Iridium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen-Bonding and sp3-C-H Noncovalent Interactions was written by Murayama, Hiroaki;Heike, Yoshito;Higashida, Kosuke;Shimizu, Yohei;Yodsin, Nuttapon;Wongnongwa, Yutthana;Jungsuttiwong, Siriporn;Mori, Seiji;Sawamura, Masaya. And the article was included in Advanced Synthesis & Catalysis in 2020.Quality Control of Phenyl(pyridin-2-yl)methanone This article mentions the following:
Iridium-catalyzed enantioselective transfer hydrogenation of ketones with formic acid was developed using a prolinol-phosphine chiral ligand. Cooperative action of the iridium atom and the ligand through alc.-alkoxide interconversion was crucial to facilitate the transfer hydrogenation. Various ketones including alkyl aryl ketones, ketoesters, and an aryl heteroaryl ketone were competent substrates. An attractive feature of this catalysis was efficient discrimination between the alkyl and aryl substituents of the ketones, promoting hydrogenation with the identical sense of enantioselection regardless of steric demand of the alkyl substituent and thus resulting in a rare case of highly enantioselective transfer hydrogenation of tert-alkyl aryl ketones. Quantum chem. calculations revealed that the sp3-C-H/锜?interaction between an sp3-C-H bond of the prolinol-phosphine ligand and the aryl substituent of the ketone was crucial for the enantioselection in combination with O-H璺矾璺疧/sp3-C-H璺矾璺疧 two-point hydrogen-bonding between the chiral ligand and carbonyl group. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Quality Control of Phenyl(pyridin-2-yl)methanone).
Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of 閳?8.7 鑴?10閳? cm3璺痬ol閳?.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ璺痬ol閳? in the liquid phase and 140.4 kJ璺痬ol閳? in the gas phase. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Quality Control of Phenyl(pyridin-2-yl)methanone