87239-90-5Relevant academic research and scientific papers
Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls
Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin
supporting information, p. 7445 - 7449 (2021/10/02)
An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.
Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species
Yusubov, Mekhman S.,Nemykin, Victor N.,Zhdankin, Viktor V.
experimental part, p. 5745 - 5752 (2010/10/02)
Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)3SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes.
Development of new recyclable reagents and catalytic systems based on hypervalent iodine compounds
Yusubov, Mekhman S.,Zhdankin, Viktor V.
scheme or table, p. 185 - 191 (2011/03/19)
Recent advances in the development of polymer-supported iodine(V) oxidants, recyclable monomeric hypervalent iodine(III) reagents and catalytic systems based on hypervalent iodine compounds are discussed. These efficient and environmentally friendly reagents and catalysts are particularly useful for oxidative transformations of alcohols to carbonyl compounds and for oxidations at the benzylic position.
Iodine(V)/ruthenium(III)-cocatalyzed oxidations: A highly efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons with oxone
Yusubov, Mekhman S.,Zagulyaeva, Aleksandra A.,Zhdankin, Viktor V.
supporting information; experimental part, p. 11091 - 11094 (2010/04/28)
An extremely mild and efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons based on Ru(III)-catalyzed reoxidation of ArIO to ArIO2 was reported, by using Oxone as a stoichiometric oxidant. Oxone was added to a mixture of propylbenzene, PhI, and RuCl3 in acetonitrile and water in five portions over 22 h under stirring at room temperature. The reaction mixture was stirred for an additional 4 h and was monitored by TLC by the disappearance of propylbenzene. Then ethyl acetate and water were added and the mixture was stirred for 5 mm. The organic solution was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with NaCl, and dried over Na2SO 4. The oxidation of the other hydrocarbons was performed by using a similar procedure. The use of smaller amounts of Oxone led to incomplete conversion owing to its noticeable decomposition with loss of oxygen gas under reaction conditions.
