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Metal-free activation of H2O2 by synergic effect of ionic liquid and microwave: chemoselective oxidation of benzylic alcohols to carbonyls and unexpected formation of anthraquinone in aqueous condition

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Abstract

H2O2 mediated oxidation of alcohols in ionic liquid is revisited, wherein, ionic liquids under the influence of microwave irradiation have been found to facilitate activation of H2O2 without any metal catalyst in aqueous condition. The method utilizes a neutral ionic liquid [hmim]Br both as catalyst and solvent for efficient and chemoselective oxidation of benzyl alcohol derivatives on aromatic (β, γ) alcohols, cyclic and aliphatic analogues, which can be a useful synthetic approach in total synthesis of complex organic compounds/natural products. Moreover, an unexpected oxidation of 9-anthracenyl propanol, a polyaromatic benzyl alcohol, resulting in the formation of 9,10-anthraquinone by the loss of propyl side chain was observed. Plausible mechanism and further exploration of this method on various other related substrates are discussed in detail.

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Authors and Affiliations

  1. Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Council of Scientific and Industrial Research, Palampur, HP, 176061, India

    Rakesh Kumar, Nandini Sharma, Naina Sharma, Abhishek Sharma & Arun K. Sinha

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  1. Rakesh Kumar
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  2. Nandini Sharma
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  3. Naina Sharma
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  4. Abhishek Sharma
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  5. Arun K. Sinha
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Correspondence to Arun K. Sinha.

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Kumar, R., Sharma, N., Sharma, N. et al. Metal-free activation of H2O2 by synergic effect of ionic liquid and microwave: chemoselective oxidation of benzylic alcohols to carbonyls and unexpected formation of anthraquinone in aqueous condition. Mol Divers 15, 687–695 (2011). https://doi.org/10.1007/s11030-010-9292-z

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