125367-66-0

Upstream product

• 22632-90-2 4-methyl-benzophenone-imine 
• 108-86-1 bromobenzene 
• 538-51-2 benzylidene phenylamine 
• 106-38-7 para-bromotoluene 
• 63468-90-6 phenylglyoxylic acid potassium salt 
• 62-53-3 aniline 
• 611-73-4 Benzoylformic acid 
• 574-66-3 Benzophenone oxime 
• 108-88-3 toluene 
• 53060-12-1 diphenyl-p-tolylmethylamine 
• 134-84-9 4-Methylbenzophenone 

Downstream Products

• 1436743-10-0 N-(4-(hydroxy(phenyl)(p-tolyl)methyl)phenyl)acetamide 
• 1436742-96-9 N-phenyl-N-(phenyl(p-tolyl)methyl)acetamide 
• 134-84-9 4-Methylbenzophenone 

Relevant academic research and scientific papers

Metal-free tandem Beckmann-electrophilic aromatic substitution cascade affording diaryl imines, ketones, amines, and quinazolines

A cascade reaction sequence involving a Beckmann rearrangement on benzophenone oxime followed by an electrophilic aromatic substitution (EAS) on the intermediate nitrilium ion affords N-phenyl diaryl imines that may then be hydrolyzed to ketones, or reduced to the corresponding amines. Reaction with benzonitrile afforded 2,4-diphenylquinazoline through a Beckmann-Ritter-EAS cascade.

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.

Process for Preparing Azomethines from alpha-Oxocarboxylates, Amines and Aryl Bromides

A process for preparing azomethines of the general formula (V) where R is an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted alkyl radical or an optionally substituted heteroaromatic radical hav

PROCESS FOR PREPARING AZOMETHINES FROM ALPHA-OXOCARBOXYLATES, AMINES AND ARYL BROMIDES

A process for preparing azomethines of the general formula (V) where R is an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted alkyl radical or an optionally substituted heteroaromatic radical hav

Expedient synthesis of functionalized triarylmethanols through tandem formation of geminal C-C and C-O bonds

The rearrangement/oxidation of N,N-disubstituted anilines and the formal dehydrogenative cross-coupling of diarylmethanols with aniline derivatives have been developed for the preparation of symmetric and unsymmetric functionalized triarylmethanols. Both reactions proceed smoothly in trifluoroacetic acid in the presence of an inexpensive oxidant (manganese dioxide or potassium persulfate) and a catalytic amount of palladium diacetate to give a range of functionalized triarylmethanols in moderate to good yields and with extremely high regioselectivity. The two unprecedented reactions involve tandem formation of geminal C-C and C-O bonds, and they are synthetically useful, atom-efficient, and operationally simple.

Synthesis of azomethines from α-oxocarboxylates, amines and aryl bromides via one-pot three-component decarboxylative coupling

A bimetallic palladium/copper catalyst system allows the highly modular synthesis of azomethines via the decarboxylative coupling of aryl halides and α-iminocarboxylates, generated in situ from potassium α- oxocarboxylates and primary amines. The reaction proceeds already at 100a°C, a new record for redox-neutral decarboxylative cross-coupling reactions.

Development of decarboxylative coupling processes for the synthesis of azomethines and ketones

A bimetallic catalyst system has been developed that allows the synthesis of azomethines by a one-pot three-component decarboxylative coupling, starting from simple, nontoxic precursors, i.e. potassium α-oxo carboxylates, aryl halides and primary amines. In the presence of 15 mol-% copper/phenanthroline and 1 mol-% Pd/dppf, a wide range of valuable imines is conveniently accessible in high yields at 100 °C, an unprecedentedly low temperature for redox-neutral decarboxylative cross-coupling reactions. Hydrogenation of the azomethine products leads to secondary amines. Alternatively, they can be hydrolyzed in situ to aryl ketones. The resulting ketone synthesis via azomethine intermediates is also of interest as it gives higher yields at much lower temperatures than the direct decarboxylative coupling of α-oxo carboxylates with aryl halides. A convenient synthesis of azomethines by a one-pot three-component decarboxylative coupling, starting from potassium α-oxo carboxylates, aryl halides and primary amines is described. Combined with in situ hydrolysis, ketones are obtained. Thisamine-mediated ketone synthesis gives higher yields at lower temperatures than the direct coupling of α-oxo carboxylates. Copyright

Imine Insertion into a Late Metal-Carbon Bond to Form a Stable Amido Complex

An arylrhodium(I) complex containing a labile dative ligand was prepared, and its reactivity toward aryl imines was investigated. The arylrhodium(I) complex (DPPE)Rh(C5H5N)(p-tol), 2, was isolated in 65% yield from [(DPPE)Rh(μ-Cl)]2, pyridine, and p-tolyllithium. Reaction of 2 with the aldimine (p-tol)CH=N(C6H4-p-CO2Me) (3a-Tol) gave the Rh amide insertion product 4 in 88% isolated yield. The solid-state structure of 4 was determined by single-crystal X-ray diffraction. The reaction of 2 with the electron-neutral and electron-rich aldimines (Ph)CH=NPh (3b) and (p-tol)CH=N(C6H4-p-OMe) (3c) also appeared to involve insertion, but the amido complexes formed from these insertions were not stable. Thus, reaction of 2 with 3b, followed by addition of Et3NHCl, gave the amine and ketimine products (Ph)(p-tol)CH?NHPh, 5, and (p-tol)(Ph)C=N(Ph), 6, in 25% and 50% yields. Several lines of data indicate that these products are formed by a sequence of transformations involving insertion of imine to give a Rh amide intermediate, β-hydrogen elimination, cyclometalation to form a bound imine and H2, and protonolysis of the metallacycle upon addition of Et3NHCl. Consistent with this proposal, the proposed metallacycle containing the ortho-metalated ketimine ligand (p-tol)2C=N(C6H4-p-OMe) was isolated and characterized by single-crystal X-ray diffraction. Copyright