42834-19-5

Upstream product

• 119-61-9 benzophenone 
• 104-94-9 4-methoxy-aniline 
• 100306-02-3 N-(4-hydroxyphenyl)benzophenone imine 
• 77-78-1 dimethyl sulfate 
• 1013-88-3 Benzophenone imine 
• 623-12-1 4-chloromethoxybenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 2051-90-3 Dichlorodiphenylmethane 
• 10349-38-9 p-methoxyphenylisonitrile 
• 595-89-1 Tetraphenyllead 
• 5470-34-8 4-methoxyformanilide 
• 53060-13-2 p-anisyldiphenylmethylamine 
• 4181-97-9 phenyl 4-methoxybenzoate 
• 114583-47-0 benzophenone N,N,N-trimethylhydrazonium iodide 

Downstream Products

• 6709-42-8 N-(4-methoxyphenyl)-1,1-diphenylmethylamine 
• 104-94-9 4-methoxy-aniline 
• 1569314-23-3 2-(4-methoxyphenyl)-1-phenyl-3,4-di-p-tolylisoquinolin-2-ium tetrafluoroborate 
• 114792-63-1 N-benzhydryl-N-(4-methoxy-phenyl)-N'-phenyl-urea 
• 102459-38-1 acetic acid-(N-benzhydryl-p-anisidide) 
• 1202914-01-9 2,2-diphenyl-2-(N-4-methoxyphenylamino)acetonitrile 

Relevant academic research and scientific papers

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.

A Convenient Preparation Method for Benzophenone Imine Catalyzed by Tetrabutylammonium Fluoride

Benzophenone imine is a useful ammonia equivalent in the Buchwald-Hartwig amination and an important intermediate for the synthesis of N-protected primary amines. However, the conventional synthesis of benzophenone imine requires stoichiometric amounts of metal reagents or high-pressure conditions. Herein we report a facile method for preparing benzophenone imine to enhance its potential utility. The reaction is performed by mixing commercially available benzophenone and bis(trimethylsilyl)amine in the presence of a catalytic amount of tetrabutylammonium fluoride at ambient temperature and pressure and can be readily applied to a multigram-scale synthesis even in a standard academic laboratory setup. Preliminary mechanistic studies and the application of the reaction to one-pot benzophenone imine synthesis/Buchwald-Hartwig amination are also reported.

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.

Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water

A novel carbanionic reactivity of imines mediated by photoredox catalysis is demonstrated. The umpolung imine reactivity is exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines (up to 98% yield). Deuterium is introduced into amines efficiently using D2O as an inexpensive deuterium source (≥95% D ratio). The mechanism of this unusual transformation is probed.

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.

Efficient Synthesis of Amines by Iron-Catalyzed C=N Transfer Hydrogenation and C=O Reductive Amination

Here we report the catalytic transfer hydrogenation (CTH) of non-activated imines promoted by a Fe-catalyst in the absence of Lewis acid co-catalysts. Use of the (cyclopentadienone)iron complex 1, which is much more active than the classical ‘Kn?lker complex’ 2, allowed to reduce a number of N-aryl and N-alkyl imines in very good yields using iPrOH as hydrogen source. The reaction proceeds with relatively low catalyst loading (0.5–2 mol%) and, remarkably, its scope includes also ketimines, whose reduction with a Fe-complex as the only catalyst has little precedents. Based on this methodology, we developed a one-pot CTH protocol for the reductive amination of aldehydes/ketones, which provides access to secondary amines in high yield without the need to isolate imine intermediates. (Figure presented.).

Manganese-Catalyzed C?H Annulation of Ketimines with Allenes: Stereoselective Synthesis of 1-Aminoindanes

A manganese-catalyzed C?H annulation of ketimines with poly-substituted ester-activated allenes toward the synthesis of 1-aminoindanes bearing two vicinal all-substituted carbon stereocenters and an exocyclic double bond was developed. The reaction featur

Catalytic Ester and Amide to Amine Interconversion: Nickel-Catalyzed Decarbonylative Amination of Esters and Amides by C?O and C?C Bond Activation

An efficient nickel-catalyzed decarbonylative amination reaction of aryl and heteroaryl esters has been achieved for the first time. The new amination protocol allows the direct interconversion of esters and amides into the corresponding amines and represents a good alternative to classical rearrangements as well as cross coupling reactions.