Direct Synthesis of Amides from Benzonitriles and Benzylic Alcohols via a KOt-Bu-Mediated MPV-type Hydrogen Transfer Process was written by Li, Gaolin;Li, Meichen;Xia, Zhen;Tan, Ze;Deng, Wei;Fang, Chen. And the article was included in Journal of Organic Chemistry in 2022.Application of 105-13-5 This article mentions the following:
Meerwein-Ponndorf-Verley (MPV)-type reduction between benzonitriles and benzylic alcs. under transition-metal-free conditions has been demonstrated for the first time. Using simple KOt-Bu as the base, various benzonitriles can be efficiently reduced by benzylic alcs. via hydrogen transfer reduction, and the resultant Ph imine can react further with benzylic alcs. to give amides as the final product in which both the alcs. and the nitriles are incorporated. Preliminary mechanistic investigations indicated that the reaction may go through multiple MPV-type hydrogen transfer processes. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Application of 105-13-5).
(4-Methoxyphenyl)methanol (cas: 105-13-5) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Application of 105-13-5
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem