Aerobic oxidation with N-hydroxyphthalimide catalysts in ionic liquid

Wang, J.; Liu, Lei; Wang, Yefeng; Zhang, Ying; Deng, Wei; Guo, Qi

doi:10.1016/j.tetlet.2005.04.136

Cited by 66 publications

(28 citation statements)

References 22 publications

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“…Again, we interpret these results in term of increased solubility of Co(II) ions in the presence of IL. Interestingly, the addition of NHPI to the Co(II)/IL systems caused a further increase in the conversion of EB (Table 4, entries [13][14][15][16][17][18][19][20]. The biggest effect was observed in the CoCl 2 and Co(OAc) 2 cases.…”

Section: Entrymentioning

confidence: 97%

Solvent‐Free Aerobic Oxidation of Ethylbenzene Promoted by NHPI/Co(II) Catalytic System: The Key Role of Ionic Liquids

et al. 2019

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The synergistic action between imidazolium based ionic liquid (IL) [bmim][OcOSO3] and Co(II)/N‐hydroxyphthalimide (NHPI) systems in the catalytic aerobic oxidation of ethylbenzene under solvent‐free conditions have been here demonstrated by reaching a 35 % conversion with 83 % of selectivity in acetophenone at 80 °C. This highly performing catalytic system have been selected after screening several different IL and Co(II) salt combinations, and making sure that the complete solubilization of the polar NHPI in the lipophilic medium, without thus requiring any chemical modification of the organic catalyst, could be attained. This solubilizing effect can be ascribed to a direct interaction between [bmim][OcOSO3] IL and NHPI as revealed by a detailed NMR investigation which also allowed to exclude the formation of higher IL aggregates in the form of micelles or vesicles.

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Section: Entrymentioning

confidence: 97%

Solvent‐Free Aerobic Oxidation of Ethylbenzene Promoted by NHPI/Co(II) Catalytic System: The Key Role of Ionic Liquids

et al. 2019

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“…The 3‐pyridinylmethyl‐ N ‐hydroxyphthalimide‐catalyzed aerobic oxidation of N ‐alkylamides to imides occurs better in ionic liquids than in conventional organic solvents 117. The combination of MnO 2 /NHPI system describes a highly efficient catalytic oxidation of nitrotoluenes to nitrobenzoic acids with air 118…”

Section: Oxidation Of Activated Sp3 Ch Bonds With O2mentioning

confidence: 99%

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

et al. 2012

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Although catalytic reductions, cross‐couplings, metathesis, and oxidation of CC double bonds are well established, the corresponding catalytic hydroxylations of CH bonds in alkanes, arenes, or benzylic (allylic) positions, particularly with O2, the cheapest, “greenest”, and most abundant oxidant, are severely lacking. Certainly, some promising examples in homogenous and heterogenous catalysis exist, as well as enzymes that can perform catalytic aerobic oxidations on various substrates, but these have never achieved an industrial‐scale, owing to a low space‐time‐yield and poor stability. This review illustrates recent advances in aerobic oxidation catalysis by discussing selected examples, and aims to stimulate further exciting work in this area. Theoretical work on catalyst precursors, resting states, and elementary steps, as well as model reactions complemented by spectroscopic studies provide detailed insight into the molecular mechanisms of oxidation catalyses and pave the way for preparative applications. However, O2 also poses a safety hazard, especially when used for large scale reactions, therefore sophisticated methodologies have been developed to minimize these risks and to allow convenient transfer onto industrial scale.

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“…310 • C and 550 • C were observed owing to little amount of manganese oxides compared with pure manganese acetate. However, it was also possible that a part of low valency Mn 2+ was oxidized to high valencies of Mn 3+ or Mn 4+ for Mn supported HMS silicas calcined at 550 • C according to decomposition of pure manganese acetate at 310-650 • C. Table 3 lists the catalytic activity data, together with selectivity for 4-t-butylbenzaldehyde (ArCHO), 4-t-butylbenzyl alcohol (ArCH 2 OH) and 4-t-butyl-benzyl acid (ArCOOH) in oxidation reaction of 4-t-butyltoluene (ArCH 3 ) with O 2 over the catalysts using NHPI, a commercially available compound prepared easily as free radical promoter [8,48]. The actions of NHPI and the catalysts were initially tested.…”

Section: Mn(ch 3 Coo)mentioning

confidence: 99%