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

Marc J. Galligan, Ramulu Akula and 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

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

DOI: 10.1021/ol403504z (free Supporting Information)


Abstract

A mild and rapid formal electrophilic α-azidation of 1,3-dicarbonyl compounds using commercially available Bu4NN3 as the azide source is mediated by (diacetoxyiodo)benzene. The reaction conditions are similar to the ones employed in analogous halogenations with Et4NX (X = Cl, Br, I).

see article for more examples



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

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


Key Words

α-chlorocarboxylic esters, α-chloroketones, α-bromocarboxylic esters, α-bromoketones, Azidation, Iodosobenzene Diacetate


ID: J54-Y2014