7287-73-2

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 95-46-5 2-methylphenyl bromide 
• 617-00-5 2,2'-dimethyldiphenylamine 
• 95-49-8 2-methylchlorobenzene 
• 95-53-4 o-toluidine 

Relevant academic research and scientific papers

A green and mild procedure to selective synthesis of diarylamine via domino reaction of aryl halides and arginine catalyzed by magnetic-MOF

Efficient and selective direct synthesis of diarylamines from aryl halides and arginine as a nitrogen-donor reagent is reported. Arginine, which is an oral supplement, acts as a useful nitrogen source donor in the copper-catalyzed reaction. Fe3O4/Cu3(BTC)2, which was easily separated and recycled with a magnet, improved the rate and facilitation of the synthesis of diarylamines selectively. The introduction of a new and available N-source, simple magnetic separation process, normal atmospheric conditions, and excellent yields under mild reaction conditions are other important features of this work.

Palladium-catalyzed N-arylation of bis(ortho-substituted aryl)amines: An efficient method for preparing sterically congested triarylamines

Bis(ortho-substituted aryl)amines were arylated on the nitrogen atom with various haloarenes in high yields using the palladium catalyst, which was generated from palladium(II) acetate and tri(tert-butyl)phosphine. Georg Thieme Verlag Stuttgart.

Efficient copper-catalyzed coupling of aryl chlorides, bromides and iodides with aqueous ammonia

The copper(i)-catalyzed synthesis of a range of primary anilines from electron-rich and electron-deficient aryl halides including aryl chlorides has been achieved with aqueous ammonia, avoiding the need for inert atmosphere, expensive catalysts and ligands, anhydrous solvents, and additional base or other additives. The Royal Society of Chemistry 2009.

N-ALKYLATION AND N-ARYLATION OF ANILINES STARTING FROM A MILD N-Mg REAGENT: ITS ACTIVATION CAUSING THE 'N-C' COUPLING TO EXTEND THE UNIFIED STRUCTURE-REACTIVITY RELATIONSHIP

New N-alkylation and N-arylation procedures starting from anilinomagnesium (ArNHMgBr) are reported.For N-alkylation with alkyl bromides, addition of hexamethylphosphoramide to an ArNHMgBr solution in tetrahydrofuran (THF) is effective.After heating at 55 deg C, N-monoalkylation product was obtained in 60-90percent yield, slight dialkylation taking place.The combined use of aryliminodimagnesium with α,ω-dibromoalkanes led to N-arylazacycloalkanes.For N-arylation with iodobenzene, replacement of THF with pyridine and additional use of copper(I) iodide are effective.After heating at 115 deg C with iodobenzene, mono- and diarylation products were obtained, the former being predominant.The combined use of ArNHMgBr and N,N,N',N'-tetramethylethylenediamine as the ligand of copper species is effective for elimination of diarylation and other undesired products, and leads to diarylamines in excellent yield.The method is of advantage over the conventional Ullmann and Chapman methods.The polar solvents and copper salt are effective additives for inducing 'inert combinations' of ArNHMgBr or ArN(MgBr)2 with alkyl and aryl halides into N-C coupling, to extend the unified view proposed for the reactivity of magnesium reagents.The difference in the roles of N-Mg and N-Cu species is discussed.

Phase-Transfer Catalysis in the Ullmann Synthesis of Substituted Triphenylamines

A variety of substituted triphenylamine derivatives were prepared in nearly quantitative yields by the use of 18-crown-6 as a phase transfer catalyst under the Ullmann reaction conditions.