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A practical synthesis of tris(pyrazolyl)methylaryls.

The Journal of organic chemistry (2007-11-13)
Brendan J Liddle, James R Gardinier
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Potassium tri(3,5-dimethyl-1-pyrazolyl)borohydride, 97%