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Exercise in 1-aryl-3-CF3-1H-pyrazoles: regioselective synthesis of 4-/5-iodides and cross-coupling reactions
Kamil Świątek1, Greta Utecht-Jarzyńska1, Marcin Jasiński1
1University of Lodz, Faculty of Chemistry, Department of Organic and Applied Chemistry Tamka 12 91-403 Łódź Poland mjasinski@uni.lodz.pl.
Abstract:
A series of 1-aryl-3-CF3-1H-pyrazoles was prepared and examined using iodination reactions. Treatment with n-BuLi followed by trapping of the corresponding lithium pyrazolide with elemental iodine produced 5-iodo derivatives exclusively, while CAN-mediated iodination with I2 afforded isomeric 4-iodides in a highly regioselective manner. The title iodides were demonstrated to be convenient building blocks for the preparation of more complex 3-trifluoromethylated pyrazoles through the model Suzuki-Miyaura and Sonogashira reactions.
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