photopolymerizable compound; a photopolymerization initiator; and a solvent.

Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles

Herein, we report a new transition-metal-free robust and cost-effective method for synthesis of 1,2-disubstituted indoles from easily available unactivated (i.e. without EWG, PPh3 or SiR3 groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2-disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N-arylated 2-CF3-indoles. Moreover, this approach can be performed in a one-pot two-step manner directly from commercially available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed.

Facile Buchwald-Hartwig coupling of sterically encumbered substrates effected by PNP ligands

The diphosphinoamine ligands [(Ph2P)2N(Ar); 1 (Ar = C6H5), 2 (Ar = 2,6-iPr2C6H3)] were effectively utilized in Buchwald-Hartwig coupling of a range of sterically demanding substr

Synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compound

The invention discloses a synthesis method for converting lignin 4-O-5 model compound diaryl ether into a nitrogen-containing compound. According to the synthesis method, a diaryl ether compound andan amine compound are subjected to a heating reaction in a certain amount of a solvent (containing a certain amount of water) in an argon atmosphere (containing a certain amount of air) under the actions of a metal catalyst and sodium borohydride, such that the drug with the important physiological activity or the compound with the natural product skeleton containing nitrogen is formed by directlycoupling the C-O bond cut and the amine compound cross while the corresponding aromatic hydrocarbon is obtained. According to the present invention, the synthesis method has characteristics of simpleand easily-available raw materials, high conversion rate, important product and good yield, and has broad application prospects in the degradation and deep development and utilization of lignin.

COLORING COMPOSITION, INK JET INK, AND TEXTILE PRINTING METHOD

Provided are a coloring composition including a compound represented by any one of Formulae (1) to (3) shown in the specification, an ink jet ink including the coloring composition, and a textile printing method.

Synergistic Ligand Effect between N-Heterocyclic Carbene (NHC) and Bicyclic Phosphoramidite (Briphos) Ligands in Pd-Catalyzed Amination

A synergistic ligand effect between NHC and phosphorus ligands in Pd-catalyzed Buchwald-Hartwig amination reactions was demonstrated with tunable π-acceptor bicyclic bridgehead phosphoramidite (briphos) ligands. The catalytic activity of NHC-Pd-L (L = phosphorus ligand) precatalysts depends on the electronic properties of L. A NHC-Pd-L catalyst with an N-cyclohexyl-substituted briphos ligand was found to be highly efficient. A series of C-N bond coupling reactions between primary or secondary amines and aryl chlorides were performed with high yields under mild reaction conditions.

Nickel Dual Photoredox Catalysis for the Synthesis of Aryl Amines

In this work, a new dual photoredox nickel catalysis system has been utilized for the synthesize of aryl amines. Previously, our group has shown that a nickel catalyst in conjunction with a photosensitizer and a sacrificial electron donor can cross-couple C-C bonds via photoredox-assisted reductive coupling. Here we have built upon that system to develop a redox-neutral cross-coupling system for the formation of C-N bonds. The catalytic system is composed of just a nickel cross-coupling catalyst, a Ru photocatalyst, and base and is capable of coupling amines with aryl halides in good to excellent yields. Furthermore, it was found that these reactions are functional under ambient conditions with catalyst loadings of 1 mol %. Spectroscopic studies provide support that this amination mechanism proceeds via a nitrogen-based radical intermediate. This N-radical mechanism offers direct synthetic access to di- and triaryl amines from nickel photocatalysis.

Palladium-Catalyzed Formal Cross-Coupling of Diaryl Ethers with Amines: Slicing the 4-O-5 Linkage in Lignin Models

Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (α-O-4, β-O-4, and 4-O-5 linkages) and other C?C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)?O bond cleavages form valuable nitrogen-containing derivatives.