51004-00-3

Upstream product

• 1013-88-3 Benzophenone imine 
• 623-00-7 4-bromobenzenecarbonitrile 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 114583-47-0 benzophenone N,N,N-trimethylhydrazonium iodide 
• 126747-14-6 4-cyanophenylboronic acid 
• 101-81-5 Diphenylmethane 
• 873-74-5 4-Aminobenzonitrile 
• 150009-08-8 1-(4-cyanophenyl)-2,2-dimethyl-1-propanone 
• 17847-33-5 phenyl 4-cyanobenzoate 
• 119-61-9 benzophenone 

Downstream Products

• 873-74-5 4-Aminobenzonitrile 
• 452070-80-3 6-(4-aminophenyl)phenanthridine 
• 274258-85-4 4-(benzhydrylamino)benzonitrile 

Relevant academic research and scientific papers

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.

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.).

Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines

N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation of N-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described.

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 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.

Nickel-Catalyzed Synthesis of Primary Aryl and Heteroaryl Amines via C-O Bond Cleavage

A nickel-catalyzed protocol for the conversion of aryl and heteroaryl alcohol derivatives to primary and secondary aromatic amines via C(sp2)-O bond cleavage is described. The new amination protocol can be applied to a range of substrates bearing diverse functional groups and uses readily available benzophenone imines as an effective nitrogen source.

A facile access for the C-N bond formation by transition metal-free oxidative coupling of benzylic C-H bonds and amides

Using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as the oxidant, we communicate an efficient oxidative C-N coupling of benzylic C-H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are well tolerated. Moreover, this reaction involves both the challenging C-H functionalization and C-N bond formation.

Cu(OAc)2-mediated cross-coupling reaction of benzophenone N,N,N-trimethylhydrazonium salts and aryl boronic acids

Cu(OAc)2-mediated coupling of benzophenone N,N,N- trimethylhydrazonium salts and aryl boronic acids proceeded to afford N-aryl imines.

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.