Palladium(II)-Catalyzed Direct ortho-C-H Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant was written by Chan, Chun-Wo;Zhou, Zhongyuan;Yu, Wing-Yiu. And the article was included in Advanced Synthesis & Catalysis in 2011.Quality Control of N-(3-Methoxyphenyl)pivalamide This article mentions the following:
An efficient palladium-catalyzed C-H acylation with aldehydes using tert-Bu hydroperoxide (TBHP) transforms various anilides into synthetically useful 2-aminobenzophenone derivatives under mild conditions (40°, 3 h). The acylation reaction exhibits excellent regioselectivity and functional group tolerance, and simple aromatic aldehydes, functionalized aliphatic aldehydes and heteroaromatic aldehydes are effective coupling partners. The acylation reaction is probably initiated by a rate-limiting electrophilic C-H cyclopalladation (kH/kD=3.6; ρ+=-0.74) to form an arylpalladium complex, followed by acyl radical functionalization. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Quality Control of N-(3-Methoxyphenyl)pivalamide).
N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Quality Control of N-(3-Methoxyphenyl)pivalamide
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem