Palladium-Catalyzed Amination of Aryl Nonaflates was written by Anderson, Kevin W.;Mendez-Perez, Maria;Priego, Julian;Buchwald, Stephen L.. And the article was included in Journal of Organic Chemistry in 2003.Computed Properties of C14H12N2O The following contents are mentioned in the article:
The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands such as BINAP allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions. This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Computed Properties of C14H12N2O).
4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Computed Properties of C14H12N2O
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts