1703-51-1Relevant articles and documents
REGIOSELECTIVE OXIDATION OF INTERNAL OLEFINS BEARING NEIGHBORING OXYGEN FUNCTIONS BY MEANS OF PALLADIUM CATALYSTS. A DIRECT PREPARATION OF γ-KETO ESTERS AND 1,4-DIKETONES FROM β,γ-UNSATURATED ESTERS AND KETONES
Nagashima, Hideo,Sakai, Kiyomi,Tsuji, Jiro
, p. 859 - 860 (1982)
γ-Keto esters and 1,4-diketones were prepared by the palladium-catalyzed regioselective oxidation of β,γ-unsaturated esters and ketones.The best yields were obtained when the reaction was carried out using PdCl2/CuCl/O2 catalyst system in aqueous dioxane.
Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
Ma, Xiaofeng,Dewez, Damien F.,Du, Le,Luo, Xiya,Markó, István E.,Lam, Kevin
, (2018/10/15)
Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
Cp* iridium precatalysts for selective C-h oxidation with sodium periodate as the terminal oxidant
Zhou, Meng,Hintermair, Ulrich,Hashiguchi, Brian G.,Parent, Alexander R.,Hashmi, Sara M.,Elimelech, Menachem,Periana, Roy A.,Brudvig, Gary W.,Crabtree, Robert H.
supporting information, p. 957 - 965 (2013/04/23)
Sodium periodate (NaIO4) is shown to be a milder and more efficient terminal oxidant for C-H oxidation with CpIr (Cp* = C 5Me5) precatalysts than ceric(IV) ammonium nitrate. Synthetically useful yields, regioselectivities, and functional group tolerance were found for methylene oxidation of substrates bearing a phenyl, ketone, ester, or sulfonate group. Oxidation of the natural products (-)-ambroxide and sclareolide proceeded selectively, and retention of configuration was seen in cis-decalin hydroxylation. At 60 C, even primary C-H bonds can be activated: whereas methane was overoxidized to CO2 in 39% yield without giving partially oxidized products, ethane was transformed into acetic acid in 25% yield based on total NaIO4. 18O labeling was demonstrated in cis-decalin hydroxylation with 18OH2 and NaIO 4. A kinetic isotope effect of 3.0 ± 0.1 was found in cyclohexane oxidation at 23 C, suggesting C-H bond cleavage as the rate-limiting step. Competition experiments between C-H and water oxidation show that C-H oxidation of sodium 4-ethylbenzene sulfonate is favored by 4 orders of magnitude. In operando time-resolved dynamic light scattering and kinetic analysis exclude the involvement of metal oxide nanoparticles and support our previously suggested homogeneous pathway.
