17273-16-4

Upstream product

• 119-61-9 benzophenone 
• 106-47-8 4-chloro-aniline 
• 106-39-8 bromochlorobenzene 
• 1013-88-3 Benzophenone imine 
• 26456-05-3 10-methylacridinium perchlorate 
• 53060-10-9 4-chloro-tritylamine 
• 1885-81-0 p-chlorophenyl isocyanide 
• 595-89-1 Tetraphenyllead 
• 2617-79-0 N-(4-chlorophenyl)formamide 
• 2051-90-3 Dichlorodiphenylmethane 
• 1679-18-1 4-Chlorophenylboronic acid 

Downstream Products

• 101868-35-3 N‐(diphenylmethyl)‐4‐chloroaniline 
• 106-47-8 4-chloro-aniline 

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.

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.

Facile synthesis of triarylmethanimine promoted by a lewis acidbase pair: Theoretical and experimental studies

An efficient method for triarylmethanimine synthesis promoted by a Lewis acidbase pair (AlCl3Et3N) was designed using mechanistic analysis with the aid of density functional theory. A series of triarylmethanimines were successfully prepared under mild con

Hydride, hydrogen, proton, and electron affinities of imines and their reaction intermediates in acetonitrile and construction of thermodynamic characteristic graphs (TCGs) of imines as a molecule ID card

(Chemical Equation Presented) A series of 61 imines with various typical structures were synthesized, and the thermodynamic affinities (defined as enthalpy changes or redox potentials in this work) of the imines to abstract hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the imines to abstract hydrogen atoms and protons, and the thermodynamic affinities of the hydrogen adducts of the imines to abstract electrons in acetonitrile were determined by using titration calorimetry and electrochemical methods. The pure heterolytic and homolytic dissociation energies of the C=N π-bond in the imines were estimated. The polarity of the C=N double bond in the imines was examined using a linear free-energy relationship. The idea of a thermodynamic characteristic graph (TCG) of imines as an efficient Molecule ID Card was introduced. The TCG can be used to quantitatively diagnose and predict the characteristic chemical properties of imines and their various reaction intermediates as well as the reduction mechanism of the imines. The information disclosed in this work could not only supply a gap of thermodynamics for the chemistry of imines but also strongly promote the fast development of the applications of imines. 2009 American Chemical Society.

Mild conditions for Pd-catalyzed conversion of aryl bromides to primary anilines using benzophenone imine

Mild (30 °C) and efficient (53-91%) conversion of aryl bromides to primary anilines using a Pd-catalyzed amination strategy is described. A detailed account of the ligand optimization, base and solvent selection, and general substrate scope of this methodology is described herein.

Arylamine synthesis

The present invention provides a method for the preparation of a wide range of primary arylamines. The arylamines are prepared in two efficient, straightforward transformations: 1) an activated aryl group and an imine group are combined, in the presence o