Transition-Metal-Catalyzed Arylation of Nitroimidazoles and Further Transformations of Manipulable Nitro Group

Pd- or Ni-catalyzed C–H arylation
of 4-nitroimidazole derivatives
directed by a manipulable nitro group was developed. The reaction
tolerates a wide range of substituted aryl halides and 4-nitroimidazoles.
The experiments indicated that the nitro group has influence on regioselectivity
of the reaction. In addition, we have shown that the efficiency of
the Suzuki–Miyaura cross-coupling reaction of nitroimidazoles
is slightly lower in comparison to the direct C–H arylation.
The exploration of the chemical potential of the nitro group and a
putative reaction mechanism are discussed.