3661-49-2

Upstream product

• 53034-26-7 m-Methoxyphenyllead(IV) triacetate 
• 104-94-9 4-methoxy-aniline 
• 58273-38-4 3-(4-methoxy phenylamino)phenol 
• 77-78-1 dimethyl sulfate 
• 555-03-3 3-nitroanisole 
• 5720-07-0 4-methoxyphenylboronic acid 
• 2398-37-0 3-methoxyphenyl bromide 
• 100-17-4 para-methoxynitrobenzene 
• 536-90-3 m-Anisidine 
• 100-66-3 methoxybenzene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 540-38-5 p-Iodophenol 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 109688-74-6 2-methoxy-N⁴-(4-methoxy-phenyl)-p-phenylenediamine 
• 944284-88-2 [(3-methoxyphenyl)-4-methoxyphenylamino]acetonitrile 
• 1573202-44-4 N²,N²,N^2',N^2',N⁷,N⁷,N^7',N^7'-octakis(3-methoxypheny)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine 

Relevant academic research and scientific papers

Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines

The development and study of a simple copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic investigations established that the cross-coupling reaction proceeds via a nitrosoarene intermediate and that copper is required to catalyze both the deoxygenation of the nitroarene to afford the nitrosoarene and C-NAr bond formation of the nitrosoarene with the aryl boronic acid.

Light-Promoted C–N Coupling of Aryl Halides with Nitroarenes

A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald–Hartwig C–N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a NiI/NiIII cycle, to a nitrosoarene intermediate.

A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines

A terphenyl phosphine ligand (2,6-bis(2,4,6-triisopropylphenyl)phenyl-dicyclohexylphosphine, TXPhos) and its supported palladium complex [(TXPhos)(allyl)PdCl] have been developed and the catalyst system is highly efficient in amination of aryl halides with 1° anilines, especially effective for densely functionalized substrates including both partners possessing ortho-ester, acetyl, nitrile and nitro groups. With the TXPhos-supported catalyst system, many partner combinations have been unprecedentedly realized and the base scope has been even extended to KOAc, which is even the best choice in the amination of 2-nitrochlorobenzene.

Dialkylterphenyl Phosphine-Based Palladium Precatalysts for Efficient Aryl Amination of N-Nucleophiles

A series of 2-aminobiphenyl palladacycles supported by dialkylterphenyl phosphines, PR2Ar′ (R=Me, Et, iPr, Cyp (cyclopentyl), Ar′=ArDipp2, ArXyl2f, Dipp (2,6-C6H3-(2,6-C6H3-(CHMe2)2)2), Xyl=xylyl) have been prepared and structurally characterized. Neutral palladacycles were obtained with less bulky terphenyl phosphines (i.e., Me and Et substituents) whereas the largest phosphines provided cationic palladacycles in which the phosphines adopted a bidentate hemilabile k1-P,η1-Carene coordination mode. The influence of the ligand structure on the catalytic performance of these Pd precatalysts was evaluated in aryl amination reactions. Cationic complexes bearing the phosphines PiPr2ArXyl2 and PCyp2ArXyl2 were the most active of the series. These precatalysts have demonstrated a high versatility and efficiency in the coupling of a variety of nitrogen nucleophiles, including secondary amines, alkyl amines, anilines, and indoles, with electronically deactivated and ortho-substituted aryl chlorides at low catalyst loadings (0.25–0.75 mol % Pd) and without excess ligand.

Hole transporting material taking carbazoles bonded with tetracarbon chain as core as well as preparation method and application of hole transporting material

The invention discloses a novel hole transporting material taking carbazoles bonded with a tetracarbon chain as a core as well as a preparation method and application of the novel hole transporting material. The hole transporting material taking carbazole

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.

Synthesis and Photophysical Characterization of 2,3-Dihydroquinolin-4-imines: New Fluorophores with Color-Tailored Emission

In this study, a series of variously substituted 2,3-dihydroquinolin-4-imines (DQIs) were synthesized from N-substituted propargylanilines by copper(I)-catalyzed annulation. The approach adopted in this study under mild, effective conditions exhibited broad substrate tolerance, particularly for functional groups substituted on anilines. Most of the DQI derivatives synthesized under optimal conditions were obtained in good isolated yields of 63–88 %. 2,3-Dihydroquinolinimine thus obtained was easily converted to important structures like 2,3-dihydroquinolone and tetrahydrobenzodiazepin-5-one, confirming the importance of this strategy in constructing various heterocycles. Surprisingly, 2,3-dihydroquinolinimines thus obtained exhibited bright fluorescence with quantum yields up to 66 %. The density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were performed for understanding the excited-state nature of DQI system. Accordingly, a tailored DQI derivative bearing methoxy group at C-6 position and acetoxy group at C-7 position was designed and synthesized to give emission at 559 nm with redshift compared to the 7-methoxy substituted DQI. A detailed study of DQI structures with their photophysical properties was performed with five control molecules and consequently demonstrated the uniqueness of the chemical structures of DQIs.

A new kind of a hole transporting material and its preparation method and application

The invention discloses a novel hole transport material, and a preparation method and application thereof. The structural formula of the novel hole transport material is disclosed as Formula (I), wherein R1-R28 are respectively hydrogen (H) or methoxy gro

Molecular engineering of the hole-transporting material spiro-OMeTAD: Via manipulation of alkyl groups

Aliphatic substituent effects on the HOMO energy levels and the ability to transport charge and form stable molecular glasses of systematically modified spiro-OMeTAD analogues were investigated. It was determined that the thermal properties, energy levels and hole mobility values are dependent on the number of alkyl substituents and their position in the investigated spirobifluorene-based hole transporting materials (HTMs). The charge mobility of HTM3 possessing a seemingly insignificant m-methyl group in the diphenylamino moieties is the highest with a value of 2.8 × 10-3cm2V-1s-1at 6.4 × 105V cm-1field strength. It was found that moving one methoxy group into the m-position in the diphenylamino fragment ensured a stable amorphous phase of HTM1. Moreover, the long-term stability of a solid state dye-sensitized solar cell (ssDSSC) device comprising HTM1 was significantly enhanced over a cell with spiro-OMeTAD, in lifetime tests. The findings described in this publication could be applicable to hybrid solar cell research as a number of well-performing architectures rely heavily upon doped spiro-OMeTAD as a HTM.

Thermally Induced Denitrogenative Annulation for the Synthesis of Dihydroquinolinimines and Chroman-4-imines

A rapid growth in synthetic methods for the preparation of diverse organic molecules using N-sulfonyl-1,2,3-triazoles is of great interest in organic synthesis. Transition metals are generally used to activate the α-imino diazo intermediates. Metal-free methods have not been studied in detail, but can be a good complement to transition metal catalysis in the mild reaction conditions. We herein report a novel method for the preparation of 2,3-dihydroquinolin-4-imine and chroman-4-imine analogs from their corresponding N-sulfonyl-1,2,3-triazoles in the absence of metal catalysts. To achieve intramolecular annulation, the introduction of an electron-donating group is required at the meta position of N-sulfonyl-1,2,3-triazole methyl anilines. The inclusion of tailored substituents on the aniline moieties and nitrogen atoms enhances the nucleophilicity of the phenyl π-electrons, thus allowing them to undergo a Friedel-Crafts-type reaction with the highly electrophilic ketenimines. This metal-free method was carefully optimized to generate a variety of dihydroquinolin-4-imines and chroman-4-imines in moderate-to-good yields.