Ruthenium-Catalyzed C–H Silylation of 1-Arylpyrazole Derivatives and Fluoride-Mediated Carboxylation: Use of Two Nitrogen Atoms of the Pyrazole Group

Abstract

Carboxylation of 1-arylpyrazole derivatives was developed using a ruthenium-catalyzed <i>ortho</i> silylation in conjunction with fluoride-mediated carboxylation with carbon dioxide. The two nitrogen atoms of pyrazole play crucial roles in promoting <i>ortho</i> silylation via the formation of a five-membered ruthenacycle and in accelerating aryl anion formation by lowering the electron density of the aromatic ring.