Selective α-Deuteration of Cinnamonitriles using D2O as Deuterium Source was written by Guo, Beibei;de Vries, Johannes G.;Otten, Edwin. And the article was included in Advanced Synthesis & Catalysis in 2022.Formula: C12H9NO This article mentions the following:
The selective α-deuteration of α,β-unsaturated nitriles using the strong base t-BuOK or a metal-ligand cooperative Ru pincer catalyst was described. With D2O as deuterium source and glyme as solvent at 70°C, t-BuOK is an efficient catalyst for deuteration at the α-C(sp2) position of cinnamonitriles, providing access to a broad range of deuterated derivatives in good to excellent yields and with very high levels of deuterium incorporation. While the t-BuOK-catalyzed protocol does not tolerate base-sensitive functional groups, cinnamonitrile derivatives containing a benzylic bromide or ester moiety were deuterated in excellent yields using Milstein’s ruthenium PNN pincer catalyst. Moreover, the activity for H/D exchange of the metal-ligand cooperative Ru catalyst was found to be significantly higher than that of t-BuOK, allowing reactions to proceed well even at room temperature A mechanistic proposal is put forward that involves deprotonation of the cinnamonitrile α-CH position when using t-BuOK as catalyst, whereas H/D exchange catalysis with the Ru PNN pincer likely proceeds via (reversible) oxa-Michael addition of D2O. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Formula: C12H9NO).
Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Formula: C12H9NO