Mechanistic investigation of the iridium-catalysed alkylation of amines with alcohols was written by Fristrup, Peter;Tursky, Matyas;Madsen, Robert. And the article was included in Organic & Biomolecular Chemistry in 2012.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:
The [Cp*IrCl2]2-catalyzed alkylation of amines with alcs. was investigated using a combination of exptl. and theor. methods. A Hammett study involving a series of para-substituted benzyl alcs. resulted in a line with a neg. slope. This clearly documents that a pos. charge is built up in the transition state, which in combination with the measurement of a significant kinetic isotope effect determines hydride abstraction as being the selectivity-determining step under these conditions. A complementary Hammett study using para-substituted anilines was also carried out. Again, a line with a neg. slope was obtained suggesting that nucleophilic attack on the aldehyde is selectivity-determining A computational investigation of the entire catalytic cycle with full-sized ligands and substrates was performed using d. functional theory. The results suggest a catalytic cycle where the intermediate aldehyde stays coordinated to the iridium catalyst and reacts with the amine to give a hemiaminal which is also bound to the catalyst. Dehydration to the imine and reduction to the product amine also takes place without breaking the coordination to the catalyst. The fact that the entire catalytic cycle takes place with all the intermediates bound to the catalyst is important for the further development of this synthetic transformation. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).
4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Quality Control of 4-(Benzylamino)benzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts