Organocatalyzed α-Deuteration of Ketones and Bioactive Carbonyl Compounds Using D2O as Deuterium Source

Abstract

In this report, we disclose an organocatalyzed deuteration process of α-C-H bonds in ketones using D₂O as economical deuterium source under mild reaction conditions. This protocol enables good to excellent deuterium incorporation (90%–97%) in diverse ketones in a single run. The value of this methodology is further demonstrated by deuteration of commercially available bioactive ketones such as 2-acetylphenothiazine, nabumetone, pentoxifylline, and estrone-3-methyl ether. Furthermore, the practicality of the developed protocol is justified by scale-up studies.