Guo, Beibei published the artcileSelective α-Deuteration of Cinnamonitriles using D2O as Deuterium Source, Quality Control of 91-02-1, the publication is Advanced Synthesis & Catalysis (2022), 364(1), 179-186, database is CAplus.
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.
Advanced Synthesis & Catalysis published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C12H9NO, Quality Control of 91-02-1.
Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem