Highly active cooperative Lewis acid-ammonium salt catalyst for enantioselective hydroboration of ketones was written by Titze, Marvin;Heitkaemper, Juliane;Junge, Thorsten;Kaestner, Johannes;Peters, Rene. And the article was included in Angewandte Chemie, International Edition in 2021.Computed Properties of C9H9NO This article mentions the following:
Enantiopure secondary alcs. are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5-3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxo philic Lewis acid within the same catalyst mol. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Computed Properties of C9H9NO).
(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115â?25 ppm whereas in isonitriles the shifts are around 155â?65 ppm. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Computed Properties of C9H9NO
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts