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.
Liddle
Brendan J
BJ
Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881, USA.
Gardinier
James R
JR
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry
D011720:Pyrazoles