22627-00-5

Upstream product

• 71103-88-3 [1-Phenyl-1-o-tolyl-meth-(E)-ylideneaminooxy]-ethaneperoxoic acid tert-butyl ester 
• 932-31-0 ortho-tolylmagnesium bromide 
• 100-47-0 benzonitrile 
• 529-19-1 2-Methylbenzonitrile 
• 108-86-1 bromobenzene 
• 591-51-5 phenyllithium 
• 118-90-1 ortho-methylbenzoic acid 
• 85515-91-9 (2-methylphenyl)phenylmethanone oxime 
• 71104-28-4 o-Methyldiphenylmethylenamino-oxyacetylchlorid 
• 56483-73-9 o-Methyldiphenylmethylenaminooxyessigsaeure 
• 95-46-5 2-methylphenyl bromide 
• 2936-57-4 <(2-Methylphenyl)phenylmethylene>ammonium chloride 

Downstream Products

• 119208-73-0 α-Methoxy-N-(phenyl-o-tolylmethylen)benzylamin 
• 86-73-7 9H-fluorene 
• 529-19-1 2-Methylbenzonitrile 
• 120-12-7 anthracene 
• 56153-61-8 2-benzyl-benzonitrile 
• 100-47-0 benzonitrile 
• 110900-28-2 WOF₄NC(C₆H₅)(C₆H₄CH₃)^(1-) 
• 131-58-8 2-Methylbenzophenone 
• 2936-62-1 (RS)-(2-methylphenyl)phenylmethylamine 
• 213128-16-6 N-[1-Phenyl-1-o-tolyl-meth-(E)-ylidene]-benzamide 

Relevant academic research and scientific papers

Light-Driven Enantioselective Synthesis of Pyrroline Derivatives by a Radical/Polar Cascade Reaction

Herein, a light-driven, atom-economical process that provides access to enantiomerically enriched substituted chiral 1-pyrroline derivatives is introduced. The strategy involves the distal functionalization of acyl heterocycles through a hydrogen-atom transfer (HAT) process and the use of tailor-made ketimines as reliable electrophilic partners. This transformation is translated into an enantiomerically controlled radical/polar cascade reaction in which water is produced as the sole by-product and stereoselectivity is dictated by coordination to a chiral-at-rhodium catalyst.

Copper-catalyzed [2+3]-annulation of N-H imines with vinyl azides: Access to polyaryl 2: H -imidazoles

A practical method for the synthesis of 2H-imidazoles via a [2+3] annulation of N-H imines with vinyl azides using a copper catalyst is developed. In this conversion, environmentally friendly oxygen is used as the sole oxidant and N2 and H2O are the only by-products. The catalytic transformation, operating under mild conditions, is operationally simple and is considered as a readily available catalytic system having good substrate and functional compatibility with high atom-efficiency without the need for additional ligands or additives.

Hydrogen bond directed aerobic oxidation of amines via photoredox catalysis

An application of H-bonding interactions for directing the α-C-H oxidation of amines to amides and amino-ketones catalyzed by an organic photocatalyst is reported. The high efficiency of this method is demonstrated by the aerobic oxidation of pyrrolidines, diarylamines and benzylamines bearing urea groups with high yields and a wide substrate scope.

Introducing Glycerol as a Sustainable Solvent to Organolithium Chemistry: Ultrafast Chemoselective Addition of Aryllithium Reagents to Nitriles under Air and at Ambient Temperature

Edging closer towards developing air and moisture compatible polar organometallic chemistry, the chemoselective and ultrafast addition of a range of aryllithium reagents to nitriles has been accomplished by using glycerol as a solvent, at ambient temperature in the presence of air, establishing a novel sustainable access to aromatic ketones. Addition reactions occur heterogeneously (“on glycerol conditions”), where the lack of solubility of the nitriles in glycerol and the ability of the latter to form strong intermolecular hydrogen bonds seem key to favouring nucleophilic addition over competitive hydrolysis. Remarkably, PhLi exhibits a greater resistance to hydrolysis working “on glycerol” conditions than “on water”. Introducing glycerol as a new solvent in organolithium chemistry unlocks a myriad of opportunities for developing more sustainable, air and moisture tolerant main-group-metal-mediated organic synthesis.

