Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes was written by Liu, Yonghai;Yu, Yang;Sun, Chengyu;Fu, Yiwei;Mang, Zhiguo;Shi, Lei;Li, Hao. And the article was included in Organic Letters in 2020.Electric Literature of C12H9NO This article mentions the following:
We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcs. avoiding overoxidn. to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcs. (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Electric Literature of 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. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Electric Literature of C12H9NO