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.
H(2)O(2) 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 H(2)O(2) 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.
Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Council of Scientific and Industrial Research, Palampur, HP 176061, India.
Rakesh
R
Kumar
Nandini
N
Sharma
Naina
N
Sharma
Abhishek
A
Sharma
Arun K
AK
Sinha
D000880:Anthraquinones / Q000737:chemistry*; D001592:Benzyl Alcohols / Q000737:chemistry*; D002384:Catalysis; D006861:Hydrogen Peroxide / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry; D008872:Microwaves; D010084:Oxidation-Reduction
D000880:Anthraquinones; D001592:Benzyl Alcohols; D052578:Ionic Liquids; C042834:9,10-anthraquinone; D006861:Hydrogen Peroxide