Journal of Organic Chemistry 2007-12-07

A practical synthesis of tris(pyrazolyl)methylaryls.

Brendan J Liddle, James R Gardinier

Index: J. Org. Chem. 72 , 9794, (2007)

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Abstract

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.