Oxidation of alkanes and secondary alcohols to ketones with <i>tert</i>‐butyl hydroperoxide catalyzed by a water‐soluble ruthenium complex under solvent‐free conditions

Zhang, Yuecheng; Zhao, Liyuan; Zhang, Hongyu; Huang, Rong; Zhao, Jiquan

doi:10.1002/aoc.3709

Applied Organom Chemis

2017

DOI: 10.1002/aoc.3709

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Oxidation of alkanes and secondary alcohols to ketones with tert‐butyl hydroperoxide catalyzed by a water‐soluble ruthenium complex under solvent‐free conditions

Yuecheng Zhang

Liyuan Zhao

Hongyu Zhang

et al.

Abstract: An easily synthesized water-soluble ruthenium complex, [C 6 H 5 CH 2 N(CH 3 ) 2 H] 2 [Ru(dipic)Cl 3 ] (dipic =2,6-pyridinedicarboxylate), as a catalyst showed high efficiency in the oxidation of alkanes and secondary alcohols to their corresponding ketones under solvent-free and low-catalyst-loading conditions. This catalytic system could tolerate a variety of substrates and gave the corresponding ketones in good to excellent yields. The products were easily separated and purified due to the water solubility o… Show more

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Cited by 11 publications

References 51 publications

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Catalytic activity of nickel(II), copper(II) and oxovanadium(II)‐dihydroindolone complexes towards homogeneous oxidation reactions

Adam

2018

Applied Organom Chemis

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Three novel paramagnetic metal complexes (MH 2 ID) of Ni 2+ , Cu 2+ and VO 2+ ions with 3-hydroxy-3,3'-biindoline-2,2'-dione (dihydroindolone, H 4 ID) were synthesized and characterized by different spectroscopic methods. The ligand (H 4 ID) was synthesized via homocoupling reaction of isatin in presence of phenylalanine in methanol. Complexation of low valent Ni 2+ , Cu 2+ ions and high valent VO 2+ ions with H 4 ID carried out in 1: 2 molar ratios. A comparison in the catalytic potential of paramagnetic complexes of low and high valent metal ion was explored in the oxidation processes of cis-cyclooctene, benzyl alcohol and thiophene by an aqueous H 2 O 2 , as a green terminal oxidant, in the presence and absence of acetonitrile, as an organic solvent, at 85°C. NiH 2 ID, CuH 2 ID and VOH 2 ID show good catalytic activity, i.e. good chemoand regioselectivity. VOH 2 ID has the highest catalytic potential compared to both Ni 2+and Cu 2+ -species in the same homogenous aerobic atmosphere.Catalytic oxidation of other alkenes and alcohols was also studied using NiH 2 ID, CuH 2 ID or VOH 2 ID as a pre-catalyst by an aqueous H 2 O 2 . A mechanistic pathway for those oxidation processes was proposed.

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Catalytic activity of nickel(II), copper(II) and oxovanadium(II)‐dihydroindolone complexes towards homogeneous oxidation reactions

Adam

2018

Applied Organom Chemis

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Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Al-Hussein

Adam

2020

Applied Organom Chemis

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N‐Salicylidene amino acid Schiff base sodium sulfonate salt, as a tridentate dibasic chelating ligand, was obtained from the common condensation of salicylaldehyde‐5‐sodium sulfonate with tyrosine (HPST). The internal formed ligand coordinated to Cu2+ ion in an aqueous media affording new Cu (II)‐complex (Cu‐PST), which characterized by various physico‐chemicals spectral tools. The mononuclear complex was evaluated as a homogeneous and heterogeneous catalyst in the (ep)oxidation protocols of 1,2‐cyclooctene and benzyl alcohol. Heterogeneously, Cu‐PST was immobilized on Fe3O4‐SiO2, as nanoparticles. The heterogeneous catalyst was characterized by infrared, X‐ray diffraction, scanning electron microscopy, transmission electron microscopy, energy‐dispersive spectroscopy, Brunauer−Emmett−Teller and magnetism. Homogeneously, the temperature, solvent and oxidant influences were examined in the catalytic reactions to realize the best reaction conditions. Cu‐catalyst exhibited better catalytic performance in the (ep)oxidation processes homogeneously than that in the heterogeneous phase at 80°C for 2 hr in acetonitrile. Reusability of the homogeneous catalyst was for a maximum of three times in the (ep)oxidation reaction, whereas the heterogeneous catalyst was active for six times. A mechanistic pathway was proposed for both catalysts, comparatively.

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Catalytic comparison of various polar Zn(II)-Schiff base complexes and VO(II)-Schiff base complexes in (ep)oxidation processes of 1,2-cyclohexene and cyclohexane

2019

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Oxidation of alkanes and secondary alcohols to ketones with tert‐butyl hydroperoxide catalyzed by a water‐soluble ruthenium complex under solvent‐free conditions

Cited by 11 publications

References 51 publications

Catalytic activity of nickel(II), copper(II) and oxovanadium(II)‐dihydroindolone complexes towards homogeneous oxidation reactions

Catalytic activity of nickel(II), copper(II) and oxovanadium(II)‐dihydroindolone complexes towards homogeneous oxidation reactions

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Catalytic comparison of various polar Zn(II)-Schiff base complexes and VO(II)-Schiff base complexes in (ep)oxidation processes of 1,2-cyclohexene and cyclohexane

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