Synthesis of iron hydrides by selective C-F/C-H bond activation in fluoroarylimines and their applications in catalytic reduction reactions

The reactions of Fe(PMe3)4 with different 2,6-diflurophenylarylimines 1-5 were explored. Fluoroarylimines 1-3, the aryl rings of which are substituted with electron-withdrawing groups, reacted with Fe(PMe3)4 to afford the C-H activation products 6-8. However, if the aryl rings of the fluoroarylimines were substituted with electron-donating groups, the iron hydrides 9 and 10 were obtained from the reactions of the fluoroarylimines with Fe(PMe3)4 through C-F bond activation. In a further study, silanes, especially triethoxysilane, were found to benefit the reactions and improve the yields of the hydridoiron complexes. The three-component reaction of Fe(PMe3)4, a fluoroarylimine, and a silane could also be utilized in reactions involving 2,6-(CH3)2C6H3-C(=NH)-2,6-F2C6H3 (13) and 2,6-F2C6H3-C(=NH)-C6F5 (16) to synthesize iron hydrides (15 and 18). The hydridoiron complexes could be utilized as efficient catalysts in the hydrosilylation of aldehydes and ketones. Furthermore, cinnamaldehydes were selectively reduced to the corresponding cinnamyl alcohols in high yields. The mechanism of the catalytic reduction reaction was studied extensively through operando IR spectroscopy.

Synthesis of aryl ketones via decarboxylation of aromatic acids under solvothermal condition

Aryl ketones were prepared by the condensation of aromatic carboxylic acids with alkyl/aryl nitrile via the decarboxylation of carboxylic acids under solvothermal condition. All the compounds were characterized by comparing with standard samples prepared by the known literature method.

Synthesis and characterization of new ca-disubstituted (diarylaminomethyl)phosphonates

A convenient and efficient three-step procedure for the preparation of W-protected or unprotected C-disubstituted (di-arylaminomethyOphosphonates 1 is reported. This method allows diversification of the substituents on the carbon in the a-position to the phosphorus, as well as the protective group on the amine and the phosphonate ester group.

2-Azaallenium Salts from N-Benzylidene-α-methoxybenzylamines

New phenyl-substituted 2-azaallenium salts 1 with variable substitution pattern were synthesized in high yields and under mild reaction conditions by treatment of N-benzylidene-α-methoxy-benzylamines 4 with acylium salts.The amines 4 are easily accessible from imines 2 and α-chloro ethers 3 or from 2,4-diaza-1,4-pentadiones 7; only in the case of strong steric hindrance an alternate reaction (forming imidazole 6) takes place.Some of the new 2-azaallenium salts (1ea-1ed, 1fa-1fd) show high tendency for intramolecular cyclisation reactions leading to isoquinoline derivatives 8 and 9. - The structures of the salts 1 in solution were analysed on the basis of 1H- and 13C-NMR spectra with respect to the dynamic behaviour of the cations.For 1aa-1j cumulene structures were derived, for the intensively coloured 1k, however, a 2-azaallyl cation structure of the aza-trimethine dyestuff type was found (IR data). - Keywords: 2-Azaallenium Salts; N-Benzylidene-α-methoxybenzylamines

Empirical Substituent Parameters for E/Z Equilibrium Constants

A set of substituent parameters λd is proposed which permits the prediction of E/Z equilibrium constants for olefins, enamines, Schiff bases, hydrazones, semicarbazones, oximes, and nitrones.The set includes values for the "non-bonded" electron pairs and the nitrone oxygen as well as for amino or phenyl groups coplanar and orthogonal to the double bond.Ketone anils prefer a perpendicular phenyl group.Principal limitations of the very simple heuristic model are discussed.The model is also applied to the "cis"- and "ortho"-effects, enolates, and Schiff bases of cyclic and bicyclic ketones.