Oxidative Kinetic Resolution of Aromatic Alcohols Using Iron Nanoparticles was written by Sonnenberg, Jessica F.;Pichugin, Dmitry;Coombs, Neil;Morris, Robert H.. And the article was included in Topics in Catalysis in 2013.HPLC of Formula: 120121-01-9 This article mentions the following:
Using the transfer hydrogenation (TH) pre-catalyst trans-(R,R)[Fe(NCMe)CO(PPh2C6H4CH = NCHPh-)2][BF4]2 (1) the authors studied the reverse reaction, oxidative kinetic resolution, and were able to achieve turn-over frequencies up to 335 h-1 and s-values in favor of the (R)-alc. up to 10.2. Using racemic 1-phenylethanol the authors optimized reaction conditions to maximize enantioselectivity and turn-over frequency (TOF) and studied the effect of different proton/hydride acceptors, temperatures, and bases. Using KOCMe3 as the base and benzophenone in THF as the solvent and acceptor at 45°, the authors tested substrates with varying electronic and steric factors. By increasing the steric bulk at the alc., the enantioselectivity increased, however the TOF decreased dramatically. Varying the electronics of the substrates using electron withdrawing and donating substituents showed a less significant effect. Probably the active species in catalysis is zero-valent iron nanoparticles (Fe NPs), a postulate that the authors support with microscopy imaging, sub-stoichiometric poisoning experiments, and anal. of the reaction profile. Further support is given in terms of a polymer-supported substrate experiment whereby the active species in catalysis is too large to permeate the pores of a functionalized polymer. Probably this is the 1st reported example of using a nanoparticle surface for oxidative kinetic resolution In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9HPLC of Formula: 120121-01-9).
(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.HPLC of Formula: 120121-01-9
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts