31197-65-6

Upstream product

• 5431-31-2 α-hydroxyphenylacetic acid hexyl ester 
• 93-56-1 phenylethane 1,2-diol 
• 111-27-3 hexan-1-ol 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 611-73-4 Benzoylformic acid 

Relevant academic research and scientific papers

ZnO nanoparticles: An efficient catalyst for transesterification reaction of α-keto carboxylic esters

Pure ZnO nanoparticles were synthesized by a sustainable precipitation method using zinc nitrate and sodium hydroxide in aqueous medium at room temperature. They were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM-EDX), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FTIR), ultraviolet-visible spectroscopy (UV–vis) spectroscopy and Brunauer-Emmett-Teller (BET) analysis. The XRD patterns indicate the formation of the hexagonal wurtzite phase with high purity and SEM-EDS analysis confirm the purity and a homogenous distribution of the nanostructures. The ZnO nanostructures present plate-like agglomerates, resulting in a quasi-spherical morphology. The catalytic activity of the formed ZnO nanoparticles was evaluated towards the transesterification reaction of different carboxylic esters in the presence of various alcohols. This catalyst is highly selective for the transesterification of α-keto carboxylic ester (methyl benzoylformate) and leads to ca. 97percent of product yield within 24 h of reaction time.

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.

CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides

Although aerobic oxidative acylation of amides with alcohols would be a good complement to classical synthetic methods for imides (e.g., acylation of amides with activated forms of carboxylic acids), to date, there have been no reports on oxidative acylation to produce imides. In this study, we successfully developed, for the first time, an efficient method for the synthesis of imides through aerobic oxidative acylation of amides with alcohols by employing a CuCl/TMEDA/nor-AZADO catalyst system (TMEDA = teramethylethylendiamine; nor-AZADO = 9-azanoradamantane N-oxyl). The proposed acylation proceeds through the following sequential reactions: aerobic oxidation of alcohols to aldehydes, nucleophilic addition of amides to the aldehydes to form hemiamidal intermediates, and aerobic oxidation of the hemiamidal intermediates to give the corresponding imides. This catalytic system utilizes O2 as the terminal oxidant and produces water as the sole by-product. An important point for realizing this efficient acylation system is the utilization of a TMEDA ligand, which, to the best of our knowledge, has not been employed in previously reported Cu/ligand/N-oxyl systems. Based on experimental evidence, we consider that plausible roles of TMEDA involve the promotion of both hemiamidal oxidation and regeneration of an active CuII-OH species from a CuI species. Here promotion of hemiamidal oxidation is particularly important. Employing the proposed system, various types of structurally diverse imides could be synthesized from various combinations of alcohols and amides, and gram-scale acylation was also successful. In addition, the proposed system was further applicable to the synthesis of α-ketocarbonyl compounds (i.e., α-ketoimides, α-ketoamides, and α-ketoesters) from 1,2-diols and nucleophiles (i.e., amides, amines, and alcohols).

Chiral-at-metal octahedral iridium catalyst for the asymmetric construction of an all-carbon quaternary stereocenter

Metal-templated organocatalysis: The enantioselective formation of an all-carbon quaternary stereocenter is catalyzed by the ligand sphere of an inert bis-cyclometalated iridium complex (see picture). In this complex, the metal-centered chirality serves as the sole source for the effective asymmetric induction. Copyright

Chiral cobalt-catalyzed enantioselective aerobic oxidation of α-hydroxy esters

A chiral cobalt-catalyzed enantioselective aerobic oxidative kinetic resolution of (±)-α-hydroxy esters, using molecular oxygen as a sole oxidant, is reported and a maximum of selectivity factor (s) 31.9 was achieved with >99% enantiomeric excess for unreacted α-hydroxy esters.