24215-01-8

Upstream product

• 119-61-9 benzophenone 
• 106-49-0 p-toluidine 
• 2051-90-3 Dichlorodiphenylmethane 
• 53060-12-1 diphenyl-p-tolylmethylamine 
• 21160-02-1 benzophenone O-acetyl oxime 
• 5720-05-8 4-methylphenylboronic acid 
• 1013-88-3 Benzophenone imine 
• 106-43-4 para-chlorotoluene 
• 62-53-3 aniline 
• 78602-55-8 (E)-(4-methylphenyl)methanethial S-oxide 
• 622-58-2 p-Tolylisocyanate 
• 3085-54-9 N-(4-methylphenyl)formamide 
• 7175-47-5 4-methylphenyl isocyanide 
• 595-89-1 Tetraphenyllead 

Downstream Products

• 119-61-9 benzophenone 
• 106-49-0 p-toluidine 
• 1350477-39-2 C₂₁H₁₈N₂ 
• 5110-46-3 2-chloro-2,2-diphenyl-N-p-tolyl-acetimidoyl chloride 
• 76056-06-9 4-methyl-N-diphenylmethylaniline 

Relevant academic research and scientific papers

High turnover number and rapid, room-temperature amination of chloroarenes using saturated carbene ligands

Pd(dba)2, 0.02-2 mol% Ligand 1, 0.08-2 mol% ArCl + NHRR′ → Ar-NRR′ NaO-t Bu, DME Ar = unactivated aryl, rt-100°C (71%-quant.) heteroaryl NHRR′ = 1° and 2° aryl; 2° acyclic and cyclic alkyl; imino A catalytic system for the mild amination of aryl chlorides is described. This system consists of a Pd(0) precursor and a dihydroimidazoline carbene ligand, which is generated in situ from its protonated tetrafluoroborate salt (2). Using this catalyst, aryl and heteroaryl chlorides react with secondary amines and anilines within hours at room temperature. Turnover numbers as high as 5000 are obtained at elevated temperatures for reaction of morpholine with an unactivated aryl chloride.

Copper-Catalysed Electrophilic Amination of Aryl(alkenyl) Boronic Acids with Nitrogen-Containing Hypervalent Iodine (III) Reagent

A copper-catalysed electrophilic N-imination of aryl(alkenyl) boronic acids with a stable hypervalent iodine(III) reagent containing a transferable (diarylmethylene)amino group is developed. The electrophilic C?N cross-coupling reaction proceeds smoothly at room temperature under oxidant-free and base-free conditions, which is further characterized by the broad functional group compatibility, thereof, extending the N-electrophile scope of electrophilic C?N cross-coupling outside the limitation of N?O and N?Cl reagents. (Figure presented.).

An expedient one-pot synthesis of benzophenone Schiff bases from benzene

A simple and efficient one-pot synthesis of benzophenone Schiff bases from benzene, CCl4 and aromatic amines was developed based on the the reaction of benzene with CCl4·AlCl3 complex. This method affords Ph2CCl2 as well as the products of its subsequent reaction with aromatic amines, benzophenone Schiff bases, selectively and in good yields.

Catalytic Imido-Transfer Reactions of Well-Defined Silica-Supported Titanium Imido Complexes Prepared via Surface Organometallic Chemistry

We expand the series of well-defined silica-supported titanium imido complexes of general formula (SiO)Ti(═NtBu)X(py)n prepared via surface organometallic chemistry in order to analyze the effect of the X ligand on their catalytic properties. Two new surface complexes, (SiO)Ti(═NtBu)Cl(py)2 (2s) and (SiO)Ti(═NtBu)Cp(py) (3s), have been prepared and characterized with physicochemical techniques, and their performance in oxo/imido heterometathesis and other catalytic imido-transfer reactions has been studied and compared to that of the previously reported catalyst (SiO)Ti(═NtBu)(Me2Pyr)(py)2 (1s; Me2Pyr = 2,5-dimethylpyrrolyl).

Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines

Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)2 or Pd(PPh3)4 to afford imines and/or α-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas α-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/α-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or α-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.

Oxidative Rearrangement of Primary Amines Using PhI(OAc)2 and Cs2CO3

An oxidative rearrangement of primary amines mediated by a hypervalent iodine(III) reagent is herein reported. The combination of PhI(OAc)2 and Cs2CO3 proves highly efficient at inducing the direct 1,2-C to N migration of primary amines, which can be applied to the preparation of both acyclic and cyclic amines. A mechanistic study shows that the rearrangement proceeds via a concerted mechanism.

Photocatalytic and Chemoselective Transfer Hydrogenation of Diarylimines in Batch and Continuous Flow

A visible-light photocalytic method for the chemoselective transfer hydrogenation of imines in batch and continuous flow is described. The reaction utilizes Et3N as both hydrogen source and single-electron donor, enabling the selective reduction of imines derived from diarylketimines containing other reducible functional groups including nitriles, halides, esters, and ketones. The dual role of Et3N was confirmed by fluorescence quenching measurements, transient absorption spectroscopy, and deuterium-labeling studies. Continuous-flow processing facilitates straightforward scale-up of the reaction.

Catalytic Oxo/Imido Heterometathesis by a Well-Defined Silica-Supported Titanium Imido Complex

Grafting Ti(=NtBu)(Me2Pyr)2(py)2 (Me2Pyr= 2,5-dimethylpyrrolyl, py=pyridine) onto the surface of silica partially dehydroxylated at 700 °C gives the well-defined silica-supported Ti imido complex (≡SiO)Ti(=NtBu)(Me2Pyr)(py)2, which is fully characterized by IR and solid-state NMR spectroscopy as well as elemental and mass balance analyses. While stoichiometric imido-transfer reactivity is typical for Ti imides, the obtained surface complex is unique in that it enables catalytic transformations involving Ti imido and oxo intermediates. In particular, it efficiently catalyzes imidation of carbonyl compounds with N-sulfinylamines by oxo/imido heterometathesis.

Generation and selected reactions of chlorinated thiocarbonyl S-imides*

N-Aryl-1,1,1-trichloromethanesulfenamides ArNH-SCCl3 easily undergo dehydrochlorination upon treatment with potassium hydroxide in ethanolic solution. The intermediate thiocarbonyl S-imides formed thereby behave differently depending on the typ

An Air-Stable Nickel(0) Phosphite Precatalyst for Primary Alkylamine C-N Cross-Coupling Reactions

In this report we describe the design and preparation of a new air-stable nickel phosphite based catalyst for unique C-N bond forming processes. Specifically, (BINAP)Ni[P(OPh)3]2, is presented as an effective catalyst for a range of amination reactions between aryl halides and primary alkylamines. The results are supported by relevant kinetic studies, DFT calculations and a catalytic cycle indicating possible reaction intermediates. The amination reaction between a series of aryl halides and primary alkylamines is described using a new air-stable nickel phosphite based catalyst (BINAP)Ni[P(OPh)3]2.