Organorhodium-Functionalized Periodic Mesoporous Organosilica: High Hydrophobicity Promotes Asymmetric Transfer Hydrogenation in Aqueous Medium was written by Liu, Rui;Jin, Ronghua;Kong, Lingyu;Wang, Jinyu;Chen, Chen;Cheng, Tanyu;Liu, Guohua. And the article was included in Chemistry – An Asian Journal in 2013.Name: (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:
Three organosilica-bridged periodic mesoporous organosilicas were prepared by the immobilization of a chiral N-sulfonylated diamine-based organorhodium complex within their silicate network. Structural anal. and characterization confirmed their well-defined single-site active rhodium centers, while electron microscopy revealed their highly ordered hexagonal mesostructures. Among these three different organosilica-bridged periodic mesoporous organosilicas, the ethylene-bridged periodic mesoporous organosilica catalyst exhibited excellent heterogeneous catalytic activity and high enantioselectivity in the aqueous asym. transfer hydrogenation of aromatic ketones. This superior catalytic performance was attributed to its salient hydrophobicity, while its comparable enantioselectivity relative to the homogeneous catalyst was derived from the confined nature of the chiral organorhodium catalytic sites. Furthermore, this ethylene-bridged periodic mesoporous organosilica could be conveniently recovered and reused at least 12 times without the loss of its catalytic activity. This feature makes this catalyst attractive for practical organic synthesis in an environmentally friendly manner. This study offers a general way of optimizing the bridged organosilica moiety in periodic mesoporous organosilicas, thereby enhancing its catalytic activity in heterogeneous catalysis. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Name: (R)-4-(1-Hydroxyethyl)benzonitrile).
(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Name: (R)-4-(1-Hydroxyethyl)benzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts