Journal
MOLECULAR DIVERSITY
Volume 15, Issue 3, Pages 687-695Publisher
SPRINGER
DOI: 10.1007/s11030-010-9292-z
Keywords
Oxidation; Ionic liquids; Microwave; Metal-free; Hydrogen peroxide
Categories
Funding
- I.H.B.T., Palampur [MLP-0025]
- C.S.I.R., New Delhi
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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 (beta, gamma) 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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