A practical synthesis of tris(pyrazolyl)methylaryls.

The preparation of three tris(pyrazolyl)toluidines from trifluoromethylaniline reagents is described that likely takes advantage of (quinoidal) resonance-stabilized activation of the C-F bonds. Subsequent transformations lead to two additional (for a total of five new) tris(pyrazolyl)methylaryls. This simple reaction is remarkable because only one other tris(pyrazolyl)methylaryl has been reported previously, because it is usually very difficult to activate fluoroalkane C-F bonds, and because of the potential scope of the reaction.