Hydrogen Peroxide or Peracetic Acid Mediated Self-Titrating α-Halogenation of 1,3-Dicarbonyl Compounds

Ramulu Akula, Marc J. Galligan, Hasim Ibrahim*

*Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland, Email: hasim.ibrahimucd.ie

R. Akula, M. J. Galligan, H. Ibrahim, Synthesis, 2011, 347-351.

DOI: 10.1055/s-0030-1258367

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Abstract

Efficient oxidative α-halogenation of 1,3-dicarbonyl compounds has been achieved by employing a system comprising of sub-stoichiometric amounts of TiX₄ (X = Cl, Br) in the presence of environmentally benign hydrogen peroxide (H₂O₂) or peracetic acid (MeCO₃H) as the oxidants. The end point of the reaction is accompanied by a sharp colour change.

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Unified Strategy for Iodine(III)-Mediated Halogenation and Azidation of 1,3-Dicarbonyl Compounds

M. J. Galligan, R. Akula, H. Ibrahim, Org. Lett., 2014, 16, 600-603.

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Key Words

halogenation, α-chlorination, α-bromination, peracetic acid, titanium, halides, electrophilic

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ID: J66-Y2011-0190