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

Author:
Iaroshenko, Viktor O., Gevorgyan, Ashot, Mkrtchyan, Satenik, Arakelyan, Knar, Grigoryan, Tatevik, Yedoyan, Julietta, Villinger, Alexander, Langer, Peter
Source:
Journal of organic chemistry 2015 v.80 no.4 pp. 2103-2119
ISSN:
1520-6904
Subject:
Suzuki reaction, arylation, chemical structure, halides, nitroimidazoles, organic chemistry, reaction mechanisms, regioselectivity
Abstract:
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.
Agid:
5505119