4534-76-3Relevant articles and documents
Ductile Pd-Catalysed Hydrodearomatization of Phenol-Containing Bio-Oils Into Either Ketones or Alcohols using PMHS and H2O as Hydrogen Source
Di Francesco, Davide,Subbotina, Elena,Rautiainen, Sari,Samec, Joseph S. M.
supporting information, p. 3924 - 3929 (2018/09/14)
A series of phenolic bio-oil components were selectively hydrodearomatized by palladium on carbon into the corresponding ketones or alcohols in excellent yields using polymethylhydrosiloxane and water as reducing agent. The selectivity of the reaction was governed by the water concentration where selectivity to alcohol was favoured at higher water concentrations. As phenolic bio-oil examples cardanol and beech wood tar creosote were studied as substrate to the developed reaction conditions. Cardanol was hydrodearomatized into 3-pentadecylcyclohexanone in excellent yield. From beech wood tar creosote, a mixture of cyclohexanols was produced. No hydrodeoxygenation occurred, suggesting the applicability of the reported method for the production of ketone-alcohol oil from biomass. (Figure presented.).
Selective activation of secondary C-H bonds by an iron catalyst: Insights into possibilities created by the use of a carboxyl-containing bipyridine ligand
Cheng, Shi,Li, Jing,Yu, Xiaoxiao,Chen, Chuncheng,Ji, Hongwei,Ma, Wanhong,Zhao, Jincai
, p. 3267 - 3273 (2013/10/01)
In this work, we report the discovery of a carboxyl-containing iron catalyst 1 (FeII-DCBPY, DCBPY = 2,2′-bipyridine-4,4′- dicarboxylic acid), which could activate the C-H bonds of cycloalkanes with high secondary (2°) C-H bond selectivity. A turnover number (TN) of 11.8 and a 30% yield (based on the H2O2 oxidant) were achieved during the catalytic oxidation of cyclohexane by 1 under irradiation with visible light. For the transformation of cycloalkanes and bicyclic decalins with both 2° and tertiary (3°) C-H bonds, 1 always preferred to oxidise the 2° C-H bonds to the corresponding ketone and alcohol products; the 2°/3° ratio ranged between 78/22 and >99/1 across 7 examples. 18O isotope labelling experiments, ESR experiments, a PPh3 method and the catalase method were used to characterize the reaction process during the oxidation. The success of 1 showed that, in addition to using a bulky catalyst, high 2° C-H bond selectivity could also be achieved using a less bulky molecular iron complex as the catalyst.
Regioselective radical ring-opening reaction of bicyclo[4.2.0]octan-2-ones promoted by samarium(II) iodide
Kakiuchi, Kiyomi,Minato, Koichi,Tsutsumi, Ken,Morimoto, Tsumoru,Kurosawa, Hideo
, p. 1963 - 1966 (2007/10/03)
Radical ring-opening reactions of bicyclo[4.2.0]octanones, its C6 alkyl derivatives, and tricyclic ketones promoted by SmI2 gave cyclohexanones via fission of the external cyclobutane bond. The CO2Me, CN, and phenyl derivatives led t